Identification
NameCaffeine
Accession NumberDB00201  (APRD00673)
TypeSmall Molecule
GroupsApproved
Description

A methylxanthine naturally occurring in some beverages and also used as a pharmacological agent. Caffeine's most notable pharmacological effect is as a central nervous system stimulant, increasing alertness and producing agitation. It also relaxes smooth muscle, stimulates cardiac muscle, stimulates diuresis, and appears to be useful in the treatment of some types of headache. Several cellular actions of caffeine have been observed, but it is not entirely clear how each contributes to its pharmacological profile. Among the most important are inhibition of cyclic nucleotide phosphodiesterases, antagonism of adenosine receptors, and modulation of intracellular calcium handling.

Structure
Thumb
Synonyms
1-methyltheobromine
1,3,7-trimethyl-2,6-dioxopurine
1,3,7-trimethylpurine-2,6-dione
1,3,7-trimethylxanthine
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion
7-methyltheophylline
Anhydrous caffeine
Cafeína
Caféine
Caffeinum
Coffein
Coffeinum
Guaranine
Koffein
Mateína
Methyltheobromine
teína
Thein
Theine
External IDs Fema no. 2224 / NSC-5036
Product Ingredients
IngredientUNIICASInChI KeyDetails
Caffeine citrateU26EO4675Q 69-22-7RCQXSQPPHJPGOF-UHFFFAOYSA-NDetails
Product Images
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CafcitInjection20 mg/mLIntravenousWest Ward Pharmaceutical2008-11-04Not applicableUs
CafcitInjection20 mg/mLIntravenousBedford Pharmaceuticals2008-11-042016-04-30Us
CafcitSolution20 mg/mLOralBedford Pharmaceuticals2008-11-042016-05-29Us
Diurette Water PillsTablet200 mgOralAlva Amco Pharmacal Companies, Inc.Not applicableNot applicableCanada
PeyonaInjection, solution; Solution20 mg/mlIntravenous; OralChiesi Farmaceutici Sp A2009-07-02Not applicableEu
PeyonaInjection, solution; Solution20 mg/mlIntravenous; OralChiesi Farmaceutici Sp A2009-07-02Not applicableEu
Spirit (chewable Squares)Wafer60 mgOralWarner Lambert Canada Inc.Not applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Caffeine CitrateInjection, solution20 mg/mLIntravenousAmerican Regent2007-09-10Not applicableUs
Caffeine CitrateInjection, solution20 mg/mLIntravenousFresenius Kabi2009-11-19Not applicableUs
Caffeine CitrateSolution20 mg/mLOralExela Pharma Sciences, Llc.2006-09-21Not applicableUs
Caffeine CitrateInjection20 mg/mLIntravenousSun Pharma Global FZE2009-10-01Not applicableUs
Caffeine CitrateSolution20 mg/mLOralAPP Pharmaceuticals, Inc.2009-11-19Not applicableUs
Caffeine CitrateSolution20 mg/mLOralExela Pharma Sciences, Llc.2006-09-21Not applicableUs
Caffeine CitrateSolution20 mg/mLOralRemedy Repack2013-10-042016-12-28Us
Caffeine CitrateSolution20 mg/mLIntravenousSagent Pharmaceuticals2012-09-15Not applicableUs
Caffeine CitrateSolution20 mg/mLOralSun Pharma Global FZE2009-10-01Not applicableUs
Caffeine CitrateInjection20 mg/mLIntravenousExela Pharma Sciences, Llc.2006-09-21Not applicableUs
Caffeine CitrateInjection, solution20 mg/mLIntravenousAuro Medics Pharma Llc2015-09-22Not applicableUs
Caffeine CitrateSolution20 mg/mLOralSagent Pharmaceuticals2012-09-15Not applicableUs
Caffeine CitrateInjection20 mg/mLIntravenousExela Pharma Sciences, Llc.2006-09-21Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
357 Super MagnumTablet, multilayer200 1/1OralKing Richard Promotions Dba Dbi2016-05-19Not applicableUs
AlertTablet, film coated200 mg/1OralTime Cap Laboratories2011-11-30Not applicableUs
AlertTablet200 mg/1OralDolgencorp1992-11-21Not applicableUs
Alert Aid Caffeine Capsules 175mgCapsule175 mgOralSun Products Corporation1991-12-312004-03-11Canada
Alert Aid Caffeine Tablets 175mgTablet175 mgOralSun Products Corporation1991-12-312004-03-11Canada
Alert Alertness AidTablet200 mg/1OralLnk International, Inc.1992-11-21Not applicableUs
Alert Tab 100mgTablet100 mgOralNutribon (1986) Inc.1995-12-311996-09-30Canada
Alertness AidTablet, coated200 mg/1OralWe Care Distributor Inc.2016-03-07Not applicableUs
Alertness AidTablet200 mg/1OralChain Drug Consortium1996-11-21Not applicableUs
Alertness AidTablet200 mg/1OralCardinal Health1996-11-21Not applicableUs
Alertness Aid Maximum StrengthTablet200 mg/1OralHarmon Store Inc.1996-11-21Not applicableUs
Alertness Aid Stay AwakeTablet200 mg/1OralHealthlife of Usa2017-05-31Not applicableUs
Allertness AidTablet200 mg/1OralSelect Corporation2012-10-15Not applicableUs
Allertness AidTablet200 mg/1OralChain Drug Consortium2014-11-03Not applicableUs
Awake Maximum StrengthTablet, film coated200 mg/1OralWalgreen1998-04-14Not applicableUs
Awake Maximum StrengthTablet, film coated200 mg/1OralBetter Living Brands1998-04-14Not applicableUs
CaffeineTablet200 mg/1OralAAA Pharmaceutical, Inc.2012-12-15Not applicableUs
CaffeineTablet200 mg/1OralCvs Health1992-11-21Not applicableUs
CaffeineTablet200 mgOralAdded Dimensions1996-12-202006-09-25Canada
Caffeine 200 mgTablet, multilayer200 mg/200mgOralUltr Atab Laboratories, Inc.2016-04-052017-04-21Us
Caffeine Maximum StrengthTablet, film coated200 mg/1OralCvs Health1998-04-14Not applicableUs
Circle K NosnoozeTablet200 mg/1OralLil' Drug Store Products, Inc.2014-11-01Not applicableUs
Conrx AlertTablet200 mg/1OralEagle Distributors,Inc.2013-02-15Not applicableUs
Destim - Tab 200mgTablet200 mgOralD & E Pharmaceuticals Inc.1995-12-312009-06-08Canada
Diurex UltraTablet, film coated100 mg/1OralAlva Amco Pharmacal Companies, Inc.2005-09-01Not applicableUs
Diurex WatercapsTablet, film coated200 mg/1OralAlva Amco Pharmacal Companies, Inc.2009-04-15Not applicableUs
Drowz Away Maximum StrengthTablet200 mg/1OralCare One (American Sales Company)2014-03-05Not applicableUs
Drowz Away Maximum StrengthTablet200 mg/1OralCare One (American Sales Company)2010-08-31Not applicableUs
Equaline Stay AwakeTablet200 mg/1OralSupervalu2004-08-30Not applicableUs
Good Neighbor Pharmacy Stay AwakeTablet200 mg/1OralAmerisource Bergen2001-07-16Not applicableUs
Good Sense Stay AwakeTablet200 mg/1OralL. Perrigo Company1993-03-23Not applicableUs
Health Mart Stay AwakeTablet200 mg/1OralMc Kesson2011-11-21Not applicableUs
Healthy Accents Stay AwakeTablet200 mg/1OralDza Brands,2008-02-04Not applicableUs
Jet Alert Double StrengthTablet, coated200 mg/1OralBell International Laboratories2014-11-26Not applicableUs
Jet Alert Regular StrengthTablet, coated100 mg/1OralBell International Laboratories2014-12-01Not applicableUs
Jet-alert Maximum Strength Alertness AidCapsule, liquid filled200 mg/1OralBell International Laboratories2014-11-262016-01-09Us
Leader Alertness AidTablet200 mg/1OralCardinal Health1994-02-10Not applicableUs
Lil Drug Store NosnoozeTablet200 mg/1OralLil' Drug Store Products, Inc.2011-02-08Not applicableUs
Lil Drug Store NosnoozeTablet200 mg/1OralLil' Drug Store Products, Inc.2011-02-08Not applicableUs
Nano PpcCream5 mg/1000mLTopicalYBK Investment, INC2013-10-15Not applicableUs
Nodoz Maximum Strength Alertness AidTablet, coated200 mg/1OralGlaxo Smith Kline Consumer Healthcare Holdings (Us) Llc2009-12-31Not applicableUs
Pep-back Peak PerformanceTablet, film coated200 mg/1OralAlva Amco Pharmacal Companies, Inc.2007-03-28Not applicableUs
Pep-back UltraTablet, film coated200 mg/1OralAlva Amco Pharmacal Companies, Inc.1993-04-08Not applicableUs
Phenfree Caffeine 100mg CapsulesCapsule100 mgOralUpper 49 Th Imports Inc.1999-07-012004-09-09Canada
Smart Sense Stay AwakeTablet200 mg/1OralKmart Corporation2010-12-16Not applicableUs
Sohmed Alertness AidTablet200 mg/1OralSOHM Inc.2013-08-25Not applicableUs
Stay Alert AidTablet200 mg/1OralRite Aid1992-11-21Not applicableUs
Stay Alert Alertness AidTablet200 mg/1OralL&R Distributors, Inc.1996-11-21Not applicableUs
Stay AwakeTablet200 mg/1OralH.E.B.1996-03-25Not applicableUs
Stay AwakeTablet, coated200 mg/1OralAllegiant Health2014-07-01Not applicableUs
Stay AwakeTablet200 mg/1OralPublix Supermarkets, Inc.1998-01-06Not applicableUs
Stay AwakeTablet200 mg/1OralNash Finch1992-11-21Not applicableUs
Stay AwakeTablet200 mg/1OralHyvee1996-05-28Not applicableUs
Stay AwakeTablet200 mg/1OralWestern Family Foods2014-02-28Not applicableUs
Stay AwakeTablet200 mg/1OralFred's2014-03-28Not applicableUs
Stay AwakeTablet200 mg/1OralKroger1994-06-17Not applicableUs
Stay AwakeTablet200 mg/1OralSalado Sales, Inc.1996-11-21Not applicableUs
Stay AwakeTablet200 mg/1OralGreenbrier International, Inc.1996-11-21Not applicableUs
Stay AwakeTablet200 mg/1OralMc Kesson (Health Mart)1996-11-21Not applicableUs
Stay AwakeTablet200 mg/1OralWestern Family Foods2010-07-01Not applicableUs
Stay AwakeTablet200 mg/1OralWalmart Stores1996-11-21Not applicableUs
Stay AwakeTablet200 mg/1OralSupervalu1992-11-21Not applicableUs
Stay AwakeTablet, coated200 mg/1OralMarc Glassman, Inc.2014-07-01Not applicableUs
Stay AwakeTablet200 mg/1OralChain Drug Marketing Association1996-11-21Not applicableUs
Stay AwakeTablet200 mg/1OralChain Drug Marketing Association2014-06-13Not applicableUs
Stay AwakeTablet200 mg/1OralMeijer2011-08-01Not applicableUs
Stay AwakeTablet200 mg/1OralArmy + Air Force Exchange Service1996-11-21Not applicableUs
Stay AwakeTablet200 mg/1OralMajor1992-11-21Not applicableUs
Stay AwakeTablet200 mg/1OralSunmark (Mckesson)1996-11-21Not applicableUs
Stay AwakeTablet200 mg/1OralNational Distribution Network (Smart Choice)2014-05-30Not applicableUs
Stay AwakeTablet200 mg/1OralFred's2013-03-01Not applicableUs
Stay AwakeTablet, film coated200 mg/1OralRite Aid1998-04-14Not applicableUs11822 0691 01 nlmimage10 52392909
Stay AwakeTablet200 mg/1OralKinray2013-05-09Not applicableUs
Stay AwakeTablet200 mg/1OralWin Co Foods, Llc,1996-11-21Not applicableUs
Stay AwakeTablet200 mg/1OralValu Merchandisers Company (Best Choice)2014-04-30Not applicableUs
Stay Awake Maximum StrengthTablet200 mg/1OralBetter Living Brands1992-11-21Not applicableUs
Stay Awake Maximum StrengthTablet200 mg/1OralValu Merchandisers Company (Best Choice)2010-09-21Not applicableUs
Stay Awake Maximum StrengthTablet200 mg/1OralGreat Lakes Wholesale, Marketing, and Sales, Inc.1992-11-21Not applicableUs
Stay Awake Maximum StrengthTablet, film coated200 mg/1OralSupervalu1998-04-14Not applicableUs
Stay Awake Maximum StrengthTablet200 mg/1OralWalgreen1996-11-21Not applicableUs
Sugarloaf Spring Caffeine, Caffeinated Spring WaterLiquid50 mgOralSugarloaf Spring Rain International Ltd.1998-10-152002-07-09Canada
Sunmark Stay AwakeTablet200 mg/1OralMc Kesson2003-08-21Not applicableUs
Topcare Stay Awake Maximum StrengthTablet200 mg/1OralTopco Associates1993-12-14Not applicableUs
VivarinTablet200 mg/1OralMeda Pharmaceuticals Ltd2012-01-15Not applicableUs
VivarinTablet200 mg/1OralNavajo Manuracturing Company2016-09-21Not applicableUs
VivarinTablet200 mg/1OralMeda Pharmaceuticals Ltd2014-06-15Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Caffeine and Sodium BenzoateInjection, solution125 mg/mLIntramuscular; IntravenousAmerican Regent1993-02-01Not applicableUs
Diurex UltimateTablet, film coated100 mg/1OralAlva Amco Pharmacal Companies, Inc.2015-10-31Not applicableUs
Diurex Water Pills XplTablet, film coated100 mg/1OralAlva Amco Pharmacal Companies, Inc.2016-08-17Not applicableUs
International Brands
NameCompany
CaffedrineNot Available
DexitacNot Available
DurvitanNot Available
EnerjetsNot Available
No-DozNot Available
Pep-BackNot Available
Quick PepNot Available
Wake-UpNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
(extra Strength) Acetaminophen, Caffeine & 8mg Codeine Phosphate CapletsTabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1998-07-222002-07-31Canada
217TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1910-12-311998-04-21Canada
217 Strong TabTabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1973-12-311998-04-21Canada
222 TabletsTabletOralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1951-12-312015-08-17Canada
282 Mep TabTabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1959-12-311998-08-14Canada
282 TabTabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1951-12-311998-04-21Canada
282 TabletsTabletOralPendopharm Division Of De Pharmascience Inc1998-11-01Not applicableCanada
292 TabTabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1951-12-311998-08-14Canada
292 TabletsTabletOralPendopharm Division Of De Pharmascience Inc1998-10-01Not applicableCanada
692 TabTabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1986-02-131998-04-21Canada
692 TabletTabletOralLioh Inc.1998-09-012006-08-25Canada
7 Select Migraine FormulaTablet, film coatedOral7 Eleven2014-05-09Not applicableUs
999 Ganmaoling ColdCapsuleOralKingsway2012-07-30Not applicableUs
A & C Tablets With Codeine 15mgTabletOralD.C. Labs Limited1971-12-312003-07-11Canada
A & C Tablets With Codeine 30mgTabletOralD.C. Labs Limited1971-12-312003-07-11Canada
A.C. & C. 8 mgTabletOralLaboratoires Confab IncNot applicableNot applicableCanada
A.C. & C. 8mgTabletOralWestcan Pharmaceuticals Ltd.Not applicableNot applicableCanada
A.C.& C TabletsTabletOralPharmascience Inc1993-12-31Not applicableCanada
Ac and C Tab 1/8grTabletOralPharmascience Inc1983-12-312013-09-30Canada
Ac&c TabletsTabletOralPharmascience Inc2008-06-11Not applicableCanada
Acet 2TabletOralPharmascience Inc1994-12-312013-05-09Canada
Acet 3TabletOralPharmascience Inc1994-12-312013-05-09Canada
Acetaminophen 300 Mg With 15 Mg Caffeine and 8 Mg Codeine PhosphateTabletOralVita Health Products Inc1996-10-11Not applicableCanada
Acetaminophen 300mg, Caffeine & CodeineTabletOralTanta Pharmaceuticals IncNot applicableNot applicableCanada
Acetaminophen 325 C & CTabletOralTechnilab Pharma Inc.Not applicableNot applicableCanada
Acetaminophen 325 Mg Caffeine and CodeineTabletOralTanta Pharmaceuticals IncNot applicableNot applicableCanada
Acetaminophen 325 Mg With 15 Mg Caffeine and 8 Mg Codeine PhosphateTabletOralVita Health Products Inc1987-12-31Not applicableCanada
Acetaminophen 500 Mg Compound Tablets With CodeineTabletOralPharmascience Inc1984-12-312016-10-28Canada
Acetaminophen 500 Mg With 15 Mg Caffeine and 8 Mg Codeine PhosphateTabletOralVita Health Products Inc1987-12-312014-07-28Canada
Acetaminophen 500mg and Caffeine 65mgTabletOralPharmetics (2011) Inc.2007-06-21Not applicableCanada
Acetaminophen 500mg, Caffeine and 8mg Codeine PhosphateTabletOralPharmetics (2011) Inc.Not applicableNot applicableCanada
Acetaminophen Caffeine & 8mg Cod Phos TabTabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1986-12-312002-07-31Canada
Acetaminophen Caffeine & 8mg Cod. Phos. TabTabletOralNovopharm Limited1992-12-312012-12-05Canada
Acetaminophen Compound Tablets With Codeine 8mgTabletOralD.C. Labs Limited1984-12-312005-07-19Canada
Acetaminophen Headache Ultra ReliefTabletOralApotex Corporation2008-09-26Not applicableCanada
Acetaminophen Relief Regular StrengthTabletOralJamp Pharma CorporationNot applicableNot applicableCanada
Acetaminophen Ultra Relief Extra StrengthTabletOralJamp Pharma CorporationNot applicableNot applicableCanada
Acetaminophen W Codeine TabTabletOralPharmascience Inc1983-12-312013-09-30Canada
Acetaminophen With Codeine - CapletTabletOralTeva1997-10-28Not applicableCanada
Acetaminophen-caffeine-codeineTabletOralLaboratoires Confab IncNot applicableNot applicableCanada
Acetaminophen, Butalbital and CaffeineTabletOralStat Rx USA1988-02-16Not applicableUs
Acetaminophen, Caffeine & 8mg Codeine PhosphateTabletOralPharmascience Inc1998-12-17Not applicableCanada
Acetaminophen, Caffeine & 8mg Codeine Phosphate TabletsTabletOralJamp Pharma Corporation2004-06-25Not applicableCanada
Acetaminophen, Caffeine & CodeineTabletOralPharmascience Inc1993-12-31Not applicableCanada
Acetaminophen, Caffeine & Codeine TabletsTabletOralPharmascience IncNot applicableNot applicableCanada
Acetaminophen, Caffeine and 8 Mg Of Codeine Phosphate TabletsTabletOralPharmetics (2011) Inc.2005-01-20Not applicableCanada
Acetaminophen, Caffeine and Dihydrocodeine BitartrateTabletOralLarken Laboratories, Inc.2016-10-04Not applicableUs
Acetaminophen, Caffeine, and 8mg Of Codeine Phosphate TabletsTabletOralPharmetics (2011) Inc.2004-07-16Not applicableCanada
Acetaminophen, Caffeine, Dihydrocodeine BitartrateCapsuleOralXspire Pharma2015-08-05Not applicableUs
Acetaminophene Codeine Et Cafeine CapletsTabletOralLaboratoire Riva Inc1993-12-31Not applicableCanada
Acetaminophene Codeine Et Cafeine FortTabletOralLaboratoire Riva Inc1993-12-31Not applicableCanada
Acetylsalicylic Acid Caffeine & 8mg Cod PhosTabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1970-12-311997-10-14Canada
Acetylsalicylic Acid, Caffeine & 8 Mg Codeine Phosphate TabletsTabletOralJamp Pharma Corporation2004-06-25Not applicableCanada
Acetylsalicylic Acid, Caffeine and 8mg Codeine PhosphateTabletOralPharmetics (2011) Inc.1970-12-31Not applicableCanada
Ache and Pain Relief To GoPowderOralBreakthrough Products Inc.2012-10-01Not applicableUs
Added Strength Pain RelieverTablet, film coatedOralBetter Living Brands1992-11-17Not applicableUs
Adults Acetaminophen and Caffeine Pain Reliever Fever ReducerTabletOralGenvion Corporation2016-05-05Not applicableUs
Alka-seltzer Morning ReliefTablet, effervescentOralBayer Inc Consumer Care2002-09-102006-07-28Canada
AnacinCapsule, coatedOralInsight Pharmaceuticals2009-06-29Not applicableUs
Anacin AFTablet, coatedOralInsight Pharmaceuticals2009-06-29Not applicableUs
Anacin CapletsTabletOralWyeth Ltd.1945-12-312011-08-05Canada
Anacin EsTablet, coatedOralInsight Pharmaceuticals2009-07-07Not applicableUs
Anacin Extra StrengthTabletOralPaladin Labs Inc2011-06-16Not applicableCanada
Anacin Extra Strength CapletsTabletOralWyeth Ltd.1994-12-312011-08-05Canada
Anacin Extra Strength TabletTabletOralWyeth Ltd.1994-12-312011-08-05Canada
Anacin TabletTabletOralWyeth Ltd.1993-12-312011-08-05Canada
Anacin With Codeine TabTabletOralWhitehall Robins Inc.1965-12-312000-07-26Canada
Antidol TabletsTabletOralLes Produits Gerbex Inc.1988-12-312007-12-28Canada
Apo-acetaco #1TabletOralApotex CorporationNot applicableNot applicableCanada
Ara Menstrual CompleteTabletOralAra Avanti Rx Analytics IncNot applicableNot applicableCanada
Arco Pain TabTabletOralLaboratoire Romilo1979-12-311999-08-18Canada
Arthriten Inflammatory Pain FormulaTablet, film coatedOralAlva Amco Pharmacal Companies, Inc.2012-07-23Not applicableUs
Asa and CaffeineTabletOralTherapharma Inc.Not applicableNot applicableCanada
Asa-caffeine-codeineTabletOralLaboratoires Confab IncNot applicableNot applicableCanada
Asa, Caffeine & 8mg Codeine PhosphateTabletOralCanapharm Manufacturing Inc2000-03-132006-08-25Canada
Ascomp With CodeineCapsuleOralNexgen Pharma, Inc.2001-11-30Not applicableUs
Aspirin Rapid ReliefTabletOralBayer Inc Consumer CareNot applicableNot applicableCanada
Aspirin, Caffeine, and Dihydrocodeine BitartrateCapsuleOralCaraco Pharmaceutical Laboratories, Ltd.2012-10-01Not applicableUs
Atasol 15TabletOralChurch & Dwight Company, Inc.1975-12-31Not applicableCanada
Atasol 30TabletOralChurch & Dwight Company, Inc.1975-12-31Not applicableCanada
Atasol 8TabletOralChurch & Dwight Company, Inc.1975-12-31Not applicableCanada
Back and Body Extra StrengthTabletOralGreenbrier International, Inc.2004-04-12Not applicableUs
Backaid Inflammatory Pain FormulaTablet, film coatedOralAlva Amco Pharmacal Companies, Inc.2012-10-22Not applicableUs
Bayer Am Extra StengthTabletOralBayer Health Care Llc, Consumer Care2010-04-152017-01-19Us
Bayer Back and Body Extra StrengthTabletOralBayer Health Care Llc.2015-01-12Not applicableUs
Bayer Headache ReliefCapsuleOralBayer2012-06-01Not applicableUs
Bayer Migraine FormulaTabletOralBayer Health Care Llc, Consumer Care2012-06-26Not applicableUs
BcPowderOralMedtech Laboratories, Inc.2012-06-01Not applicableUs
Bc ArthritisPowderOralMedtech Laboratories, Inc.2012-06-01Not applicableUs
Bc CherryPowderOralLil' Drug Store Products, Inc.2014-03-01Not applicableUs
Berkley and Jensen Migraine FormulaTablet, film coatedOralBJWC2014-02-21Not applicableUs
Berkley and Jensen Migraine ReliefTablet, film coatedOralBJWC2004-06-10Not applicableUs
Bi Electro Extra StrengthTabletOralGenomma Lab2015-01-08Not applicableUs
BlowfishTablet, effervescentOralRally Labs Llc2011-07-23Not applicableUs
Butalbital Acetaminophen and CaffeineTabletOralLake Erie Medical Dba Quality Care Produts Llc2010-10-11Not applicableUs
Butalbital CompoundTabletOralMajor2000-01-28Not applicableUs
Butalbital, Acetaminophen and CaffeineTabletOralKaiser Foundations Hospitals2013-08-19Not applicableUs
Butalbital, Acetaminophen and Caffeine PlusTabletOralStat Rx USA2003-08-25Not applicableUs
Butalbital, Acetaminophen and Caffeine With Codeine PhosphateCapsuleOralWest Ward Pharmaceutical2001-03-21Not applicableUs
Butalbital, Acetaminophen, and CaffeineCapsuleOralWest Ward Pharmaceutical1998-10-28Not applicableUs
Butalbital, Acetaminophen, CaffeineTabletOralRemedy Repack2011-11-102016-11-05Us
Butalbital, Acetaminophen, Caffeine and Codeine PhosphateCapsuleOralBreckenridge Pharmaceutical, Inc.2004-07-01Not applicableUs51991 0073 01 nlmimage10 ee1ff71f
Butalbital, Acetaminophen, Caffeine, and Codeine PhosphateCapsuleOralActavis Pharma Company2013-07-29Not applicableUs
Butalbital, Acetominophen and CaffeineTabletOralbryant ranch prepack2009-04-27Not applicableUs64980 0155 01 nlmimage10 6733b3dd
Butalbital, Aspirin and CaffeineTabletOralWest Ward Pharmaceutical1979-06-05Not applicableUs
Butalbital, Aspirin and Caffeine TabletsTabletOralQualitest1979-06-052015-12-29Us
Butalbital, Aspirin, and CaffeineCapsuleOralActavis Pharma Company2003-10-06Not applicableUs
Butalbital, Aspirin, Caffeine and Codeine PhosphateCapsuleOralLannett Company, Inc.1998-08-31Not applicableUs
Butalbital, Aspirin, Caffeine, and Codeine PhosphateCapsuleOralMayne Pharma2015-10-30Not applicableUs
C T Acetylsalicylic Acid Codeine and Caf TabTabletOralPharmavite Laboratories (1987) Inc.1995-12-312006-07-27Canada
C-2 Buffered With CodeineTabletOralPharmascience Inc1999-06-152016-10-28Canada
C2 Buffered TabTabletOralWampole Brands, A Division Of Pangeo Pharma (Canada) Inc.1986-12-311996-09-09Canada
C2 Buffered With Codeine TabTabletOralWampole Brands, A Division Of Pangeo Pharma (Canada) Inc.1986-12-311999-06-15Canada
C2 Tab With CodeineTabletOralWampole Brands, A Division Of Pangeo Pharma (Canada) Inc.1986-12-311996-09-09Canada
CafergotTabletOralKaiser Foundations Hospitals2011-04-21Not applicableUs00781 5405 01 nlmimage10 4a132549
Cafergot SupSuppositoryRectalNovartis1990-12-312006-11-13Canada
Cafergot TabTabletOralNovartis1951-12-312014-03-31Canada
Calmine TabTabletOralLes Laboratoires Vachon Inc.1989-12-312008-02-13Canada
CapacetCapsuleOralMagna Pharmaceuticals2011-05-02Not applicableUs
Care One Headache Relief Added StrengthTablet, film coatedOralAmerican Sales Company2004-04-13Not applicableUs
Care One Migraine ReliefTablet, film coatedOralAmerican Sales Company2004-04-13Not applicableUs
Careline Perfect Care BbCreamTopicalCosmopharm Ltd.2015-09-17Not applicableUs
Circle K Headache ReliefTabletOralLil' Drug Store Products, Inc.2014-11-01Not applicableUs
CitramonTabletOralBorisovskiy Zavod Medicinskikh Preparatov Jsc1996-06-26Not applicableUs
Cold Remedy Gan Mao LingTabletOralInternational Nature Nutraceuticals2003-07-28Not applicableUs
Comfort-timeTablet, film coatedOralTime Cap Laboratories2011-11-30Not applicableUs
Complete Menstrual ReliefTabletOralGood Sense (Geiss, Destin & Dunn, Inc.)2012-01-16Not applicableUs
Conrx Pain RelieverTabletOralEagle Distributors,Inc.2013-02-15Not applicableUs
CorytabTabletOralLes Laboratoires Vachon Inc.1988-12-312009-02-24Canada
CotabsTabletOralPharmavite Laboratories (1987) Inc.1961-12-312000-08-18Canada
Darvon N Compound Pulvule 405CapsuleOralEli Lilly & Co. Ltd.1973-12-311999-08-11Canada
Dg Health Headache Relief Added StrengthTablet, film coatedOralDolgencorp2010-03-10Not applicableUs
Dg Health Migraine ReliefTablet, coatedOralDolgencorp2009-12-04Not applicableUs
Dihydrocodeine Bitartrate, Acetaminophen and CaffeineTabletOralPhysicians Total Care, Inc.2008-05-20Not applicableUs
Diurex Water PillsTablet, coatedOralAlva Amco Pharmacal Companies, Inc.2005-05-15Not applicableUs
Dolomine 37TabletOralFrega Inc.1989-12-312008-02-13Canada
Dristan CapsulesCapsuleOralWhitehall Robins Inc.1993-12-311999-08-04Canada
Emercidin D TabTabletOralPharmetics (2011) Inc.1989-12-312001-03-30Canada
Emertabs TabTabletOralPharmetics (2011) Inc.1989-12-311999-08-13Canada
Equaline Headache Formula Added StrengthTablet, film coatedOralSupervalu2004-08-30Not applicableUs
Equaline Migraine FormulaTabletOralSupervalu2004-09-03Not applicableUs
Equate Migraine ReliefTablet, film coatedOralWalmart Stores2002-04-16Not applicableUs
Ergodryl CapCapsuleOralErfa Canada 2012 Inc1964-12-312013-07-09Canada
ErgotamineTablet, film coatedOralWest Ward Pharmaceutical2004-09-17Not applicableUs
Ergotamine Tartrate and CaffeineTabletOralKaiser Foundations Hospitals2010-06-25Not applicableUs
EsgicCapsuleOralForest Laboratories1997-04-092016-11-08Us
ExaprinTabletOralHART Health1987-01-20Not applicableUs
ExcedrinTabletOralBristol Myers Squibb1986-12-312004-08-05Canada
Excedrin Extra StrengthTablet, film coatedOralNovartis2006-09-272017-04-14Us
Excedrin Extra Strength CapletsTablet, film coatedOralGlaxo Smith Kline Consumer Healthcare Holdings (Us) Llc2013-01-16Not applicableUs
Excedrin Extra Strength GeltabsTablet, coatedOralGlaxo Smith Kline Consumer Healthcare Holdings (Us) Llc2011-09-13Not applicableUs
Excedrin Extra Strength Pain RelieverTablet, film coatedOralGlaxo Smith Kline Consumer Healthcare Holdings (Us) Llc2006-09-27Not applicableUs
Excedrin Menstrual CompleteCapsule, gelatin coatedOralNovartis2009-12-10Not applicableUs
Excedrin MigraineTablet, film coatedOralNovartis2010-02-15Not applicableUs
Excedrin Migraine GeltabsTablet, coatedOralNovartis2011-09-13Not applicableUs
Excedrin Mild Headache CapletsTablet, coatedOralNovartis2014-09-242017-04-14Us
Excedrin Tension HeadacheTablet, film coatedOralNovartis2005-10-312017-04-14Us
Excedrin Tension Headache Pain RelieverTablet, film coatedOralNovartis2014-06-27Not applicableUs
Exdol 15tabTabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1977-12-311998-04-21Canada
Exdol 30tabTabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1977-12-311998-04-21Canada
Exdol 8 TabTabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1977-12-311998-04-21Canada
Exdol-15TabletOralPharmascience Inc1998-09-012016-07-14Canada
Exdol-30TabletOralPharmascience Inc1998-09-012016-07-14Canada
Exdol-8TabletOralPharmascience Inc1998-08-012016-07-14Canada
Extra Pain ReliefTablet, film coatedOralTime Cap Laboratories2013-11-01Not applicableUs
Extra Strenght Headache ReliefTabletOralSpirit Pharmaceuticals, Llc2016-08-18Not applicableUs
Extra Strength Back and BodyCapsuleOralDolgencorp2004-04-122016-09-13Us
Extra Strength Contac Plus Cold Nasal CongestionTabletOralGlaxosmithkline IncNot applicableNot applicableCanada
Extra Strength Headache ReliefCapsule, gelatin coatedOralTarget Corporation.2009-01-09Not applicableUs
Extra Strength Menstrual CompleteTabletOralVita Health Products Inc2013-01-142014-07-28Canada
Extra Strength MidolTabletOralBayer Inc Consumer Care1996-10-012007-08-02Canada
Extra Strength Midol ReliefTabletOralBayer Inc Consumer CareNot applicableNot applicableCanada
Extra Strength Pain RelieverCapsule, gelatin coatedOralRite Aid2009-01-09Not applicableUs
Family Wellness Migraine ReliefTablet, film coatedOralFamily Dollar Services2013-07-20Not applicableUs
FioricetCapsuleOralActavis Pharma Company2013-07-29Not applicableUs
Fioricet With CodeineCapsuleOralWatson Pharma, Inc.2013-07-29Not applicableUs
FiorinalCapsuleOralActavis Pharma Company1976-05-04Not applicableUs
Fiorinal C1/2CapsuleOralTribute Pharmaceuticals1970-12-31Not applicableCanada
Fiorinal C1/4CapsuleOralTribute Pharmaceuticals1970-12-31Not applicableCanada
Fiorinal TabTabletOralNovartis1973-12-312009-08-20Canada
Fiorinal With CodeineCapsuleOralActavis Pharma Company1990-10-26Not applicableUs
First Aid Shot Therapy Hangover ReliefSolutionOralFirst Aid Beverages, Inc.2015-02-01Not applicableUs
First Aid Shot Therapy Pain ReliefLiquidOralFirst Aid Beverages, Inc.2013-09-05Not applicableUs
Formu Care Pain Reliever Added StrengthTablet, film coatedOralAccess Business Group1998-07-20Not applicableUs
Ganmaoling 999GranuleOralKingsway Trading2012-06-30Not applicableUs
Good Neighbor Pharmacy Headache ReliefTablet, film coatedOralAmerisource Bergen1992-06-16Not applicableUs
Good Neighbor Pharmacy Migraine ReliefTablet, film coatedOralAmerisource Bergen2002-05-13Not applicableUs
Good Sense Headache Formula Added StrengthTablet, film coatedOralL. Perrigo Company1992-01-20Not applicableUs
Good Sense Migraine FormulaTablet, film coatedOralL. Perrigo Company2002-04-17Not applicableUs
GoodysPowderOralGlaxo Smith Kline Consumer Heathcare Lp2010-12-082015-12-31Us
Goodys Cool OrangePowderOralLil' Drug Store Products, Inc.2014-03-01Not applicableUs
Goodys Cool Orange HeadachePowderOralMedtech Laboratories, Inc.2012-06-01Not applicableUs
Goodys Extra StrengthPowderOralMedtech Laboratories, Inc.2013-11-01Not applicableUs
Goodys Extra Strength Headache Mixed Fruit BlastPowderOralMedtech Laboratories, Inc.2015-08-01Not applicableUs
Goodys Headache Relief ShotLiquidOralMedtech Laboratories, Inc.2013-02-11Not applicableUs
Goodys Migraine ReliefCapsule, coatedOralMedtech Laboratories, Inc.2012-11-01Not applicableUs
Goodys PM Pain RelieverCapsule, coatedOralMedtech Laboratories, Inc.2012-07-13Not applicableUs
Gravergol CapsulesCapsuleOralCan Med Pharma Inc.1957-12-312011-12-07Canada
Green Guard Pain and Ache ReliefTabletOralUnifirst First Aid2008-12-30Not applicableUs
Handy Solutions Headache Pain ReliefTabletTopicalNavajo Manuracturing Company2016-10-21Not applicableUs
Harris Teeter Migraine ReliefTablet, film coatedOralHarris Teeter2016-03-18Not applicableUs
Headache Formula Added StrengthTablet, film coatedOralKroger1997-01-30Not applicableUs
Headache Formula Extra StrengthTablet, film coatedOralArmy + Air Force Exchange Service1992-11-17Not applicableUs
Headache ReliefTabletOralTarget Corporation.2014-11-30Not applicableUs
Headache Relief Added StrengthTablet, film coatedOralMedicine Shoppe International1992-04-09Not applicableUs
Headache Relief Extra StrengthTabletOralWalgreens2014-09-30Not applicableUs
Headache Relief MildTabletOralMeijer2015-03-01Not applicableUs
Headache Relief To GoPowderOralBreakthrough Products Inc.2012-10-01Not applicableUs
Health Mart Migraine FormulaTablet, film coatedOralMc Kesson2013-01-29Not applicableUs
Health Mart Migraine ReliefTablet, film coatedOralMc Kesson2014-04-22Not applicableUs
Healthy Accents Headache Relief Added StrengthTablet, film coatedOralDza Brands,2008-02-11Not applicableUs
Healthy Accents Migraine FormulaTablet, film coatedOralDza Brands,2008-03-10Not applicableUs
Herbopyrine Tab 325mgTabletOralHerbes Universelles Inc.1987-12-312009-07-15Canada
Instantine - TabletsTabletOralBayer Inc Consumer Care1976-12-312007-08-02Canada
Instantine TabTabletOralSterling Winthrop Inc.1992-12-311996-09-10Canada
Isometheptene Mucate, Caffeine, and AcetaminophenTabletOralXspire Pharma2010-06-01Not applicableUs
Leader Headache Formula Added StrengthTablet, film coatedOralCardinal Health1997-04-02Not applicableUs
Leader Migraine FormulaTabletOralCardinal Health2002-05-16Not applicableUs
Leader Migraine ReliefTablet, film coatedOralCardinal Health2017-02-16Not applicableUs
Lil Drug Store Headache Relief Extra StrengthTabletOralLil' Drug Store Products, Inc.2011-01-27Not applicableUs
MadelonTabletOralLes Laboratoires Du Saint Laurent E.H. Ltee1993-12-31Not applicableCanada
MargesicCapsuleOralMarnel Pharmaceuticals, Llc1994-06-01Not applicableUs
Maximum Strength Menstrual CompleteCapsule, liquid filledOralRite Aid2001-06-14Not applicableUs
Medi First Pain ReliefTabletOralUnifirst First Aid2008-12-30Not applicableUs
Medi First Plus Pain ZapperTabletOralUnifirst First Aid2008-12-30Not applicableUs
Medique Back Pain OffTablet, film coatedOralUnifirst First Aid2008-12-30Not applicableUs
Medique Pain OffTablet, film coatedOralUnifirst First Aid2008-12-30Not applicableUs
Megral TabsTabletOralGlaxo Wellcome1989-12-312001-03-01Canada
Menstrual CompleteTabletOralKroger2014-03-28Not applicableUs
Menstrual Complete Maximum StrengthTablet, film coatedOralH.E.B.2002-04-29Not applicableUs
Menstrual Midol CompleteTabletOralBayer Inc Consumer Care2006-06-22Not applicableCanada
Menstrual ReliefCapsule, liquid filledOralWalgreen2001-06-14Not applicableUs
Menstrual Relief Extra StrengthTabletOralBetter Living Brands2002-04-29Not applicableUs
Menstrual Relief Maximum StrengthTabletOralTarget Corporation.2014-12-31Not applicableUs
MidolTabletOralNavajo Manuracturing Company2016-09-19Not applicableUs
Midol CompleteTabletOralBayer Health Care Llc, Consumer Care2014-02-10Not applicableUs
Midol Complete GelcapsTablet, coatedOralBayer Health Care Llc, Consumer Care2014-12-15Not applicableUs
Midol Extra Strength GelcapsCapsuleOralBayer Inc Consumer Care1998-06-022004-06-28Canada
Midol Extra Strength MenstrualTabletOralBayer Inc Consumer Care1998-06-022007-08-02Canada
Midol Multi-symptom Caplets Extra StrengthTabletOralSterling Winthrop Inc.1994-12-311996-09-10Canada
Midol Multi-symptom Gelcap Extra StrengthCapsuleOralBayer Inc Consumer Care1995-12-311998-07-30Canada
Midol OneTabletOralBayer Inc Consumer CareNot applicableNot applicableCanada
Midol RegularTabletOralBayer Inc Consumer Care1998-07-062007-08-02Canada
MigergotSuppositoryRectalGw Pharmaceuticals Ltd.1983-10-30Not applicableUs
Migraine FormulaTabletOralSafeway2002-05-07Not applicableUs
Migraine ReliefTablet, film coatedOralWalgreen2002-05-02Not applicableUs
MigrenolTabletOralFour Ventures Enterprises, Inc.2014-11-10Not applicableUs
Nano PpcCreamTopicalYBK Investment, INC2013-11-15Not applicableUs
NervineTabletOralJ L Mathieu Cie Ltee1967-12-311999-08-03Canada
Nervine TabTabletOralJ L Mathieu Cie Ltee1967-12-311999-08-03Canada
NorgesicTablet, multilayerOral3 M Pharmaceuticals1964-03-042015-12-31Us
Norgesic ForteTablet, multilayerOral3 M Pharmaceuticals1964-03-042015-12-31Us
Norgesic Forte TabTabletOral3 M Pharmaceuticals, A Division Of 3 M Canada Company1976-12-312006-07-24Canada
Norgesic TabTabletOral3 M Pharmaceuticals, A Division Of 3 M Canada Company1964-12-312006-07-24Canada
Novo Ac and C 8mg TabTabletOralNovopharm Limited1978-12-312015-10-26Canada
Novo-gesic C15TabletOralNovopharm Limited1986-12-312003-02-10Canada
Novo-gesic C30TabletOralNovopharm Limited1986-12-312003-02-10Canada
Novo-gesic-C8TabletOralNovopharm Limited1985-12-312015-10-26Canada
Novo-propoxyn Compound CapCapsuleOralNovopharm Limited1973-12-312005-08-10Canada
Nu-acetaco #1TabletOralNu Pharm IncNot applicableNot applicableCanada
Oradrine 2 TabTabletOralNutribon (1986) Inc.1995-12-312001-03-30Canada
Oradrine TabletsTabletOralPharmavite Laboratories (1987) Inc.1989-12-312001-03-30Canada
OrbivanCapsuleOralAtley Pharmaceuticals2010-04-23Not applicableUs
Orphenadrine Citrate, Aspirin and CaffeineTablet, multilayerOralRebel Distributors1996-12-31Not applicableUs
Pain AidTabletOralZee Medical Inc1990-12-312012-07-31Canada
Pain Aid EsfTabletOralZee Medical Inc2012-06-12Not applicableUs
Pain Away PlusTablet, film coatedOralMedex Merchandising, Llc2015-10-15Not applicableUs
Pain FreeTabletOralAfassco Inc.2016-10-25Not applicableUs
Pain Free PlusTabletOralAfassco Inc.2016-10-25Not applicableUs
Pain Relief Added StrengthTabletOralBetter Living Brands1992-11-17Not applicableUs
Pain Relief Back and Body Extra StrengthTablet, film coatedOralRite Aid2004-04-12Not applicableUs
Pain Relief Extra StrengthTablet, film coatedOralL&R Distributors, Inc.1992-11-17Not applicableUs
Pain Relief Maximum StrengthTablet, coatedOralSelect Corporation2012-10-15Not applicableUs
Pain Reliever Added StrengthTablet, film coatedOralTarget Corporation.1992-11-172018-05-07Us
Pain Reliever Extra StrengthTablet, film coatedOralCostco Wholesale1992-11-17Not applicableUs
Pain Reliever PlusTablet, film coatedOralClinical Solutions Wholsesale1992-11-17Not applicableUs
Pain Stopper ExtraTabletOralNorth Safety Products2012-03-07Not applicableUs
Pain Stoppers ExtraTablet, coatedOralNorth Safety Products2012-03-07Not applicableUs
Pain Stoppers RegularTabletOralNorth Safety Products2013-04-18Not applicableUs
Painex Tab 0.25grTabletOralIcn Pharmaceuticals1974-12-311998-08-13Canada
Painex Tab 0.5grTabletOralIcn Pharmaceuticals1974-12-311998-08-13Canada
Pamprin Max Menstrual Pain ReliefTabletOralChattem, Inc.2006-02-01Not applicableUs
Panadol ExtraTablet, film coatedOralGlaxo Smith Kline Consumer Healthcare Holdings (Us) Llc2017-03-01Not applicableUs
Physicians Care Extra Strength Pain RelieverTablet, film coatedOralAcme United Corporation2013-09-27Not applicableUs
PMS-pharnal CapsulesCapsuleOralPharmascience IncNot applicableNot applicableCanada
PMS-pharnal TabletsTabletOralPharmascience IncNot applicableNot applicableCanada
PMS-pharnal-C 1/4 CapsulesCapsuleOralPharmascience IncNot applicableNot applicableCanada
PMS-pharnal-C1/2 CapsulesCapsuleOralPharmascience IncNot applicableNot applicableCanada
ProdrinTabletOralGentex Pharma2010-06-01Not applicableUs
Pronal - C1/2 CapsulesCapsuleOralPro Doc Limitee2009-06-252013-01-18Canada
Pronal C1/4 CapsulesCapsuleOralPro Doc Limitee2009-06-252013-01-18Canada
Pronal CapsulesCapsuleOralPro Doc Limitee2009-06-232012-07-23Canada
Pronal TabletsTabletOralPro Doc Limitee2009-06-25Not applicableCanada
Ratio-lenoltec No 1TabletOralTeva1986-12-31Not applicableCanada
Ratio-lenoltec No 2TabletOralTeva1986-12-31Not applicableCanada
Ratio-lenoltec No 3TabletOralTeva1985-12-31Not applicableCanada
Ratio-tecnalTabletOralTeva1984-12-31Not applicableCanada
Ratio-tecnal C 1/2CapsuleOralTeva1984-12-31Not applicableCanada
Ratio-tecnal C 1/4CapsuleOralTeva1984-12-31Not applicableCanada
Regular Strength AspirinTablet, film coatedOralWalgreen2011-01-01Not applicableUs
Rx Act Headache Formula Added StrengthTablet, film coatedOralH.E.B.1992-02-03Not applicableUs
Sed-maxTablet, coatedOralCommand Brands, Llc2014-11-26Not applicableUs
Sedalmex Pain RelieverTabletOralMidway Importing2011-08-15Not applicableUs
Shoprite Migraine FormulaTablet, film coatedOralWakfern Food Corporation2013-06-20Not applicableUs
Signature Care Migraine ReliefTablet, film coatedOralSafeway2015-09-01Not applicableUs
Sinugex 38TabletOralFrega Inc.1988-12-312008-02-13Canada
Smart Sense Migraine FormulaTablet, film coatedOralKmart Corporation2014-04-17Not applicableUs
Smart Sense Migraine ReliefTabletOralKmart Corporation2010-05-27Not applicableUs
Sohmed Pain RelieverTabletOralSOHM Inc.2013-08-25Not applicableUs
StanbackPowderOralMedtech Laboratories, Inc.2012-06-01Not applicableUs
Sunmark Headache ReliefTablet, film coatedOralMc Kesson2003-09-13Not applicableUs
Sunmark Migraine ReliefTabletOralMc Kesson2003-08-18Not applicableUs
Sunmark Tension HeadacheTablet, film coatedOralMc Kesson2008-07-25Not applicableUs
SynalgosCapsuleOralCaraco Pharma, Inc.2008-12-30Not applicableUs
Tamicode TabletsTabletOralViva Pharmaceutical Inc.Not applicableNot applicableCanada
Teen Midol CompleteTabletOralBayer Inc Consumer Care2006-07-29Not applicableCanada
Teen Pms Relief Complete CapletsTabletOralTanta Pharmaceuticals IncNot applicableNot applicableCanada
Tension HeadacheTablet, film coatedOralWalgreen2008-02-05Not applicableUs
Tension Headache Aspirin FreeTabletOralCvs Health2007-01-17Not applicableUs
Tension Headache Aspirin-freeTablet, film coatedOralRite Aid2007-01-17Not applicableUs
Tension Headache ReliefCapsule, gelatin coatedOralTarget Corporation.2009-02-09Not applicableUs
Tension Headache Relief Aspirin FreeTablet, film coatedOralLnk International, Inc.2007-01-17Not applicableUs50844 0428 08 nlmimage10 d738ebe7
Thrulife Extra Strength Headache ReliefTabletOralPolygen Pharmaceuticals Inc.2013-01-31Not applicableUs
Topcare Headache FormulaTablet, film coatedOralTopco Associates1999-01-13Not applicableUs
Topcare Migraine FormulaTabletOralTopco Associates2003-04-01Not applicableUs
TrezixCapsuleOralWraser Pharmaceuticals2009-09-01Not applicableUs
Triaminicin Colds & Flu CapletsTabletOralNovartis1992-12-312000-07-19Canada
Trianal C½CapsuleOralLaboratoire Riva Inc1998-03-09Not applicableCanada
Trianal C¼CapsuleOralLaboratoire Riva Inc2006-12-22Not applicableCanada
Trianal CapsulesCapsuleOralLaboratoire Riva Inc1997-06-02Not applicableCanada
Trianal TabletTabletOralLaboratoire Riva Inc1997-02-07Not applicableCanada
Triatec Fort/strong Ultra Efficace/ultra ReliefTabletOralLaboratoires Trianon IncNot applicableNot applicableCanada
Triatec-8TabletOralLaboratoire Riva Inc1991-12-31Not applicableCanada
Triatec-8 FortTabletOralLaboratoire Riva Inc1992-12-31Not applicableCanada
Tylenol Advanced HeadacheTabletOralMcneil Consumer Healthcare Division Of Johnson & Johnson IncNot applicableNot applicableCanada
Tylenol No 1 TabTabletOralMcneil Pharmaceutical, Division Of Ortho Mcneil Inc.1978-12-311996-09-09Canada
Tylenol No.1 CapletsTabletOralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1971-12-312016-09-29Canada
Tylenol No.1 Forte CapletsTabletOralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1996-08-282015-08-06Canada
Tylenol No1 Forte Tablets With CodeineTabletOralMcneil Pharmaceutical, Division Of Ortho Mcneil Inc.1985-12-311996-09-09Canada
Tylenol Ultra ReliefTabletOralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc2005-01-05Not applicableCanada
Tylenol W Codeine No2 TabTabletOralMcneil Pharmaceutical, Division Of Ortho Mcneil Inc.1978-12-311996-09-09Canada
Tylenol W Codeine No3 TabTabletOralMcneil Pharmaceutical, Division Of Ortho Mcneil Inc.1978-12-311996-09-09Canada
Tylenol With Codeine No. 2 - TabTabletOralJanssen Pharmaceuticals1964-12-31Not applicableCanada
Tylenol With Codeine No. 3 - TabTabletOralJanssen Pharmaceuticals1964-12-31Not applicableCanada
Ultra Headache ReliefTabletOralVita Health Products Inc2005-06-17Not applicableCanada
Up and Up Migraine ReliefTabletOralTarget Corporation.2009-06-12Not applicableUs
Uricalm IntensiveTablet, film coatedOralAlva Amco Pharmacal Companies, Inc.2013-09-23Not applicableUs
VanapainLiquidOralGm Pharmaceuticals2013-07-22Not applicableUs
Vanatol LqSyrupOralGm Pharmaceuticals2015-04-28Not applicableUs
Vanatol SSyrupOralGm Pharmaceuticals2017-07-01Not applicableUs
VanquishTablet, coatedOralMOBERG PHARMA NORTH AMERICA LLC2012-06-26Not applicableUs
Wampole-acetaminophen/codeine/caffeineTabletOralJamp Pharma Corporation2016-12-23Not applicableCanada
ZebutalCapsuleOralShionogi1998-10-282016-10-13Us
Categories
UNII3G6A5W338E
CAS number58-08-2
WeightAverage: 194.1906
Monoisotopic: 194.080375584
Chemical FormulaC8H10N4O2
InChI KeyRYYVLZVUVIJVGH-UHFFFAOYSA-N
InChI
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
IUPAC Name
1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
CN1C=NC2=C1C(=O)N(C)C(=O)N2C
Pharmacology
Indication

For management of fatigue, orthostatic hypotension, and for the short term treatment of apnea of prematurity in infants.

Structured Indications
Pharmacodynamics

Caffeine, a naturally occurring xanthine derivative like theobromine and the bronchodilator theophylline, is used as a CNS stimulant, mild diuretic, and respiratory stimulant (in neonates with apnea of prematurity). Often combined with analgesics or with ergot alkaloids, caffeine is used to treat migraine and other headache types. Over the counter, caffeine is available to treat drowsiness or mild water-weight gain.

Mechanism of action

Caffeine stimulates medullary, vagal, vasomotor, and respiratory centers, promoting bradycardia, vasoconstriction, and increased respiratory rate. This action was previously believed to be due primarily to increased intracellular cyclic 3′,5′-adenosine monophosphate (cyclic AMP) following inhibition of phosphodiesterase, the enzyme that degrades cyclic AMP. It is now thought that xanthines such as caffeine act as antagonists at adenosine-receptors within the plasma membrane of virtually every cell. As adenosine acts as an autocoid, inhibiting the release of neurotransmitters from presynaptic sites but augmenting the actions of norepinephrine or angiotensin, antagonism of adenosine receptors promotes neurotransmitter release. This explains the stimulatory effects of caffeine. Blockade of the adenosine A1 receptor in the heart leads to the accelerated, pronounced "pounding" of the heart upon caffeine intake.

TargetKindPharmacological actionActionsOrganismUniProt ID
Adenosine receptor A1Proteinyes
antagonist
multitarget
HumanP30542 details
Adenosine receptor A2aProteinyes
antagonist
multitarget
HumanP29274 details
cAMP-specific 3',5'-cyclic phosphodiesterase 4BProteinunknown
inhibitor
HumanQ07343 details
Ryanodine receptor 1ProteinunknownNot AvailableHumanP21817 details
Cyclic nucleotide phosphodiesteraseProtein groupunknownNot AvailableHumannot applicabledetails
DNA-dependent protein kinase catalytic subunitProteinunknownNot AvailableHumanP78527 details
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoformProteinunknownNot AvailableHumanO00329 details
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoformProteinunknownNot AvailableHumanP42336 details
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoformProteinunknownNot AvailableHumanP42338 details
Inositol 1,4,5-trisphosphate receptorProtein groupunknownNot AvailableHumannot applicabledetails
Serine-protein kinase ATMProteinunknownNot AvailableHumanQ13315 details
Related Articles
Absorption

Readily absorbed after oral or parenteral administration. The peak plasma level for caffeine range from 6-10mg/L and the mean time to reach peak concentration ranged from 30 minutes to 2 hours.

Volume of distribution
  • 0.8 to 0.9 L/kg [infants]
  • 0.6 L/kg [adults]
Protein binding

Low (25 to 36%).

Metabolism

Hepatic cytochrome P450 1A2 (CYP 1A2) is involved in caffeine biotransformation. About 80% of a dose of caffeine is metabolized to paraxanthine (1,7-dimethylxanthine), 10% to theobromine (3,7-dimethylxanthine), and 4% to theophylline (1,3-dimethylxanthine).

SubstrateEnzymesProduct
Caffeine
TheobromineDetails
Caffeine
TheophyllineDetails
Caffeine
1,3,7-Trimethyluric acidDetails
Caffeine
ParaxanthineDetails
Paraxanthine
1,7-Dimethyluric acidDetails
Theophylline
1-MethylxanthineDetails
1-Methylxanthine
1-Methyluric acidDetails
Paraxanthine
5-Acetylamino-6-formylamino-3-methyluracilDetails
Paraxanthine
Not Available
1-MethylxanthineDetails
Route of elimination

In young infants, the elimination of caffeine is much slower than that in adults due to immature hepatic and/or renal function.

Half life

3 to 7 hours in adults, 65 to 130 hours in neonates

ClearanceNot Available
Toxicity

LD50=127 mg/kg (orally in mice)

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 1A2---(C;C) / (A;C)C allele ADR Directly StudiedMyocardial infarction Details
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Caffeine can be increased when it is combined with Abiraterone.Approved
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Caffeine.Approved
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Caffeine.Approved
AcetaminophenThe serum concentration of Caffeine can be increased when it is combined with Acetaminophen.Approved
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Caffeine.Approved, Vet Approved
AdenosineThe therapeutic efficacy of Adenosine can be decreased when used in combination with Caffeine.Approved, Investigational
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Caffeine.Approved
AgomelatineThe serum concentration of Agomelatine can be increased when it is combined with Caffeine.Approved, Investigational
AlbendazoleThe serum concentration of Caffeine can be increased when it is combined with Albendazole.Approved, Vet Approved
AldosteroneThe serum concentration of Caffeine can be decreased when it is combined with Aldosterone.Experimental
AlectinibThe serum concentration of Caffeine can be increased when it is combined with Alectinib.Approved
AlfentanilThe serum concentration of Caffeine can be increased when it is combined with Alfentanil.Approved, Illicit
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Caffeine.Approved, Investigational
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Caffeine.Approved, Investigational
AlosetronThe metabolism of Alosetron can be decreased when combined with Caffeine.Approved, Withdrawn
AmantadineThe serum concentration of Caffeine can be increased when it is combined with Amantadine.Approved
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Caffeine.Approved, Investigational
Aminohippuric acidThe serum concentration of Caffeine can be increased when it is combined with Aminohippuric acid.Approved
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Caffeine.Approved, Withdrawn
AminophyllineThe metabolism of Aminophylline can be decreased when combined with Caffeine.Approved
AmiodaroneThe metabolism of Caffeine can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Caffeine can be increased when it is combined with Amitriptyline.Approved
AmlodipineThe serum concentration of Caffeine can be increased when it is combined with Amlodipine.Approved
AmprenavirThe serum concentration of Caffeine can be decreased when it is combined with Amprenavir.Approved
AmsacrineThe serum concentration of Caffeine can be increased when it is combined with Amsacrine.Approved
AnagrelideThe metabolism of Anagrelide can be decreased when combined with Caffeine.Approved
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Caffeine.Approved
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Caffeine.Approved
AprepitantThe serum concentration of Caffeine can be increased when it is combined with Aprepitant.Approved, Investigational
Arsenic trioxideThe serum concentration of Arsenic trioxide can be increased when it is combined with Caffeine.Approved, Investigational
ArtemetherThe metabolism of Caffeine can be decreased when combined with Artemether.Approved
AsenapineThe metabolism of Asenapine can be decreased when combined with Caffeine.Approved
AstemizoleThe serum concentration of Caffeine can be increased when it is combined with Astemizole.Approved, Withdrawn
AtazanavirThe metabolism of Caffeine can be decreased when combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Caffeine can be increased when it is combined with Atenolol.Approved
AtomoxetineThe metabolism of Caffeine can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe serum concentration of Caffeine can be increased when it is combined with Atorvastatin.Approved
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Caffeine.Approved, Investigational
AzelastineThe serum concentration of Caffeine can be increased when it is combined with Azelastine.Approved
AzithromycinThe serum concentration of Caffeine can be increased when it is combined with Azithromycin.Approved
BendamustineThe metabolism of Bendamustine can be decreased when combined with Caffeine.Approved, Investigational
BenzocaineThe serum concentration of Caffeine can be increased when it is combined with Benzocaine.Approved
Benzyl alcoholThe metabolism of Benzyl alcohol can be decreased when combined with Caffeine.Approved
BepridilThe serum concentration of Caffeine can be increased when it is combined with Bepridil.Approved, Withdrawn
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Caffeine.Approved, Vet Approved
BetaxololThe metabolism of Betaxolol can be decreased when combined with Caffeine.Approved
BexaroteneThe serum concentration of Caffeine can be decreased when it is combined with Bexarotene.Approved, Investigational
BiperidenThe serum concentration of Caffeine can be increased when it is combined with Biperiden.Approved
BoceprevirThe metabolism of Caffeine can be decreased when combined with Boceprevir.Withdrawn
BortezomibThe metabolism of Caffeine can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Caffeine can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Caffeine.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Caffeine.Approved
BromazepamThe metabolism of Bromazepam can be decreased when combined with Caffeine.Approved, Illicit
BromocriptineThe serum concentration of Caffeine can be increased when it is combined with Bromocriptine.Approved, Investigational
BupivacaineThe metabolism of Bupivacaine can be decreased when combined with Caffeine.Approved, Investigational
BuprenorphineThe serum concentration of Caffeine can be increased when it is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BupropionThe metabolism of Caffeine can be decreased when combined with Bupropion.Approved
BuspironeThe serum concentration of Caffeine can be increased when it is combined with Buspirone.Approved, Investigational
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Caffeine.Approved
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Caffeine.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Caffeine.Approved
CandesartanThe serum concentration of Caffeine can be increased when it is combined with Candesartan.Approved
CapecitabineThe metabolism of Caffeine can be decreased when combined with Capecitabine.Approved, Investigational
CaptoprilThe serum concentration of Caffeine can be increased when it is combined with Captopril.Approved
CarbamazepineThe metabolism of Caffeine can be increased when combined with Carbamazepine.Approved, Investigational
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Caffeine.Approved
CarmustineThe metabolism of Carmustine can be decreased when combined with Caffeine.Approved
CarvedilolThe serum concentration of Caffeine can be increased when it is combined with Carvedilol.Approved, Investigational
CaspofunginThe serum concentration of Caffeine can be increased when it is combined with Caspofungin.Approved
CelecoxibThe metabolism of Caffeine can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Caffeine can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Caffeine.Withdrawn
ChloroquineThe serum concentration of Caffeine can be increased when it is combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Caffeine can be increased when it is combined with Chlorpromazine.Approved, Vet Approved
ChlorpropamideThe serum concentration of Caffeine can be increased when it is combined with Chlorpropamide.Approved
ChlorprothixeneThe serum concentration of Caffeine can be increased when it is combined with Chlorprothixene.Approved, Withdrawn
ChlorzoxazoneThe metabolism of Chlorzoxazone can be decreased when combined with Caffeine.Approved
CholecalciferolThe metabolism of Caffeine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CholesterolThe serum concentration of Caffeine can be increased when it is combined with Cholesterol.Experimental
Cholic AcidThe serum concentration of Caffeine can be decreased when it is combined with Cholic Acid.Approved
CilazaprilThe serum concentration of Caffeine can be increased when it is combined with Cilazapril.Approved
CilostazolThe metabolism of Cilostazol can be decreased when combined with Caffeine.Approved
CimetidineThe serum concentration of Caffeine can be decreased when it is combined with Cimetidine.Approved
CinacalcetThe metabolism of Caffeine can be decreased when combined with Cinacalcet.Approved
CinnarizineThe metabolism of Cinnarizine can be decreased when combined with Caffeine.Approved
CiprofloxacinThe serum concentration of Caffeine can be increased when it is combined with Ciprofloxacin.Approved, Investigational
CisaprideThe metabolism of Cisapride can be decreased when combined with Caffeine.Approved, Investigational, Withdrawn
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Caffeine.Approved
CitalopramThe serum concentration of Caffeine can be increased when it is combined with Citalopram.Approved
ClarithromycinThe metabolism of Caffeine can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Caffeine can be decreased when combined with Clemastine.Approved
ClenbuterolThe metabolism of Clenbuterol can be decreased when combined with Caffeine.Approved, Vet Approved
ClevidipineThe metabolism of Clevidipine can be decreased when combined with Caffeine.Approved
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Caffeine.Approved, Illicit
ClofazimineThe serum concentration of Caffeine can be increased when it is combined with Clofazimine.Approved, Investigational
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Caffeine.Approved, Investigational
ClomipramineThe serum concentration of Caffeine can be increased when it is combined with Clomipramine.Approved, Vet Approved
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Caffeine.Approved
ClopidogrelThe metabolism of Caffeine can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe metabolism of Caffeine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe serum concentration of Clozapine can be increased when it is combined with Caffeine.Approved
CobicistatThe serum concentration of Caffeine can be increased when it is combined with Cobicistat.Approved
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Caffeine.Approved
CocaineThe metabolism of Caffeine can be decreased when combined with Cocaine.Approved, Illicit
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Caffeine.Approved
ColforsinThe serum concentration of Caffeine can be increased when it is combined with Colforsin.Experimental
ConivaptanThe serum concentration of Caffeine can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated estrogensThe serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Caffeine.Approved
CrizotinibThe metabolism of Caffeine can be decreased when combined with Crizotinib.Approved
CyclobenzaprineThe metabolism of Cyclobenzaprine can be decreased when combined with Caffeine.Approved
CyclophosphamideThe serum concentration of Caffeine can be increased when it is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe metabolism of Caffeine can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Caffeine can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Caffeine.Approved
DabrafenibThe serum concentration of Caffeine can be decreased when it is combined with Dabrafenib.Approved
DacarbazineThe metabolism of Dacarbazine can be decreased when combined with Caffeine.Approved, Investigational
DaclatasvirThe serum concentration of Caffeine can be increased when it is combined with Daclatasvir.Approved
DactinomycinThe serum concentration of Caffeine can be increased when it is combined with Dactinomycin.Approved
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Caffeine.Approved
DarifenacinThe metabolism of Caffeine can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Caffeine can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Caffeine can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Caffeine can be decreased when it is combined with Daunorubicin.Approved
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Caffeine.Approved
DeferasiroxThe serum concentration of Caffeine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Caffeine can be decreased when combined with Delavirdine.Approved
DesipramineThe serum concentration of Caffeine can be increased when it is combined with Desipramine.Approved
DesloratadineThe serum concentration of Caffeine can be increased when it is combined with Desloratadine.Approved, Investigational
DexamethasoneThe serum concentration of Caffeine can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DexfenfluramineThe metabolism of Dexfenfluramine can be decreased when combined with Caffeine.Approved, Illicit, Withdrawn
DextromethorphanThe serum concentration of Caffeine can be increased when it is combined with Dextromethorphan.Approved
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Caffeine.Approved, Illicit, Vet Approved
DiclofenacThe serum concentration of Caffeine can be increased when it is combined with Diclofenac.Approved, Vet Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Caffeine.Approved
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Caffeine.Approved
DigoxinThe serum concentration of Caffeine can be decreased when it is combined with Digoxin.Approved
DihydroergotamineThe metabolism of Caffeine can be decreased when combined with Dihydroergotamine.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Caffeine.Illicit
DiltiazemThe metabolism of Caffeine can be decreased when combined with Diltiazem.Approved
DinoprostoneThe metabolism of Dinoprostone can be decreased when combined with Caffeine.Approved
DiphenhydramineThe metabolism of Diphenhydramine can be decreased when combined with Caffeine.Approved
DipyridamoleThe serum concentration of Caffeine can be increased when it is combined with Dipyridamole.Approved
DisulfiramThe metabolism of Caffeine can be decreased when combined with Disulfiram.Approved
DocetaxelThe serum concentration of Docetaxel can be increased when it is combined with Caffeine.Approved, Investigational
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Caffeine.Approved, Investigational, Vet Approved
DoxazosinThe serum concentration of Caffeine can be increased when it is combined with Doxazosin.Approved
DoxepinThe serum concentration of Caffeine can be increased when it is combined with Doxepin.Approved
DoxofyllineThe risk or severity of adverse effects can be increased when Caffeine is combined with Doxofylline.Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Caffeine.Approved, Investigational
DoxorubicinThe serum concentration of Caffeine can be decreased when it is combined with Doxorubicin.Approved, Investigational
DoxycyclineThe metabolism of Caffeine can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronabinolThe serum concentration of Caffeine can be increased when it is combined with Dronabinol.Approved, Illicit
DronedaroneThe metabolism of Caffeine can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Duloxetine can be decreased when combined with Caffeine.Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Caffeine.Approved
EfavirenzThe serum concentration of Caffeine can be decreased when it is combined with Efavirenz.Approved, Investigational
ElbasvirThe serum concentration of Caffeine can be increased when it is combined with Elbasvir.Approved
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Caffeine.Approved, Investigational
EliglustatThe metabolism of Caffeine can be decreased when combined with Eliglustat.Approved
EltrombopagThe metabolism of Eltrombopag can be decreased when combined with Caffeine.Approved
EnalaprilThe serum concentration of Caffeine can be increased when it is combined with Enalapril.Approved, Vet Approved
EnzalutamideThe serum concentration of Caffeine can be decreased when it is combined with Enzalutamide.Approved
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Caffeine.Approved, Investigational
ErgonovineThe serum concentration of Caffeine can be increased when it is combined with Ergonovine.Approved
ErgotamineThe serum concentration of Caffeine can be increased when it is combined with Ergotamine.Approved
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Caffeine.Approved, Investigational
ErythromycinThe metabolism of Caffeine can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Caffeine can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Caffeine.Approved, Investigational, Vet Approved
EstramustineThe serum concentration of Caffeine can be increased when it is combined with Estramustine.Approved
EstriolThe serum concentration of Caffeine can be decreased when it is combined with Estriol.Approved, Vet Approved
EstroneThe serum concentration of Caffeine can be decreased when it is combined with Estrone.Approved
Estrone sulfateThe metabolism of Estrone sulfate can be decreased when combined with Caffeine.Approved
EthanolThe metabolism of Ethanol can be decreased when combined with Caffeine.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Caffeine.Approved
EtoposideThe serum concentration of Caffeine can be increased when it is combined with Etoposide.Approved
EtoricoxibThe metabolism of Etoricoxib can be decreased when combined with Caffeine.Approved, Investigational
EtravirineThe serum concentration of Caffeine can be decreased when it is combined with Etravirine.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Caffeine.Approved
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Caffeine.Approved
FelodipineThe serum concentration of Caffeine can be increased when it is combined with Felodipine.Approved, Investigational
FentanylThe serum concentration of Caffeine can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Caffeine.Approved
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Caffeine.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Caffeine.Approved
FloxuridineThe metabolism of Caffeine can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Caffeine can be decreased when combined with Fluconazole.Approved
FlunarizineThe metabolism of Flunarizine can be decreased when combined with Caffeine.Approved
FlunitrazepamThe metabolism of Flunitrazepam can be decreased when combined with Caffeine.Approved, Illicit
FluorouracilThe metabolism of Caffeine can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Caffeine can be decreased when combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe serum concentration of Caffeine can be increased when it is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe serum concentration of Caffeine can be increased when it is combined with Fluphenazine.Approved
FlurazepamThe serum concentration of Caffeine can be increased when it is combined with Flurazepam.Approved, Illicit
FlutamideThe metabolism of Flutamide can be decreased when combined with Caffeine.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Caffeine.Approved
FluvastatinThe metabolism of Caffeine can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Caffeine can be decreased when combined with Fluvoxamine.Approved, Investigational
FormoterolThe risk or severity of adverse effects can be increased when Caffeine is combined with Formoterol.Approved, Investigational
FosamprenavirThe metabolism of Caffeine can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Caffeine can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Caffeine can be increased when combined with Fosphenytoin.Approved
FrovatriptanThe metabolism of Frovatriptan can be decreased when combined with Caffeine.Approved, Investigational
Fusidic AcidThe serum concentration of Caffeine can be increased when it is combined with Fusidic Acid.Approved
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Caffeine.Approved, Investigational
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Caffeine.Approved
GemfibrozilThe metabolism of Caffeine can be decreased when combined with Gemfibrozil.Approved
GenisteinThe serum concentration of Caffeine can be increased when it is combined with Genistein.Investigational
GlyburideThe serum concentration of Caffeine can be increased when it is combined with Glyburide.Approved
Gramicidin DThe serum concentration of Caffeine can be increased when it is combined with Gramicidin D.Approved
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Caffeine.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Caffeine.Withdrawn
GuanabenzThe metabolism of Guanabenz can be decreased when combined with Caffeine.Approved
HaloperidolThe serum concentration of Caffeine can be increased when it is combined with Haloperidol.Approved
HesperetinThe metabolism of Hesperetin can be decreased when combined with Caffeine.Approved
HexobarbitalThe metabolism of Hexobarbital can be decreased when combined with Caffeine.Approved
HydrocortisoneThe serum concentration of Caffeine can be increased when it is combined with Hydrocortisone.Approved, Vet Approved
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Caffeine.Approved
IdelalisibThe serum concentration of Caffeine can be increased when it is combined with Idelalisib.Approved
IloperidoneThe metabolism of Iloperidone can be decreased when combined with Caffeine.Approved
ImatinibThe metabolism of Caffeine can be decreased when combined with Imatinib.Approved
ImipramineThe serum concentration of Caffeine can be increased when it is combined with Imipramine.Approved
ImiquimodThe metabolism of Imiquimod can be decreased when combined with Caffeine.Approved, Investigational
IndacaterolThe risk or severity of adverse effects can be increased when Caffeine is combined with Indacaterol.Approved
IndinavirThe metabolism of Caffeine can be decreased when combined with Indinavir.Approved
IndomethacinThe serum concentration of Caffeine can be increased when it is combined with Indomethacin.Approved, Investigational
IrbesartanThe metabolism of Caffeine can be decreased when combined with Irbesartan.Approved, Investigational
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Caffeine.Approved, Investigational
IsavuconazoniumThe metabolism of Caffeine can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Caffeine can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Caffeine can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Caffeine can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Caffeine can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Caffeine can be increased when it is combined with Ivermectin.Approved, Vet Approved
IxazomibThe metabolism of Ixazomib can be decreased when combined with Caffeine.Approved
KetamineThe serum concentration of Caffeine can be increased when it is combined with Ketamine.Approved, Vet Approved
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Caffeine.Approved
KetoconazoleThe metabolism of Caffeine can be decreased when combined with Ketoconazole.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Caffeine.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Caffeine.Approved, Investigational
LansoprazoleThe serum concentration of Caffeine can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe serum concentration of Caffeine can be increased when it is combined with Lapatinib.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Caffeine.Approved
LeflunomideThe metabolism of Leflunomide can be decreased when combined with Caffeine.Approved, Investigational
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Caffeine.Approved
LenvatinibThe serum concentration of Lenvatinib can be increased when it is combined with Caffeine.Approved
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Caffeine.Approved, Investigational
LevobupivacaineThe metabolism of Levobupivacaine can be decreased when combined with Caffeine.Approved
LevofloxacinThe serum concentration of Caffeine can be increased when it is combined with Levofloxacin.Approved, Investigational
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Caffeine.Approved
LevothyroxineThe serum concentration of Caffeine can be decreased when it is combined with Levothyroxine.Approved
LidocaineThe serum concentration of Caffeine can be increased when it is combined with Lidocaine.Approved, Vet Approved
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Caffeine.Approved
LiothyronineThe serum concentration of Caffeine can be decreased when it is combined with Liothyronine.Approved, Vet Approved
LiotrixThe serum concentration of Caffeine can be decreased when it is combined with Liotrix.Approved
LisinoprilThe serum concentration of Caffeine can be increased when it is combined with Lisinopril.Approved, Investigational
LithiumThe serum concentration of Lithium can be decreased when it is combined with Caffeine.Approved
LomefloxacinThe metabolism of Lomefloxacin can be decreased when combined with Caffeine.Approved
LomitapideThe serum concentration of Caffeine can be increased when it is combined with Lomitapide.Approved
LoperamideThe serum concentration of Caffeine can be increased when it is combined with Loperamide.Approved
LopinavirThe metabolism of Caffeine can be decreased when combined with Lopinavir.Approved
LoratadineThe serum concentration of Caffeine can be increased when it is combined with Loratadine.Approved
LorcaserinThe metabolism of Lorcaserin can be decreased when combined with Caffeine.Approved
LosartanThe serum concentration of Caffeine can be increased when it is combined with Losartan.Approved
LovastatinThe metabolism of Caffeine can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Caffeine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Caffeine can be increased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Caffeine can be decreased when combined with Lumefantrine.Approved
LumiracoxibThe metabolism of Lumiracoxib can be decreased when combined with Caffeine.Approved, Investigational
MalathionThe metabolism of Malathion can be decreased when combined with Caffeine.Approved, Investigational
MannitolThe serum concentration of Mannitol can be increased when it is combined with Caffeine.Approved, Investigational
MaprotilineThe serum concentration of Caffeine can be increased when it is combined with Maprotiline.Approved
MebendazoleThe serum concentration of Caffeine can be increased when it is combined with Mebendazole.Approved, Vet Approved
MefloquineThe serum concentration of Caffeine can be increased when it is combined with Mefloquine.Approved
Megestrol acetateThe serum concentration of Caffeine can be increased when it is combined with Megestrol acetate.Approved, Vet Approved
MelatoninThe metabolism of Melatonin can be decreased when combined with Caffeine.Approved, Nutraceutical, Vet Approved
MenadioneThe metabolism of Menadione can be decreased when combined with Caffeine.Approved, Nutraceutical
MephenytoinThe metabolism of Mephenytoin can be decreased when combined with Caffeine.Investigational, Withdrawn
MeprobamateThe serum concentration of Caffeine can be increased when it is combined with Meprobamate.Approved, Illicit
MethadoneThe serum concentration of Caffeine can be increased when it is combined with Methadone.Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Caffeine.Approved
MethotrimeprazineThe metabolism of Caffeine can be decreased when combined with Methotrimeprazine.Approved
MethoxyfluraneThe metabolism of Methoxyflurane can be decreased when combined with Caffeine.Approved, Vet Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Caffeine.Approved, Vet Approved
MetoprololThe serum concentration of Caffeine can be increased when it is combined with Metoprolol.Approved, Investigational
MexiletineThe metabolism of Caffeine can be decreased when combined with Mexiletine.Approved
MianserinThe metabolism of Mianserin can be decreased when combined with Caffeine.Approved
MibefradilThe serum concentration of Caffeine can be increased when it is combined with Mibefradil.Withdrawn
MiconazoleThe serum concentration of Caffeine can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe serum concentration of Caffeine can be decreased when it is combined with Midazolam.Approved, Illicit
MifepristoneThe serum concentration of Caffeine can be increased when it is combined with Mifepristone.Approved, Investigational
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Caffeine.Approved
MirtazapineThe metabolism of Mirtazapine can be decreased when combined with Caffeine.Approved
MitomycinThe serum concentration of Caffeine can be increased when it is combined with Mitomycin.Approved
MitotaneThe serum concentration of Caffeine can be decreased when it is combined with Mitotane.Approved
MitoxantroneThe serum concentration of Caffeine can be decreased when it is combined with Mitoxantrone.Approved, Investigational
ModafinilThe serum concentration of Caffeine can be decreased when it is combined with Modafinil.Approved, Investigational
MorphineThe serum concentration of Caffeine can be increased when it is combined with Morphine.Approved, Investigational
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Caffeine.Approved, Investigational
NabumetoneThe metabolism of Nabumetone can be decreased when combined with Caffeine.Approved
NadololThe serum concentration of Nadolol can be increased when it is combined with Caffeine.Approved
NafcillinThe serum concentration of Caffeine can be decreased when it is combined with Nafcillin.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Caffeine.Approved
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Caffeine.Approved, Vet Approved
NaltrexoneThe serum concentration of Caffeine can be increased when it is combined with Naltrexone.Approved, Investigational, Vet Approved
NaproxenThe metabolism of Naproxen can be decreased when combined with Caffeine.Approved, Vet Approved
NaringeninThe serum concentration of Caffeine can be increased when it is combined with Naringenin.Experimental
NefazodoneThe metabolism of Caffeine can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Caffeine can be decreased when combined with Nelfinavir.Approved
NeostigmineThe serum concentration of Caffeine can be increased when it is combined with Neostigmine.Approved, Vet Approved
NetupitantThe serum concentration of Caffeine can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Caffeine can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Caffeine can be decreased when combined with Nicardipine.Approved
NicotineThe metabolism of Nicotine can be decreased when combined with Caffeine.Approved
NifedipineThe serum concentration of Caffeine can be decreased when it is combined with Nifedipine.Approved
NilotinibThe metabolism of Caffeine can be decreased when combined with Nilotinib.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Caffeine.Approved
NisoldipineThe serum concentration of Caffeine can be increased when it is combined with Nisoldipine.Approved
NitrazepamThe serum concentration of Caffeine can be increased when it is combined with Nitrazepam.Approved
NitrendipineThe serum concentration of Caffeine can be increased when it is combined with Nitrendipine.Approved
Nitric OxideThe metabolism of Nitric Oxide can be decreased when combined with Caffeine.Approved
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Caffeine.Approved
NorethisteroneThe serum concentration of Caffeine can be decreased when it is combined with Norethisterone.Approved
NorfloxacinThe serum concentration of Caffeine can be increased when it is combined with Norfloxacin.Approved
NortriptylineThe metabolism of Nortriptyline can be decreased when combined with Caffeine.Approved
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Caffeine.Approved, Investigational
OlaparibThe metabolism of Caffeine can be decreased when combined with Olaparib.Approved
OlodaterolThe risk or severity of adverse effects can be increased when Caffeine is combined with Olodaterol.Approved
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Caffeine.Approved
OmeprazoleThe serum concentration of Caffeine can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OndansetronThe metabolism of Ondansetron can be decreased when combined with Caffeine.Approved
OsimertinibThe serum concentration of Caffeine can be increased when it is combined with Osimertinib.Approved
OxaliplatinThe metabolism of Oxaliplatin can be decreased when combined with Caffeine.Approved, Investigational
OxtriphyllineThe metabolism of Oxtriphylline can be decreased when combined with Caffeine.Approved
P-NitrophenolThe serum concentration of Caffeine can be increased when it is combined with P-Nitrophenol.Experimental
PaclitaxelThe serum concentration of Caffeine can be increased when it is combined with Paclitaxel.Approved, Vet Approved
PalbociclibThe serum concentration of Caffeine can be increased when it is combined with Palbociclib.Approved
Palmitic AcidThe serum concentration of Caffeine can be increased when it is combined with Palmitic Acid.Experimental
PalonosetronThe metabolism of Palonosetron can be decreased when combined with Caffeine.Approved, Investigational
PanobinostatThe serum concentration of Caffeine can be increased when it is combined with Panobinostat.Approved, Investigational
PantoprazoleThe serum concentration of Caffeine can be increased when it is combined with Pantoprazole.Approved
ParoxetineThe metabolism of Caffeine can be decreased when combined with Paroxetine.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Caffeine.Approved
Peginterferon alfa-2bThe serum concentration of Caffeine can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentamidineThe metabolism of Pentamidine can be decreased when combined with Caffeine.Approved
PentobarbitalThe metabolism of Caffeine can be increased when combined with Pentobarbital.Approved, Vet Approved
PentoxifyllineThe metabolism of Pentoxifylline can be decreased when combined with Caffeine.Approved, Investigational
PerindoprilThe serum concentration of Caffeine can be increased when it is combined with Perindopril.Approved
PerphenazineThe metabolism of Perphenazine can be decreased when combined with Caffeine.Approved
PhenacetinThe metabolism of Phenacetin can be decreased when combined with Caffeine.Withdrawn
PhenobarbitalThe metabolism of Caffeine can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Caffeine can be increased when combined with Phenytoin.Approved, Vet Approved
PimozideThe serum concentration of Caffeine can be increased when it is combined with Pimozide.Approved
PioglitazoneThe metabolism of Caffeine can be decreased when combined with Pioglitazone.Approved, Investigational
PipotiazineThe metabolism of Pipotiazine can be decreased when combined with Caffeine.Approved
PirfenidoneThe serum concentration of Pirfenidone can be increased when it is combined with Caffeine.Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Caffeine.Approved
Platelet Activating FactorThe serum concentration of Caffeine can be decreased when it is combined with Platelet Activating Factor.Experimental
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Caffeine.Approved
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Caffeine.Approved
PosaconazoleThe metabolism of Caffeine can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Caffeine.Approved
PraziquantelThe metabolism of Praziquantel can be decreased when combined with Caffeine.Approved, Vet Approved
PrazosinThe serum concentration of Caffeine can be increased when it is combined with Prazosin.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Caffeine.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Caffeine.Approved, Vet Approved
PrimaquineThe metabolism of Primaquine can be decreased when combined with Caffeine.Approved
PrimidoneThe metabolism of Caffeine can be increased when combined with Primidone.Approved, Vet Approved
ProbenecidThe serum concentration of Caffeine can be increased when it is combined with Probenecid.Approved
ProgesteroneThe serum concentration of Caffeine can be decreased when it is combined with Progesterone.Approved, Vet Approved
ProguanilThe metabolism of Proguanil can be decreased when combined with Caffeine.Approved
PromazineThe metabolism of Promazine can be decreased when combined with Caffeine.Approved, Vet Approved
PromethazineThe serum concentration of Caffeine can be increased when it is combined with Promethazine.Approved
PropafenoneThe serum concentration of Caffeine can be increased when it is combined with Propafenone.Approved
PropofolThe metabolism of Propofol can be decreased when combined with Caffeine.Approved, Investigational, Vet Approved
PropranololThe serum concentration of Propranolol can be increased when it is combined with Caffeine.Approved, Investigational
ProtriptylineThe serum concentration of Caffeine can be increased when it is combined with Protriptyline.Approved
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Caffeine.Approved
PyrazinamideThe metabolism of Pyrazinamide can be decreased when combined with Caffeine.Approved
PyrimethamineThe metabolism of Caffeine can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuercetinThe serum concentration of Caffeine can be increased when it is combined with Quercetin.Experimental
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Caffeine.Approved
QuinacrineThe serum concentration of Caffeine can be increased when it is combined with Quinacrine.Approved
QuinidineThe metabolism of Caffeine can be decreased when combined with Quinidine.Approved
QuinineThe serum concentration of Caffeine can be increased when it is combined with Quinine.Approved
RabeprazoleThe metabolism of Caffeine can be decreased when combined with Rabeprazole.Approved, Investigational
RamelteonThe metabolism of Ramelteon can be decreased when combined with Caffeine.Approved, Investigational
RanitidineThe serum concentration of Caffeine can be increased when it is combined with Ranitidine.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Caffeine.Approved, Investigational
RasagilineThe metabolism of Rasagiline can be decreased when combined with Caffeine.Approved
ReboxetineThe serum concentration of Caffeine can be increased when it is combined with Reboxetine.Approved, Investigational
RegadenosonCaffeine may decrease the vasodilatory activities of Regadenoson.Approved
RegorafenibThe serum concentration of Caffeine can be increased when it is combined with Regorafenib.Approved
ReserpineThe serum concentration of Caffeine can be decreased when it is combined with Reserpine.Approved
ResveratrolThe metabolism of Resveratrol can be decreased when combined with Caffeine.Experimental, Investigational
RifabutinThe metabolism of Caffeine can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Caffeine can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Caffeine can be increased when combined with Rifapentine.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Caffeine.Approved, Investigational
RilpivirineThe serum concentration of Caffeine can be increased when it is combined with Rilpivirine.Approved
RiluzoleThe metabolism of Riluzole can be decreased when combined with Caffeine.Approved, Investigational
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Caffeine.Approved, Investigational
RitonavirThe metabolism of Caffeine can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Caffeine.Approved
RizatriptanThe metabolism of Rizatriptan can be decreased when combined with Caffeine.Approved
RofecoxibThe metabolism of Rofecoxib can be decreased when combined with Caffeine.Investigational, Withdrawn
RolapitantThe serum concentration of Caffeine can be increased when it is combined with Rolapitant.Approved
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Caffeine.Approved, Investigational
RopiniroleThe metabolism of Ropinirole can be decreased when combined with Caffeine.Approved, Investigational
RopivacaineThe metabolism of Ropivacaine can be decreased when combined with Caffeine.Approved
RosiglitazoneThe metabolism of Caffeine can be decreased when combined with Rosiglitazone.Approved, Investigational
RotigotineThe metabolism of Rotigotine can be decreased when combined with Caffeine.Approved
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Caffeine.Approved, Vet Approved
SaquinavirThe metabolism of Caffeine can be decreased when combined with Saquinavir.Approved, Investigational
ScopolamineThe serum concentration of Caffeine can be increased when it is combined with Scopolamine.Approved
SecobarbitalThe metabolism of Caffeine can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineThe serum concentration of Caffeine can be increased when it is combined with Selegiline.Approved, Investigational, Vet Approved
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Caffeine.Approved
SertralineThe serum concentration of Caffeine can be increased when it is combined with Sertraline.Approved
SildenafilThe metabolism of Caffeine can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Caffeine.Approved
SiltuximabThe serum concentration of Caffeine can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Caffeine can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Caffeine can be increased when it is combined with Simvastatin.Approved
SirolimusThe serum concentration of Caffeine can be decreased when it is combined with Sirolimus.Approved, Investigational
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Caffeine.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Caffeine.Approved
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Caffeine.Approved, Investigational
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Caffeine.Approved
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Caffeine.Experimental
SpironolactoneThe serum concentration of Caffeine can be increased when it is combined with Spironolactone.Approved
St. John's WortThe serum concentration of Caffeine can be decreased when it is combined with St. John's Wort.Nutraceutical
StaurosporineThe serum concentration of Caffeine can be increased when it is combined with Staurosporine.Experimental
StiripentolThe serum concentration of Caffeine can be increased when it is combined with Stiripentol.Approved
StreptozocinThe serum concentration of Caffeine can be decreased when it is combined with Streptozocin.Approved
SulfadiazineThe metabolism of Caffeine can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Caffeine can be decreased when combined with Sulfamethoxazole.Approved
SulfinpyrazoneThe serum concentration of Caffeine can be increased when it is combined with Sulfinpyrazone.Approved
SulfisoxazoleThe metabolism of Caffeine can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SumatriptanThe serum concentration of Caffeine can be increased when it is combined with Sumatriptan.Approved, Investigational
SunitinibThe serum concentration of Caffeine can be increased when it is combined with Sunitinib.Approved, Investigational
TacrineThe serum concentration of Caffeine can be increased when it is combined with Tacrine.Withdrawn
TacrolimusThe serum concentration of Caffeine can be decreased when it is combined with Tacrolimus.Approved, Investigational
TamoxifenThe serum concentration of Caffeine can be decreased when it is combined with Tamoxifen.Approved
Taurocholic AcidThe serum concentration of Caffeine can be increased when it is combined with Taurocholic Acid.Experimental
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Caffeine.Approved
TelaprevirThe metabolism of Caffeine can be decreased when combined with Telaprevir.Withdrawn
TelithromycinThe metabolism of Caffeine can be decreased when combined with Telithromycin.Approved
TelmisartanThe serum concentration of Caffeine can be increased when it is combined with Telmisartan.Approved, Investigational
TemafloxacinThe metabolism of Temafloxacin can be decreased when combined with Caffeine.Withdrawn
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Caffeine.Approved
Tenofovir disoproxilThe metabolism of Caffeine can be decreased when combined with Tenofovir.Approved, Investigational
TerazosinThe serum concentration of Caffeine can be increased when it is combined with Terazosin.Approved
TerbinafineThe metabolism of Caffeine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TerfenadineThe serum concentration of Caffeine can be increased when it is combined with Terfenadine.Withdrawn
TeriflunomideThe serum concentration of Caffeine can be decreased when it is combined with Teriflunomide.Approved
TesmilifeneThe serum concentration of Caffeine can be decreased when it is combined with Tesmilifene.Investigational
TestosteroneThe serum concentration of Caffeine can be increased when it is combined with Testosterone.Approved, Investigational
ThalidomideThe metabolism of Thalidomide can be decreased when combined with Caffeine.Approved, Investigational, Withdrawn
TheobromineThe metabolism of Theobromine can be decreased when combined with Caffeine.Approved
TheophyllineThe metabolism of Theophylline can be decreased when combined with Caffeine.Approved
ThiabendazoleThe metabolism of Thiabendazole can be decreased when combined with Caffeine.Approved, Vet Approved
ThioridazineThe metabolism of Caffeine can be decreased when combined with Thioridazine.Withdrawn
ThiothixeneThe metabolism of Thiothixene can be decreased when combined with Caffeine.Approved
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Caffeine.Approved
TiclopidineThe metabolism of Caffeine can be decreased when combined with Ticlopidine.Approved
TimololThe serum concentration of Timolol can be increased when it is combined with Caffeine.Approved
TipranavirThe metabolism of Caffeine can be decreased when combined with Tipranavir.Approved, Investigational
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Caffeine.Approved
TocilizumabThe serum concentration of Caffeine can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Caffeine can be decreased when combined with Tolbutamide.Approved
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Caffeine.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Caffeine.Approved, Investigational
ToremifeneThe serum concentration of Toremifene can be increased when it is combined with Caffeine.Approved, Investigational
TranylcypromineThe metabolism of Caffeine can be decreased when combined with Tranylcypromine.Approved
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Caffeine.Approved
TrazodoneThe serum concentration of Caffeine can be decreased when it is combined with Trazodone.Approved, Investigational
TriamtereneThe metabolism of Triamterene can be decreased when combined with Caffeine.Approved
TrifluoperazineThe serum concentration of Caffeine can be increased when it is combined with Trifluoperazine.Approved
TriflupromazineThe serum concentration of Caffeine can be increased when it is combined with Triflupromazine.Approved, Vet Approved
TrimethoprimThe serum concentration of Caffeine can be decreased when it is combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe serum concentration of Caffeine can be increased when it is combined with Trimipramine.Approved
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Caffeine.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Caffeine.Approved
VadimezanThe metabolism of ASA404 can be decreased when combined with Caffeine.Investigational
Valproic AcidThe metabolism of Caffeine can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Caffeine can be decreased when combined with Valsartan.Approved, Investigational
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Caffeine.Approved
VemurafenibThe serum concentration of Caffeine can be increased when it is combined with Vemurafenib.Approved
VenetoclaxThe serum concentration of Venetoclax can be increased when it is combined with Caffeine.Approved
VenlafaxineThe metabolism of Caffeine can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Caffeine can be decreased when combined with Verapamil.Approved
VinblastineThe serum concentration of Caffeine can be decreased when it is combined with Vinblastine.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Caffeine.Approved, Investigational
VincristineThe serum concentration of Caffeine can be decreased when it is combined with Vincristine.Approved, Investigational
VinorelbineThe serum concentration of Caffeine can be increased when it is combined with Vinorelbine.Approved, Investigational
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Caffeine.Approved
VoriconazoleThe metabolism of Caffeine can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinThe metabolism of Warfarin can be decreased when combined with Caffeine.Approved
ZafirlukastThe metabolism of Caffeine can be decreased when combined with Zafirlukast.Approved, Investigational
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Caffeine.Approved
ZileutonThe metabolism of Zileuton can be decreased when combined with Caffeine.Approved, Investigational, Withdrawn
ZimelidineThe serum concentration of Caffeine can be increased when it is combined with Zimelidine.Withdrawn
ZiprasidoneThe metabolism of Caffeine can be decreased when combined with Ziprasidone.Approved
ZolmitriptanThe metabolism of Zolmitriptan can be decreased when combined with Caffeine.Approved, Investigational
ZolpidemThe metabolism of Zolpidem can be decreased when combined with Caffeine.Approved
Food InteractionsNot Available
References
Synthesis Reference

Kaspar Bott, "Preparation of caffeine." U.S. Patent US4380631, issued December, 1976.

US4380631
General References
  1. Nathanson JA: Caffeine and related methylxanthines: possible naturally occurring pesticides. Science. 1984 Oct 12;226(4671):184-7. [PubMed:6207592 ]
  2. Haskell CF, Kennedy DO, Wesnes KA, Milne AL, Scholey AB: A double-blind, placebo-controlled, multi-dose evaluation of the acute behavioural effects of guarana in humans. J Psychopharmacol. 2007 Jan;21(1):65-70. Epub 2006 Mar 13. [PubMed:16533867 ]
  3. Smit HJ, Gaffan EA, Rogers PJ: Methylxanthines are the psycho-pharmacologically active constituents of chocolate. Psychopharmacology (Berl). 2004 Nov;176(3-4):412-9. Epub 2004 May 5. [PubMed:15549276 ]
  4. Benjamin LT Jr, Rogers AM, Rosenbaum A: Coca-Cola, caffeine, and mental deficiency: Harry Hollingworth and the Chattanooga trial of 1911. J Hist Behav Sci. 1991 Jan;27(1):42-55. [PubMed:2010614 ]
  5. Nehlig A, Daval JL, Debry G: Caffeine and the central nervous system: mechanisms of action, biochemical, metabolic and psychostimulant effects. Brain Res Brain Res Rev. 1992 May-Aug;17(2):139-70. [PubMed:1356551 ]
External Links
ATC CodesV04CG30 — Caffeine and sodium benzoateR03DA20 — Combinations of xanthinesN06BC01 — Caffeine
AHFS Codes
  • 28:08.92
  • 28:20.00
  • 28:20.92
  • 92:02.00*
PDB EntriesNot Available
FDA labelDownload (37.7 KB)
MSDSDownload (76.1 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceHealthy Volunteers1
0CompletedBasic ScienceVoice Disorders1
0CompletedTreatmentType 2 Diabetes Mellitus1
0Unknown StatusBasic SciencePsychotropic Drugs Effects1
1Active Not RecruitingBasic ScienceNash1
1Active Not RecruitingOtherNeoplasms1
1Active Not RecruitingTreatmentHealthy Volunteers1
1Active Not RecruitingTreatmentPsoriasis1
1Active Not RecruitingTreatmentCMET-dysregulated Advanced Solid Tumors1
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailablePain, Chronic1
1CompletedNot AvailableTumors, Solid1
1CompletedBasic ScienceAlzheimer's Disease (AD) / Metabolism1
1CompletedBasic ScienceDrug Biotransformation / Membrane Transport1
1CompletedBasic ScienceDrug Interactions1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics of Caffeine / Pharmacokinetics of Repaglinide1
1CompletedBasic ScienceMalignant Neoplasm of Prostate / Pharmacokinetics of Caffeine / Pharmacokinetics of Dextromethorphan1
1CompletedBasic ScienceRheumatoid Arthritis1
1CompletedBasic ScienceModerate, refractory Atopic dermatitis1
1CompletedDiagnosticCytochrome / Pharmacokinetics1
1CompletedDiagnosticDrug Interactions1
1CompletedDiagnosticHealthy Volunteers1
1CompletedDiagnosticMolecular Imaging / Molecular Imaging [E01.370.350.557]1
1CompletedHealth Services ResearchCognitively Healthy Subjects Influenced by Psychoactive Drugs1
1CompletedHealth Services ResearchHealthy Volunteers1
1CompletedPreventionEndotoxaemia1
1CompletedTreatmentAdvanced Solid Tumors, Excluding Breast Cancer1
1CompletedTreatmentAnemias / Healthy Volunteers1
1CompletedTreatmentCompulsive Behavior / Substance Dependence1
1CompletedTreatmentDrug Interactions1
1CompletedTreatmentHealthy Volunteers8
1CompletedTreatmentHepatitis C, Chronic1
1CompletedTreatmentInfectious Diseases1
1CompletedTreatmentPsoriasis1
1Not Yet RecruitingBasic ScienceLiver Diseases1
1RecruitingBasic ScienceNeoplasms Metastasis1
1RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1Unknown StatusBasic ScienceHealthy Volunteers3
1, 2CompletedBasic ScienceDependence, Cocaine1
1, 2RecruitingSupportive CareNarcolepsy1
1, 2WithdrawnTreatmentAmblyopia1
2CompletedPreventionAdenoidectomy / Postoperative Complications / Sleep Apnea, Obstructive / Tonsillectomy1
2CompletedSupportive CareCancers / Pain1
2CompletedTreatmentBMI >30 kg/m21
2CompletedTreatmentParkinson's Disease (PD)1
2Not Yet RecruitingTreatmentApnea1
2Not Yet RecruitingTreatmentPostoperative paralytic ileus1
2RecruitingPreventionRetinopathy of Prematurity1
2TerminatedTreatmentDyspnea1
2, 3CompletedTreatmentCocaine Related Disorders1
2, 3CompletedTreatmentExcessive Daytime Somnolence / Parkinson's Disease (PD)1
2, 3RecruitingTreatmentCaffeine Withdrawal / Migraines1
3CompletedNot AvailableMyocardial Infarction (MI)1
3CompletedBasic ScienceBMI >30 kg/m21
3CompletedPreventionApnea / Preterm Infants1
3CompletedPreventionCoronary Heart Disease (CHD)1
3CompletedPreventionPrimary apnea of premature newborns1
3CompletedTreatmentDysmenorrhea1
3CompletedTreatmentIntermittent Claudication1
3CompletedTreatmentMigraine Disorders1
3CompletedTreatmentPain1
3CompletedTreatmentParkinson's Disease (PD)1
3CompletedTreatmentPostoperative pain / Tooth Diseases1
3CompletedTreatmentPrimary apnea of premature newborns2
3CompletedTreatmentAcute Rhinitis1
3CompletedTreatmentArterial hypoxia1
3Not Yet RecruitingTreatmentMechanical Low Back Pain / Postural Low Back Pain1
3Not Yet RecruitingTreatmentPain1
3RecruitingTreatmentBack Pain / Cervical Pain1
3Unknown StatusTreatmentHeadaches1
3WithdrawnTreatmentPain1
4CompletedBasic ScienceFeeling Anxious1
4CompletedBasic ScienceRejection, Transplant1
4CompletedPreventionAtherosclerosis / Cardiovascular Disease (CVD)1
4CompletedPreventionBrain Injury / Intraventricular Hemorrhage / Primary apnea of premature newborns1
4CompletedPreventionCaffeine1
4CompletedPreventionEnergy Expenditure1
4CompletedTreatmentCardiovascular Disease (CVD) / Ischemia-Reperfusion Injury1
4CompletedTreatmentElderly / Healthy Volunteers1
4CompletedTreatmentGastrointestinal Stroma Tumors / Non Small-cell Lung Cancer / Renal-cell Cancer1
4CompletedTreatmentHealthy Elderly Citizens1
4CompletedTreatmentPain, Migraine1
4CompletedTreatmentAcute Rhinitis1
4Not Yet RecruitingTreatmentCrohn's Disease (CD) / Ulcerative Colitis (UC)1
4RecruitingBasic ScienceType 2 Diabetes Mellitus1
4RecruitingPreventionAnaesthesia therapy1
4RecruitingPreventionBPD - Bronchopulmonary Dysplasia / Hemodynamics Instability / Intubations / Primary apnea of premature newborns1
4TerminatedOtherPain1
4TerminatedTreatmentMigrainous Headache1
4Unknown StatusScreeningHealthy Volunteers1
4Unknown StatusTreatmentDependence, Cocaine1
Not AvailableActive Not RecruitingNot AvailableAutonomic Nervous System / Cardiorespiratory Parameters1
Not AvailableActive Not RecruitingNot AvailableCaffeine / Premature Newborns / Primary apnea of premature newborns1
Not AvailableActive Not RecruitingScreeningAlcoholism1
Not AvailableCompletedNot AvailableAffect / Caffeine / Cognitive Ability, General / Other Stimulant Use, Unspecified1
Not AvailableCompletedNot AvailableAutonomic Nervous System1
Not AvailableCompletedNot AvailableCaffeine / Ischemia-Reperfusion Injury / Ischemic Preconditioning1
Not AvailableCompletedNot AvailableDrug Half Life / Pharmacokinetics / Placebo Effect1
Not AvailableCompletedNot AvailableGrowth Hormone Deficiency, Dwarfism1
Not AvailableCompletedNot AvailableHealthy Volunteers / Hypertensive1
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Eating Behavior1
Not AvailableCompletedBasic ScienceHealthy Volunteers3
Not AvailableCompletedBasic ScienceArterial hypoxia / Hyperemia1
Not AvailableCompletedDiagnosticCoronary Artery Disease1
Not AvailableCompletedDiagnosticSleep Apnea Syndrome1
Not AvailableCompletedPreventionBMI >30 kg/m21
Not AvailableCompletedPreventionCaffeine1
Not AvailableCompletedPreventionProphylaxis against postoperative nausea and vomiting1
Not AvailableCompletedTreatmentApnea / Bronchiolitis / Caffeine1
Not AvailableCompletedTreatmentNonvalvular Atrial Fibrillation / Supraventricular Tachycardia (SVT)1
Not AvailableCompletedTreatmentPlacebo Effect / Placebo Mechanisms of Action1
Not AvailableCompletedTreatmentPost Dural Puncture Headache1
Not AvailableRecruitingNot AvailableDepressive State1
Not AvailableRecruitingBasic ScienceCaffeine / Schizophrenic Disorders1
Not AvailableRecruitingOtherHealthy Volunteers1
Not AvailableRecruitingPreventionChronic Lung Disease of Prematurity / Primary apnea of premature newborns1
Not AvailableRecruitingPreventionDiverticulitis / Laparoscopic Colectomy Without Stoma Formation / Neoplasms, Colorectal / Postoperative paralytic ileus1
Not AvailableSuspendedNot AvailableIschemia-Reperfusion Injury1
Not AvailableTerminatedScreeningCytochrome P450 Phenotype and Genotype Metrics1
Not AvailableTerminatedTreatmentApnea / Premature Babies / Respiratory Failure1
Not AvailableTerminatedTreatmentEnlargement of Tonsil or Adenoid / Obstructive Sleep Apnea (OSA)1
Not AvailableUnknown StatusTreatmentPerceived Alcohol Intoxication1
Pharmacoeconomics
Manufacturers
  • Mead johnson and co
  • App pharmaceuticals llc
  • Luitpold pharmaceuticals inc
  • Paddock laboratories inc
  • Sun pharmaceutical industries ltd
Packagers
Dosage forms
FormRouteStrength
Tablet, multilayerOral200 1/1
CapsuleOral175 mg
TabletOral175 mg
TabletOral100 mg
Tablet, coatedOral200 mg/1
Tablet, film coatedOral200 mg/1
Tablet, effervescentOral
SyrupOral
CapsuleOral
TabletOral
InjectionIntravenous20 mg/mL
Tablet, multilayerOral200 mg/200mg
Injection, solutionIntramuscular; Intravenous125 mg/mL
Injection, solutionIntravenous20 mg/mL
SolutionIntravenous20 mg/mL
SolutionOral20 mg/mL
TabletOral200 mg
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral
Capsule, gelatin coatedOral
Tablet, coatedOral
SolutionOral
LiquidOral
GranuleOral
Capsule, coatedOral
TabletTopical
PowderOral
Tablet, coatedOral100 mg/1
Capsule, liquid filledOral200 mg/1
Capsule, liquid filledOral
SuppositoryRectal
CreamTopical
CreamTopical5 mg/1000mL
Tablet, multilayerOral
Injection, solution; solutionIntravenous; Oral20 mg/ml
CapsuleOral100 mg
WaferOral60 mg
TabletOral200 mg/1
LiquidOral50 mg
Prices
Unit descriptionCostUnit
Migergot 12 2-100 mg Suppository Box105.43USD box
Cafcit 20 mg/ml oral soln16.4USD ml
Cafcit 20 mg/ml vial16.4USD ml
Caffeine cit 20 mg/ml oral sol15.21USD ml
Caffeine citrate 20 mg/ml vial12.8USD ml
Migergot suppository7.39USD suppository
Esgic tablet2.5USD tablet
Esgic 50-325-40 mg tablet2.27USD tablet
Darvon-n 100 mg tablet1.95USD tablet
Esgic-plus 50-500-40 mg tablet1.95USD tablet
Cafergot 1-100 mg tablet1.9USD tablet
Darvon 65 mg pulvule1.49USD each
Fioricet 50-325-40 mg tablet1.24USD tablet
Butalb-apap-caff 50-500-40 tablet1.2USD tablet
Butalb-apap-caff 50-325-40 tablet0.44USD tablet
Caffeine citrate powder0.36USD g
Propoxyphene hcl 65 mg capsule0.33USD capsule
Vivarin 200 mg caplet0.17USD caplet
Vivarin 200 mg tablet0.17USD tablet
No doz 200 mg caplet0.16USD caplet
Caffeine citrated powder purif0.13USD g
Stay awake 200 mg tablet0.1USD tablet
CVS Pharmacy caffeine 200 mg tablet0.09USD tablet
Ra stay awake 100 mg tablet0.09USD tablet
Caffeine powder0.07USD g
Caffeine 200 mg tablet0.01USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5972916 No1997-07-142017-07-14Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)238 °CPhysProp
water solubility2.16E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.07HANSCH,C ET AL. (1995)
logS-0.97ADME Research, USCD
Caco2 permeability-4.41ADME Research, USCD
pKa10.4 (at 40 °C)DEAN,JA (1985)
Predicted Properties
PropertyValueSource
Water Solubility11.0 mg/mLALOGPS
logP-0.24ALOGPS
logP-0.55ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)-0.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.44 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity49.83 m3·mol-1ChemAxon
Polarizability18.95 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9974
Blood Brain Barrier+0.9935
Caco-2 permeable+0.633
P-glycoprotein substrateNon-substrate0.7572
P-glycoprotein inhibitor INon-inhibitor0.8086
P-glycoprotein inhibitor IINon-inhibitor0.8471
Renal organic cation transporterNon-inhibitor0.8872
CYP450 2C9 substrateNon-substrate0.7484
CYP450 2D6 substrateNon-substrate0.5869
CYP450 3A4 substrateNon-substrate0.5305
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9906
CYP450 2D6 inhibitorNon-inhibitor0.9836
CYP450 2C19 inhibitorNon-inhibitor0.9927
CYP450 3A4 inhibitorNon-inhibitor0.9618
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9924
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9359
BiodegradationReady biodegradable0.6696
Rat acute toxicity2.9741 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8925
hERG inhibition (predictor II)Non-inhibitor0.8702
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Download (8.61 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)splash10-0536-3900000000-a9e112713ffae6dabdaaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)splash10-0536-2900000000-8cdcd005b2e7622a02a3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-052f-0900000000-f1084acfddb240696073View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-05nf-6900000000-8670a644cee5d9de78d4View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0536-3900000000-4430852b279a72e34822View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-0900000000-51898e93480e848d7da1View in MoNA
GC-MSGC-MS Spectrum - CI-Bsplash10-0002-0900000000-2aed5d425b6a95add5dbView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0a4l-4900000000-3ff72dace6687d242f1fView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-1900000000-2ba1fae6e27c7b836984View in MoNA
GC-MSGC-MS Spectrum - CI-Bsplash10-0002-0900000000-fd859aeb416e320d6379View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0900000000-447fc72b2c709e2e18a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-5e3b29de16ad91c79fe0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-d6f6c52ac36c8f25a500View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0006-0900000000-cddd24399d942b1ac97cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (Unknown) , Positivesplash10-0002-0900000000-2aed5d425b6a95add5dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0a4l-4900000000-3ff72dace6687d242f1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-0006-1900000000-2ba1fae6e27c7b836984View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-60) , Positivesplash10-0002-0900000000-63b9ef42a3e8d59e9997View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0900000000-185b3d97d8857a0f269dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0002-0900000000-f8a0c0dd9f5c4a272eafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-1900000000-dd8e35226d0704aa657dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-01x9-9800000000-70e3b0eb52481c39d191View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001l-9100000000-6d428a5571beb0e3fed4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-98bec16f898808c3de68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0002-0900000000-b112e4e059e1ecf98c5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-695d910d49fc0beb1d54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-094879886a2e72bf0c56View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-fa38c865089a3a05f287View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000b-0900000000-0e82732a924c974dd0c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-761710441aa2c1c3ac68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0900000000-c10af6eda9a9a4094715View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-3900000000-141118b1a93b4d48b2d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-c8bd8cccb7dd6c66bb42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-2c8c1760161edd358026View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-5900000000-260de4a79007e853e4bbView in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-8900000000-68b5e9aa3404fb3d8d3aView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents6-oxopurines / Alkaloids and derivatives / Pyrimidones / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds
SubstituentsXanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Pyrimidone / N-substituted imidazole / Pyrimidine / Azole / Imidazole / Heteroaromatic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorspurine alkaloid, trimethylxanthine (CHEBI:27732 ) / Purine alkaloids (C07481 ) / a small molecule (1-3-7-TRIMETHYLXANTHINE )

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonistmultitarget
General Function:
Purine nucleoside binding
Specific Function:
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
ADORA1
Uniprot ID:
P30542
Uniprot Name:
Adenosine receptor A1
Molecular Weight:
36511.325 Da
References
  1. Gaytan SP, Saadani-Makki F, Bodineau L, Frugiere A, Larnicol N, Pasaro R: Effect of postnatal exposure to caffeine on the pattern of adenosine A1 receptor distribution in respiration-related nuclei of the rat brainstem. Auton Neurosci. 2006 Jun 30;126-127:339-46. Epub 2006 May 15. [PubMed:16702031 ]
  2. Wang SJ: Caffeine facilitation of glutamate release from rat cerebral cortex nerve terminals (synaptosomes) through activation protein kinase C pathway: an interaction with presynaptic adenosine A1 receptors. Synapse. 2007 Jun;61(6):401-11. [PubMed:17372967 ]
  3. Rieg T, Schnermann J, Vallon V: Adenosine A1 receptors determine effects of caffeine on total fluid intake but not caffeine appetite. Eur J Pharmacol. 2007 Jan 26;555(2-3):174-7. Epub 2006 Oct 25. [PubMed:17126319 ]
  4. Mustafa S, Venkatesh P, Pasha K, Mullangi R, Srinivas NR: Altered intravenous pharmacokinetics of topotecan in rats with acute renal failure (ARF) induced by uranyl nitrate: do adenosine A1 antagonists (selective/non-selective) normalize the altered topotecan kinetics in ARF? Xenobiotica. 2006 Dec;36(12):1239-58. [PubMed:17162470 ]
  5. Listos J, Malec D, Fidecka S: Adenosine receptor antagonists intensify the benzodiazepine withdrawal signs in mice. Pharmacol Rep. 2006 Sep-Oct;58(5):643-51. [PubMed:17085856 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonistmultitarget
General Function:
Identical protein binding
Specific Function:
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name:
ADORA2A
Uniprot ID:
P29274
Uniprot Name:
Adenosine receptor A2a
Molecular Weight:
44706.925 Da
References
  1. Riksen NP, Franke B, van den Broek P, Smits P, Rongen GA: The 1976C>T polymorphism in the adenosine A2A receptor gene does not affect the vasodilator response to adenosine in humans in vivo. Pharmacogenet Genomics. 2007 Jul;17(7):551-4. [PubMed:17558310 ]
  2. Zhao G, Messina E, Xu X, Ochoa M, Sun HL, Leung K, Shryock J, Belardinelli L, Hintze TH: Caffeine attenuates the duration of coronary vasodilation and changes in hemodynamics induced by regadenoson (CVT-3146), a novel adenosine A2A receptor agonist. J Cardiovasc Pharmacol. 2007 Jun;49(6):369-75. [PubMed:17577101 ]
  3. Cornelis MC, El-Sohemy A, Campos H: Genetic polymorphism of the adenosine A2A receptor is associated with habitual caffeine consumption. Am J Clin Nutr. 2007 Jul;86(1):240-4. [PubMed:17616786 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents.
Gene Name:
PDE4B
Uniprot ID:
Q07343
Uniprot Name:
cAMP-specific 3',5'-cyclic phosphodiesterase 4B
Molecular Weight:
83342.695 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Daly JW: Caffeine analogs: biomedical impact. Cell Mol Life Sci. 2007 Aug;64(16):2153-69. [PubMed:17514358 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Voltage-gated calcium channel activity
Specific Function:
Calcium channel that mediates the release of Ca(2+) from the sarcoplasmic reticulum into the cytoplasm and thereby plays a key role in triggering muscle contraction following depolarization of T-tubules. Repeated very high-level exercise increases the open probability of the channel and leads to Ca(2+) leaking into the cytoplasm. Can also mediate the release of Ca(2+) from intracellular stores ...
Gene Name:
RYR1
Uniprot ID:
P21817
Uniprot Name:
Ryanodine receptor 1
Molecular Weight:
565170.715 Da
References
  1. Daly JW: Caffeine analogs: biomedical impact. Cell Mol Life Sci. 2007 Aug;64(16):2153-69. [PubMed:17514358 ]
Kind
Protein group
Organism
Human
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a higher affinity for cGMP than for cAMP.
Components:
NameUniProt IDDetails
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AP54750 Details
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BQ01064 Details
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CQ14123 Details
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10AQ9Y233 Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4AP27815 Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4BQ07343 Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4CQ08493 Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4DQ08499 Details
cAMP-specific 3',5'-cyclic phosphodiesterase 7BQ9NP56 Details
cGMP-dependent 3',5'-cyclic phosphodiesteraseO00408 Details
cGMP-inhibited 3',5'-cyclic phosphodiesterase AQ14432 Details
cGMP-inhibited 3',5'-cyclic phosphodiesterase BQ13370 Details
cGMP-specific 3',5'-cyclic phosphodiesteraseO76074 Details
Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'P51160 Details
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11AQ9HCR9 Details
High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7AQ13946 Details
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8AO60658 Details
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8BO95263 Details
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9AO76083 Details
Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alphaP16499 Details
Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit betaP35913 Details
References
  1. Ribeiro JA, Sebastiao AM: Caffeine and adenosine. J Alzheimers Dis. 2010;20 Suppl 1:S3-15. doi: 10.3233/JAD-2010-1379. [PubMed:20164566 ]
  2. Essayan DM: Cyclic nucleotide phosphodiesterases. J Allergy Clin Immunol. 2001 Nov;108(5):671-80. [PubMed:11692087 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Transcription factor binding
Specific Function:
Serine/threonine-protein kinase that acts as a molecular sensor for DNA damage. Involved in DNA non-homologous end joining (NHEJ) required for double-strand break (DSB) repair and V(D)J recombination. Must be bound to DNA to express its catalytic properties. Promotes processing of hairpin DNA structures in V(D)J recombination by activation of the hairpin endonuclease artemis (DCLRE1C). The asse...
Gene Name:
PRKDC
Uniprot ID:
P78527
Uniprot Name:
DNA-dependent protein kinase catalytic subunit
Molecular Weight:
469084.155 Da
References
  1. Foukas LC, Daniele N, Ktori C, Anderson KE, Jensen J, Shepherd PR: Direct effects of caffeine and theophylline on p110 delta and other phosphoinositide 3-kinases. Differential effects on lipid kinase and protein kinase activities. J Biol Chem. 2002 Oct 4;277(40):37124-30. Epub 2002 Jul 26. [PubMed:12145276 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Phosphatidylinositol-4,5-bisphosphate 3-kinase activity
Specific Function:
Phosphoinositide-3-kinase (PI3K) that phosphorylates PftdIns(4,5)P2 (Phosphatidylinositol 4,5-bisphosphate) to generate phosphatidylinositol 3,4,5-trisphosphate (PIP3). PIP3 plays a key role by recruiting PH domain-containing proteins to the membrane, including AKT1 and PDPK1, activating signaling cascades involved in cell growth, survival, proliferation, motility and morphology. Mediates immun...
Gene Name:
PIK3CD
Uniprot ID:
O00329
Uniprot Name:
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
Molecular Weight:
119478.065 Da
References
  1. Foukas LC, Daniele N, Ktori C, Anderson KE, Jensen J, Shepherd PR: Direct effects of caffeine and theophylline on p110 delta and other phosphoinositide 3-kinases. Differential effects on lipid kinase and protein kinase activities. J Biol Chem. 2002 Oct 4;277(40):37124-30. Epub 2002 Jul 26. [PubMed:12145276 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein serine/threonine kinase activity
Specific Function:
Phosphoinositide-3-kinase (PI3K) that phosphorylates PtdIns (Phosphatidylinositol), PtdIns4P (Phosphatidylinositol 4-phosphate) and PtdIns(4,5)P2 (Phosphatidylinositol 4,5-bisphosphate) to generate phosphatidylinositol 3,4,5-trisphosphate (PIP3). PIP3 plays a key role by recruiting PH domain-containing proteins to the membrane, including AKT1 and PDPK1, activating signaling cascades involved in...
Gene Name:
PIK3CA
Uniprot ID:
P42336
Uniprot Name:
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
Molecular Weight:
124283.025 Da
References
  1. Foukas LC, Daniele N, Ktori C, Anderson KE, Jensen J, Shepherd PR: Direct effects of caffeine and theophylline on p110 delta and other phosphoinositide 3-kinases. Differential effects on lipid kinase and protein kinase activities. J Biol Chem. 2002 Oct 4;277(40):37124-30. Epub 2002 Jul 26. [PubMed:12145276 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Phosphatidylinositol-4,5-bisphosphate 3-kinase activity
Specific Function:
Phosphoinositide-3-kinase (PI3K) that phosphorylates PtdIns (Phosphatidylinositol), PtdIns4P (Phosphatidylinositol 4-phosphate) and PtdIns(4,5)P2 (Phosphatidylinositol 4,5-bisphosphate) to generate phosphatidylinositol 3,4,5-trisphosphate (PIP3). PIP3 plays a key role by recruiting PH domain-containing proteins to the membrane, including AKT1 and PDPK1, activating signaling cascades involved in...
Gene Name:
PIK3CB
Uniprot ID:
P42338
Uniprot Name:
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform
Molecular Weight:
122761.225 Da
References
  1. Foukas LC, Daniele N, Ktori C, Anderson KE, Jensen J, Shepherd PR: Direct effects of caffeine and theophylline on p110 delta and other phosphoinositide 3-kinases. Differential effects on lipid kinase and protein kinase activities. J Biol Chem. 2002 Oct 4;277(40):37124-30. Epub 2002 Jul 26. [PubMed:12145276 ]
Kind
Protein group
Organism
Human
Pharmacological action
unknown
General Function:
Phosphatidylinositol binding
Specific Function:
Intracellular channel that mediates calcium release from the endoplasmic reticulum following stimulation by inositol 1,4,5-trisphosphate. Involved in the regulation of epithelial secretion of electrolytes and fluid through the interaction with AHCYL1 (By similarity). Plays a role in ER stress-induced apoptosis. Cytoplasmic calcium released from the ER triggers apoptosis by the activation of CaM kinase II, eventually leading to the activation of downstream apoptosis pathways (By similarity).
Components:
NameUniProt IDDetails
Inositol 1,4,5-trisphosphate receptor type 1Q14643 Details
Inositol 1,4,5-trisphosphate receptor type 2Q14571 Details
Inositol 1,4,5-trisphosphate receptor type 3Q14573 Details
References
  1. Parker I, Ivorra I: Caffeine inhibits inositol trisphosphate-mediated liberation of intracellular calcium in Xenopus oocytes. J Physiol. 1991 Feb;433:229-40. [PubMed:1844813 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein serine/threonine kinase activity
Specific Function:
Serine/threonine protein kinase which activates checkpoint signaling upon double strand breaks (DSBs), apoptosis and genotoxic stresses such as ionizing ultraviolet A light (UVA), thereby acting as a DNA damage sensor. Recognizes the substrate consensus sequence [ST]-Q. Phosphorylates 'Ser-139' of histone variant H2AX/H2AFX at double strand breaks (DSBs), thereby regulating DNA damage response ...
Gene Name:
ATM
Uniprot ID:
Q13315
Uniprot Name:
Serine-protein kinase ATM
Molecular Weight:
350684.105 Da
References
  1. Sarkaria JN, Busby EC, Tibbetts RS, Roos P, Taya Y, Karnitz LM, Abraham RT: Inhibition of ATM and ATR kinase activities by the radiosensitizing agent, caffeine. Cancer Res. 1999 Sep 1;59(17):4375-82. [PubMed:10485486 ]
  2. Blasina A, Price BD, Turenne GA, McGowan CH: Caffeine inhibits the checkpoint kinase ATM. Curr Biol. 1999 Oct 7;9(19):1135-8. [PubMed:10531013 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Uniprot Name:
Cytochrome P450 1A2
Molecular Weight:
58293.76 Da
References
  1. Brosen K: Drug interactions and the cytochrome P450 system. The role of cytochrome P450 1A2. Clin Pharmacokinet. 1995;29 Suppl 1:20-5. [PubMed:8846619 ]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  4. Hickman D, Wang JP, Wang Y, Unadkat JD: Evaluation of the selectivity of In vitro probes and suitability of organic solvents for the measurement of human cytochrome P450 monooxygenase activities. Drug Metab Dispos. 1998 Mar;26(3):207-15. [PubMed:9492382 ]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Uniprot Name:
Cytochrome P450 3A4
Molecular Weight:
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Uniprot Name:
Cytochrome P450 3A5
Molecular Weight:
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Uniprot Name:
Cytochrome P450 3A7
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Uniprot Name:
Cytochrome P450 2E1
Molecular Weight:
56848.42 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Uniprot Name:
Cytochrome P450 2C8
Molecular Weight:
55824.275 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Uniprot Name:
Cytochrome P450 2C9
Molecular Weight:
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Uniprot Name:
Cytochrome P450 1A1
Molecular Weight:
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compou...
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Uniprot Name:
Cytochrome P450 1B1
Molecular Weight:
60845.33 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Uniprot Name:
Cytochrome P450 2D6
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Uniprot Name:
Multidrug resistance protein 1
Molecular Weight:
141477.255 Da
References
  1. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. [PubMed:10213372 ]
  2. Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [PubMed:12954186 ]
Drug created on June 13, 2005 07:24 / Updated on August 08, 2017 11:03