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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. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
1-methyltheobromineNot AvailableNot Available
1,3,7-Trimethyl-2,6-dioxopurineNot AvailableNot Available
1,3,7-trimethylpurine-2,6-dioneNot AvailableNot Available
1,3,7-trimethylxanthineNot AvailableNot Available
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dionNot AvailableNot Available
7-methyltheophyllineNot AvailableNot Available
Anhydrous caffeineNot AvailableNot Available
CafeínaSpanishNot Available
CaféineFrenchNot Available
CaffeineNot AvailableNot Available
CoffeinGermanNot Available
GuaranineNot AvailableNot Available
KoffeinGermanNot Available
MateínaSpanishNot Available
MethyltheobromineNot AvailableNot Available
TeinaNot AvailableNot Available
TheinNot AvailableNot Available
TheineNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cafcitinjection20 mg/mLintravenousBedford Laboratories2008-11-042016-04-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cafcitsolution20 mg/mLoralBedford Laboratories2008-11-042016-05-29Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Caffeine Citrateinjection, solution20 mg/mLintravenousAmerican Regent, Inc.2007-09-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citratesolution20 mg/mLoralPaddock Laboratories, LLC2006-09-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citrateinjection20 mg/mLintravenousPaddock Laboratories, LLC2006-09-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citratesolution20 mg/mLintravenousSagent Pharmaceuticals2012-09-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citratesolution20 mg/mLoralSagent Pharmaceuticals2012-09-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citrateinjection20 mg/mLintravenousSun Pharma Global FZE2009-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citrateinjection20 mg/mLintravenousSun Pharma Global FZE2014-06-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citratesolution20 mg/mLoralSun Pharma Global FZE2009-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citratesolution20 mg/mLoralSun Pharma Global FZE2014-06-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citrateinjection20 mg/mLintravenousExela Pharma Sciences, LLC2006-09-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citratesolution20 mg/mLoralREMEDYREPACK INC.2013-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citratesolution20 mg/mLoralREMEDYREPACK INC.2013-10-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citratesolution20 mg/mLoralAPP Pharmaceuticals, LLC2009-11-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citrateinjection, solution20 mg/mLintravenousFresenius Kabi USA, LLC2009-11-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeine Citrateinjection, solution20 mg/mLintravenousFresenius Kabi USA, LLC2009-11-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Good Sense Stay Awaketablet200 mgoralL Perrigo Company1993-03-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Vivarintablet200 mgoralGlaxo Smith Kline Consumer Healthcare Lp2010-11-082015-08-31Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awake Maximum Strengthtablet200 mgoralWALGREEN CO.1996-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Awaketablet200 mgoralWALGREEN CO.1998-04-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralMajor Pharmaceuticals1992-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Alert Aidtablet200 mgoralRite Aid1992-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralRite Aid1998-04-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralStephen L. La France Pharmacy, Inc.1992-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Maximum Strength Stay Awaketablet200 mgoralSafeway1992-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Good Neighbor Pharmacy Stay Awaketablet200 mgoralAmerisource Bergen2001-07-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralKroger Company1994-06-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralGreenbrier International, Inc.1996-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Topcare Stay Awake maximum strengthtablet200 mgoralTopco Associates LLC1993-12-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Leader Alertness Aidtablet200 mgoralCardinal Health1994-02-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralH E B1996-03-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralSUPERVALU INC.1992-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Equaline Stay Awaketablet200 mgoralSupervalu Inc2004-08-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awake Maximum Strengthtablet200 mgoralSUPERVALU INC.1998-04-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Drowz Away Maximum strengthtablet200 mgoralCare One (American Sales Company)2014-03-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Drowz Away Maximum strengthtablet200 mgoralCare One (American Sales Company)2010-08-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralHy Vee Inc1996-05-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Vivarintablet200 mgoralMeda Consumer Healthcare Inc.2014-06-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Vivarintablet200 mgoralMeda Consumer Healthcare Inc.2012-01-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralWal Mart Stores Inc1992-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sunmark Stay Awaketablet200 mgoralMc Kesson2003-08-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Alerttablet, film coated200 mgoralTime Cap Labs, Inc2011-11-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Smart Sense Stay Awaketablet200 mgoralKmart Corporation2010-12-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sohmed Alertness Aidtablet200 mgoralSOHM Inc.2013-08-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Alerttablet200 mgoralL.N.K. International, Inc.1992-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pep-back Peak Performancetablet, film coated200 mgoralAlva Amco Pharmacal Companies, Inc.2007-03-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pep-back Ultratablet, film coated200 mgoralAlva Amco Pharmacal Companies, Inc.1993-04-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Diurex Ultratablet, film coated100 mgoralAlva Amco Pharmacal Companies, Inc.2005-09-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Diurex WaterCapstablet, film coated200 mgoralAlva Amco Pharmacal Companies, Inc.2009-04-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Allertness Aidtablet200 mgoralSelect Corporation2012-10-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralNational Distribution Network (Smart Choice)2014-05-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralArmy and Air Force Exchange Service1996-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralWestern Family Foods, Inc.2014-02-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralWestern Family Foods, Inc.2010-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralFreds Inc2013-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralFreds Inc2014-03-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Healthy Accents Stay Awaketablet200 mgoralDZA Brands LLC2008-02-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Alerttablet200 mgoralDolgencorp, LLC1992-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralPublix Super Markets Inc1998-01-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralSalado Sales, Inc.1992-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeinetablet200 mgoralAAA Pharmaceutical, Inc.2012-12-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Caffeinetablet200 mgoralWOONSOCKET PRESCRIPTION CENTER,INCORPORATED1992-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Maximum Strength Caffeinetablet200 mgoralWOONSOCKET PRESCRIPTION CENTER,INCORPORATED1998-04-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nano Ppccream1.25; 2.5 mg/250mL; mg/250mLtopicalYBK Investment, INC2013-11-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralKinray Inc.2013-05-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Health Mart Stay Awaketablet200 mgoralMc Kesson2011-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralChain Drug Marketing Association2014-06-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralBest Choice (Valu Merchandisers Company)2014-04-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awake Maximum strengthtablet200 mgoralValu Merchandisers Company (Best Choice)2010-09-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralGREAT LAKES WHOLESALE, MARKETING, & SALES, INC.1992-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Circle K Nosnoozetablet200 mgoralLil' Drug Store Products, Inc2014-11-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Lil Drug Store Nosnoozetablet200 mgoralLil' Drug Store Products, Inc.2011-02-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Lil Drug Store Nosnoozetablet200 mgoralLil' Drug Store Products, Inc.2011-02-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralWin Co Foods, Llc1996-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Allertness Aidtablet200 mgoralChain Drug Consortium2014-11-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Conrx Alerttablet200 mgoralEagle Distributors,Inc.2013-02-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Stay Awaketablet200 mgoralNash Finch Company1992-11-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
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
Brand NameIngredients
A & C Tablets with CodeineAcetylsalicylic Acid + Caffeine + Codeine Phosphate
AC&CAcetylsalicylic Acid + Caffeine + Codeine Phosphate
Acet 2Acetaminophen + Caffeine + Codeine Phosphate
Acet 3Acetaminophen + Caffeine + Codeine Phosphate
AlagesicCaffeine + Butalbital + Acetaminophen
Alka-Seltzer Morning ReliefAcetylsalicylic Acid + Caffeine
AnacinAcetylsalicylic Acid + Caffeine
AntidolAcetylsalicylic Acid + Caffeine
Arco Pain TabAcetylsalicylic Acid + Caffeine Citrate
Astone CapAcetylsalicylic Acid + Caffeine
AtasolAcetaminophen + Caffeine Citrate + Codeine Phosphate
CafergotCaffeine + Ergotamine Tartrate
Cafergot PBBelladonna + Caffeine + Ergotamine (Ergotamine Tartrate) + Pentobarbital
CalmineAcetylsalicylic Acid + Caffeine
CapacetCaffeine + Butalbital + Acetaminophen
CodaminophenAcetaminophen + Caffeine + Codeine Phosphate
CorytabAcetaminophen + Caffeine + Diphenylpyraline Hydrochloride
CotabsAcetaminophen + Caffeine Citrate + Codeine Phosphate
Darvon N Compound Pulvule 405Acetylsalicylic Acid + Caffeine + Dextropropoxyphene Napsylate
Dolomine 37Acetylsalicylic Acid + Caffeine
DristanAcetylsalicylic Acid + Caffeine + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Emercidin DAcetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
EmertabsAcetaminophen + Caffeine + Phenylpropanolamine Hydrochloride
ErgodrylCaffeine Citrate + Diphenhydramine Hydrochloride + Ergotamine Tartrate
Esgic-PlusCaffeine + Butalbital + Acetaminophen
ExcedrinAcetaminophen + Caffeine
ExdolAcetaminophen + Caffeine Citrate + Codeine Phosphate
FiorinalAcetylsalicylic Acid + Butalbital + Caffeine + Codeine Phosphate
GravergolCaffeine + Dimenhydrinate + Ergotamine Tartrate
HerbopyrineAcetylsalicylic Acid + Caffeine Citrate
InstantineAcetylsalicylic Acid + Caffeine
Invagesiccaffeine + salicylic acid + orphenadrine
MadelonAcetylsalicylic Acid + Caffeine
MegralCaffeine + Cyclizine Hydrochloride + Ergotamine Tartrate
MidolAcetylsalicylic Acid + Caffeine + Cinnamedrine
MIGERGOTCaffeine + Ergotamine
Neo TigolAcetylsalicylic Acid + Aluminum Hydroxide + Caffeine + Magnesium Hydroxide + Passion Flower + Valerian
NervineAcetylsalicylic Acid + Caffeine
NorgesicAcetylsalicylic Acid + Caffeine + Orphenadrine Citrate
Novo AC and CAcetylsalicylic Acid + Caffeine + Codeine Phosphate
Novo-GesicAcetaminophen + Caffeine + Codeine Phosphate
Novo-Propoxyn CompoundAcetylsalicylic Acid + Caffeine + Dextropropoxyphene Hydrochloride
Oradrine 2Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
ORBIVANCaffeine + Butalbital + Acetaminophen
Pain AidAcetylsalicylic Acid + Caffeine
PainexAcetylsalicylic Acid + Caffeine Citrate + Codeine Phosphate
Ratio-Lenoltec No 1Acetaminophen + Caffeine + Codeine Phosphate
Ratio-Lenoltec No 2Acetaminophen + Caffeine + Codeine Phosphate
Ratio-Lenoltec No 3Acetaminophen + Caffeine + Codeine Phosphate
Ratio-TecnalAcetylsalicylic Acid + Butalbital + Caffeine
Sinugex 38Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride
SynalgosCaffeine + Acetylsalicylic acid + Dihydrocodeine
Triaminicin Colds & FluAcetaminophen + Caffeine + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
TrianalAcetylsalicylic Acid + Butalbital + Caffeine
Triatec-8 FortAcetaminophen + Caffeine Citrate + Codeine Phosphate
Tylenol No 1Acetaminophen + Caffeine + Codeine Phosphate
Tylenol No.1 ForteAcetaminophen + Caffeine + Codeine Phosphate
Tylenol No1 Forte Tablets with CodeineAcetaminophen + Caffeine + Codeine Phosphate
Tylenol Ultra ReliefAcetaminophen + Caffeine
Tylenol with Codeine No. 2Acetaminophen + Caffeine + Codeine Phosphate
Tylenol with Codeine No. 3Acetaminophen + Caffeine + Codeine Phosphate
Ultra Headache ReliefAcetaminophen + Caffeine
WigraineBelladonna + Caffeine + Ergotamine Tartrate
Salts
Name/CASStructureProperties
Caffeine citrate
ThumbNot applicableDBSALT000866
Categories
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • Xanthine
  • Purinone
  • 6-oxopurine
  • Purine
  • Imidazopyrimidine
  • Pyrimidone
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azole
  • Urea
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor management of fatigue, orthostatic hypotension, and for the short term treatment of apnea of prematurity in infants.
PharmacodynamicsCaffeine, 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 actionCaffeine 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.
AbsorptionReadily 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 bindingLow (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 eliminationIn young infants, the elimination of caffeine is much slower than that in adults due to immature hepatic and/or renal function.
Half life3 to 7 hours in adults, 65 to 130 hours in neonates
ClearanceNot Available
ToxicityLD50=127 mg/kg (orally in mice)
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Caffeine MetabolismMetabolicSMP00028
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug Reactions
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeAdverse ReactionReference(s)
Cytochrome P450 1A2
Gene symbol: CYP1A2
UniProt: P05177
rs762551 Not AvailableC alleleMyocardial infarction16522833
ADMET
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 substrateNon-inhibitor0.9906
CYP450 2D6 substrateNon-inhibitor0.9836
CYP450 2C19 substrateNon-inhibitor0.9927
CYP450 3A4 substrateNon-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
Pharmacoeconomics
Manufacturers
  • Mead johnson and co
  • App pharmaceuticals llc
  • Luitpold pharmaceuticals inc
  • Paddock laboratories inc
  • Sun pharmaceutical industries ltd
Packagers
Dosage forms
FormRouteStrength
Creamtopical1.25; 2.5 mg/250mL; mg/250mL
Injectionintravenous20 mg/mL
Injection, solutionintravenous20 mg/mL
Solutionintravenous20 mg/mL
Solutionoral20 mg/mL
Tabletoral200 mg
Tablet, film coatedoral100 mg
Tablet, film coatedoral200 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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point238 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.61 KB)
SpectraGC-MSMS/MSLC-MSMS1D NMR2D NMR
References
Synthesis Reference

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

US4380631
General Reference
  1. Nathanson JA: Caffeine and related methylxanthines: possible naturally occurring pesticides. Science. 1984 Oct 12;226(4671):184-7. Pubmed
  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
  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
  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
  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
External Links
ATC CodesN06BC01
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)
Interactions
Drug Interactions
Drug
AcebutololMay enhance the adverse/toxic effect of other Sympathomimetics.
AdenosineCaffeine and Caffeine Containing Products may diminish the therapeutic effect of Adenosine.
AmphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
AtomoxetineMay enhance the hypertensive effect of Sympathomimetics. AtoMOXetine may enhance the tachycardic effect of Sympathomimetics.
BenzphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
ChlorphentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
ClenbuterolMay enhance the adverse/toxic effect of other Sympathomimetics.
DeferasiroxMay increase the serum concentration of CYP1A2 Substrates.
DobutamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DopamineMay enhance the adverse/toxic effect of other Sympathomimetics.
EpinephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
FenoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
FormoterolCaffeine and Caffeine Containing Products may enhance the adverse/toxic effect of Formoterol. Caffeine and Caffeine Containing Products may enhance the hypokalemic effect of Formoterol.
IndacaterolCaffeine and Caffeine Containing Products may enhance the adverse/toxic effect of Indacaterol. Caffeine and Caffeine Containing Products may enhance the hypokalemic effect of Indacaterol.
IsoprenalineMay enhance the adverse/toxic effect of other Sympathomimetics.
LabetalolMay enhance the adverse/toxic effect of other Sympathomimetics.
LinezolidMay enhance the hypertensive effect of Sympathomimetics.
LithiumCaffeine and Caffeine Containing Products may decrease the serum concentration of Lithium.
MephentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
MetaraminolMay enhance the adverse/toxic effect of other Sympathomimetics.
MethamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethoxamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MidodrineMay enhance the adverse/toxic effect of other Sympathomimetics.
NaphazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
NorepinephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
NorfloxacinMay increase the serum concentration of Caffeine and Caffeine Containing Products.
OrciprenalineMay enhance the adverse/toxic effect of other Sympathomimetics.
OxymetazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
Peginterferon alfa-2bMay increase the serum concentration of CYP1A2 Substrates.
PhenmetrazineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenylephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenylpropanolamineMay enhance the adverse/toxic effect of other Sympathomimetics.
RegadenosonCaffeine and Caffeine Containing Products may diminish the vasodilatory effect of Regadenoson.
RitodrineMay enhance the adverse/toxic effect of other Sympathomimetics.
SalmeterolMay enhance the adverse/toxic effect of other Sympathomimetics.
TerbutalineMay enhance the adverse/toxic effect of other Sympathomimetics.
TeriflunomideMay decrease the serum concentration of Caffeine and Caffeine Containing Products.
VemurafenibMay increase the serum concentration of CYP1A2 Substrates.
Food InteractionsNot Available

Targets

1. Adenosine receptor A1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist multitarget

Components

Name UniProt ID Details
Adenosine receptor A1 P30542 Details

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
  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
  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
  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
  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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Adenosine receptor A2a

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist multitarget

Components

Name UniProt ID Details
Adenosine receptor A2a P29274 Details

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
  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
  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
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. cAMP-specific 3',5'-cyclic phosphodiesterase 4B

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4B Q07343 Details

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
  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
  3. Daly JW: Caffeine analogs: biomedical impact. Cell Mol Life Sci. 2007 Aug;64(16):2153-69. Pubmed

4. Ryanodine receptor 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Ryanodine receptor 1 P21817 Details

References:

  1. Daly JW: Caffeine analogs: biomedical impact. Cell Mol Life Sci. 2007 Aug;64(16):2153-69. Pubmed

5. Cyclic nucleotide phosphodiesterase

Kind: protein group

Organism: Human

Pharmacological action: unknown

Actions: inhibitor, competitive

Components

Name UniProt ID Details
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A P54750 Details
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B Q01064 Details
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C Q14123 Details
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4A P27815 Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4B Q07343 Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4C Q08493 Details
cAMP-specific 3',5'-cyclic phosphodiesterase 4D Q08499 Details
cAMP-specific 3',5'-cyclic phosphodiesterase 7B Q9NP56 Details
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 Details
cGMP-inhibited 3',5'-cyclic phosphodiesterase A Q14432 Details
cGMP-inhibited 3',5'-cyclic phosphodiesterase B Q13370 Details
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 Details
Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha' P51160 Details
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A Q9HCR9 Details
High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A Q13946 Details
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A O60658 Details
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8B O95263 Details
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 Details
Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha P16499 Details
Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit beta P35913 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
  2. Essayan DM: Cyclic nucleotide phosphodiesterases. J Allergy Clin Immunol. 2001 Nov;108(5):671-80. Pubmed

6. DNA-dependent protein kinase catalytic subunit

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
DNA-dependent protein kinase catalytic subunit P78527 Details

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

7. Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform O00329 Details

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

8. Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform P42336 Details

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

9. Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform P42338 Details

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

10. Inositol 1,4,5-trisphosphate receptor

Kind: protein group

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Inositol 1,4,5-trisphosphate receptor type 1 Q14643 Details
Inositol 1,4,5-trisphosphate receptor type 2 Q14571 Details
Inositol 1,4,5-trisphosphate receptor type 3 Q14573 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

11. Serine-protein kinase ATM

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serine-protein kinase ATM Q13315 Details

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
  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

Enzymes

1. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  3. 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
  4. 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. Epub 2009 Nov 24. Pubmed
  5. 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
  6. Lexicomp

2. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  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
  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. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

4. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

5. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

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
  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. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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
  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. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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
  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. Epub 2009 Nov 24. Pubmed

8. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

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. Epub 2009 Nov 24. Pubmed

9. Cytochrome P450 1B1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1B1 Q16678 Details

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. Epub 2009 Nov 24. Pubmed

10. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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. Epub 2009 Nov 24. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08