Identification

Name
Caffeine
Accession Number
DB00201  (APRD00673)
Type
Small Molecule
Groups
Approved
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 Key
Caffeine citrateU26EO4675Q69-22-7RCQXSQPPHJPGOF-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CafcitSolution20 mg/1mLOralBedford Pharmaceuticals2008-11-042016-05-29Us
CafcitInjection20 mg/1mLIntravenousBedford Pharmaceuticals2008-11-042016-04-30Us
CafcitInjection20 mg/1mLIntravenousWest Ward Pharmaceutical2008-11-04Not applicableUs
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
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Caffeine CitrateInjection20 mg/1mLIntravenousSun Pharmaceutical Industries, Inc.2009-10-01Not applicableUs
Caffeine CitrateInjection20 mg/1mLIntravenousExela Pharma Sciences, Llc.2006-09-21Not applicableUs
Caffeine CitrateInjection20 mg/1mLIntravenousSun Pharmaceutical Industries Ltd2009-10-01Not applicableUs
Caffeine CitrateInjection, solution60 mg/3mLIntramuscular; IntravenousMicro Labs Limited2017-12-30Not applicableUs
Caffeine CitrateSolution20 mg/1mLOralRemedy Repack2013-10-312014-10-31Us
Caffeine CitrateSolution20 mg/1mLOralExela Pharma Sciences, Llc.2006-09-21Not applicableUs
Caffeine CitrateSolution20 mg/1mLOralSagent Pharmaceuticals2012-09-15Not applicableUs
Caffeine CitrateInjection, solution20 mg/1mLIntravenousAMERICAN REGENT, INC.2007-09-10Not applicableUs
Caffeine CitrateSolution20 mg/1mLOralAPP Pharmaceuticals, Inc.2009-11-19Not applicableUs
Caffeine CitrateInjection20 mg/1mLIntravenousExela Pharma Sciences, Llc.2006-09-21Not applicableUs
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/1OralDOLGENCORP, LLC1996-11-21Not applicableUs
Alert AidTablet200 mg/1OralAmerisource Bergen1996-11-21Not 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.1996-11-21Not applicableUs
Alert Tab 100mgTablet100 mgOralNutribon (1986) Inc.1995-12-311996-09-30Canada
Alertness AidTablet200 mg/1OralCardinal Health1996-11-21Not applicableUs
Alertness AidTablet200 mg/1OralChain Drug Consortium1996-11-21Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
(extra Strength) Acetaminophen, Caffeine & 8mg Codeine Phosphate CapletsCaffeine (15 mg) + Acetaminophen (500 mg) + Codeine phosphate (8 mg)TabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1998-07-222002-07-31Canada
217Caffeine citrate (30 mg) + Acetylsalicylic acid (325 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1910-12-311998-04-21Canada
217 Strong TabCaffeine citrate (30 mg) + Acetylsalicylic acid (500 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1973-12-311998-04-21Canada
222 TabletsCaffeine citrate (30 mg) + Acetylsalicylic acid (375 mg) + Codeine phosphate (8 mg)TabletOralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1951-12-312015-08-17Canada
282 Mep TabCaffeine citrate (30 mg) + Acetylsalicylic acid (350 mg) + Codeine phosphate (15 mg) + Meprobamate (200 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1959-12-311998-08-14Canada
282 TabCaffeine citrate (30 mg) + Acetylsalicylic acid (375 mg) + Codeine phosphate (15 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1951-12-311998-04-21Canada
282 TabletsCaffeine citrate (30 mg) + Acetylsalicylic acid (375 mg) + Codeine phosphate (15 mg)TabletOralPendopharm Division Of De Pharmascience Inc1998-11-01Not applicableCanada
292 TabCaffeine citrate (30 mg) + Acetylsalicylic acid (375 mg) + Codeine phosphate (30 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1951-12-311998-08-14Canada
292 TabletsCaffeine citrate (30 mg) + Acetylsalicylic acid (375 mg) + Codeine phosphate (30 mg)TabletOralPendopharm Division Of De Pharmascience Inc1998-10-01Not applicableCanada
692 TabCaffeine (30 mg) + Acetylsalicylic acid (375 mg) + Dextropropoxyphene hydrochloride (65 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1986-02-131998-04-21Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Caffeine and Sodium BenzoateCaffeine (125 mg/1mL)Injection, solutionIntramuscular; IntravenousAmerican Regent1993-02-01Not applicableUs
Isometheptene Mucate, Caffeine, AcetaminophenCaffeine (100 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1)CapsuleOralRiver's Edge Pharmaceuticals, LLC2008-07-012010-09-30Us
Isometheptene Mucate, Caffeine, and AcetaminophenCaffeine (20 mg/1) + Acetaminophen (500 mg/1) + Isometheptene mucate (130 mg/1)TabletOralWomens Choice Pharmaceuticals, Llc2011-10-122014-01-14Us
Isometheptene Mucate, Caffeine, and AcetaminophenCaffeine (20 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1)TabletOralBurel Pharmaceuticals, Llc2016-04-172017-04-30Us
Isometheptene Mucate, Caffeine, and AcetaminophenCaffeine (20 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1)TabletOralXspire Pharma2010-06-012018-01-15Us
MigraTenCaffeine (100 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1)CapsuleOralAzur Pharma, Inc.2005-01-012010-06-01Us
ProdrinCaffeine (20 mg/1) + Acetaminophen (325 mg/1) + Isometheptene mucate (65 mg/1)TabletOralGentex Pharma2010-06-012018-01-15Us
International/Other Brands
Caffedrine / Dexitac / Durvitan / Enerjets / No-Doz / Pep-Back / Quick Pep / Wake-Up
Categories
UNII
3G6A5W338E
CAS number
58-08-2
Weight
Average: 194.1906
Monoisotopic: 194.080375584
Chemical Formula
C8H10N4O2
InChI Key
RYYVLZVUVIJVGH-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.

Associated Conditions
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.

TargetActionsOrganism
AAdenosine receptor A1
antagonist
multitarget
Human
AAdenosine receptor A2a
antagonist
multitarget
Human
UcAMP-specific 3',5'-cyclic phosphodiesterase 4B
inhibitor
Human
URyanodine receptor 1Not AvailableHuman
UCyclic nucleotide phosphodiesterase
inhibitor
Human
UDNA-dependent protein kinase catalytic subunit
inhibitor
Human
UPhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
inhibitor
Human
UPhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
inhibitor
Human
UPhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform
inhibitor
Human
UInositol 1,4,5-trisphosphate receptor
inhibitor
Human
USerine-protein kinase ATM
inhibitor
Human
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).

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

Clearance
Not Available
Toxicity

LD50=127 mg/kg (orally in mice)

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Caffeine MetabolismMetabolic
Caffeine MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 1A2---(A;C) / (C;C)C alleleADR Directly StudiedPatients with this genotype have increased risk of a non-fatal myocardial infarction with caffeineDetails

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe serum concentration of Caffeine can be increased when it is combined with (R)-warfarin.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Caffeine.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Caffeine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Caffeine.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Caffeine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Caffeine.
3,5-diiodothyropropionic acidThe serum concentration of Caffeine can be increased when it is combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Caffeine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Caffeine.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Caffeine.
Food Interactions
Not 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
Human Metabolome Database
HMDB0001847
KEGG Drug
D00528
KEGG Compound
C07481
PubChem Compound
2519
PubChem Substance
46506408
ChemSpider
2424
BindingDB
10849
ChEBI
27732
ChEMBL
CHEMBL113
Therapeutic Targets Database
DAP000099
PharmGKB
PA448710
IUPHAR
407
Guide to Pharmacology
GtP Drug Page
HET
CFF
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Caffeine
ATC Codes
V04CG30 — Caffeine and sodium benzoateR03DA20 — Combinations of xanthinesN06BC01 — Caffeine
AHFS Codes
  • 28:20.00 — Anorexigenic Agents & Respiratory and CNS Stimulants
  • 28:20.32 — Respiratory and CNS Stimulants
PDB Entries
1c8l / 1gfz / 1l5q / 1l7x / 2a3b / 3dd1 / 3dds / 3ddw / 3g6m / 3rfm
show 13 more
FDA label
Download (37.7 KB)
MSDS
Download (76.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceHealthy Volunteers1
0CompletedBasic ScienceVoice Disorders1
0CompletedTreatmentType 2 Diabetes Mellitus1
0RecruitingTreatmentPostoperative pain1
0Unknown StatusBasic SciencePsychotropic Drugs Effects1
1Active Not RecruitingBasic ScienceNash1
1Active Not RecruitingBasic ScienceNeoplasms Metastasis1
1Active Not RecruitingOtherNeoplasms1
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailablePain, Chronic1
1CompletedBasic ScienceAlzheimer's Disease (AD) / Metabolism1
1CompletedBasic ScienceAtopic Dermatitis (AD)1
1CompletedBasic ScienceDrug Biotransformation / Membrane Transport1
1CompletedBasic ScienceDrug Drug Interaction (DDI)1
1CompletedBasic ScienceHealthy Volunteers3
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics of Caffeine / Pharmacokinetics of Repaglinide1
1CompletedBasic SciencePharmacokinetics of Caffeine / Pharmacokinetics of Dextromethorphan / Prostate Cancer1
1CompletedBasic ScienceRheumatoid Arthritis1
1CompletedDiagnosticCytochrome / Pharmacokinetics1
1CompletedDiagnosticDrug Drug Interaction (DDI)1
1CompletedDiagnosticHealthy Volunteers1
1CompletedDiagnosticMolecular Imaging / Molecular Imaging [E01.370.350.557]1
1CompletedHealth Services ResearchCognitively Healthy Subjects Influenced by Psychoactive Drugs1
1CompletedHealth Services ResearchHealthy Volunteers1
1CompletedOtherHealthy Volunteers / Rheumatoid Arthritis1
1CompletedOtherTumors, Solid1
1CompletedPreventionEndotoxaemia1
1CompletedTreatmentAdvanced Solid Tumors, Excluding Breast Cancer1
1CompletedTreatmentAnemias / Healthy Volunteers1
1CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
1CompletedTreatmentCompulsive Behavior / Substance Dependence1
1CompletedTreatmentDrug Drug Interaction (DDI)2
1CompletedTreatmentHealthy Volunteers9
1CompletedTreatmentInfectious Diseases1
1CompletedTreatmentPsoriasis2
1CompletedTreatmentCMET-dysregulated Advanced Solid Tumors1
1RecruitingOtherCrohn's Disease (CD)1
1RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1RecruitingTreatmentAtopic Dermatitis (AD)1
1RecruitingTreatmentTumors, Solid1
1Unknown StatusBasic ScienceHealthy Volunteers2
1WithdrawnBasic ScienceLiver Diseases1
1, 2CompletedBasic ScienceDependence, Cocaine1
1, 2RecruitingSupportive CareNarcolepsy1
1, 2WithdrawnTreatmentAmblyopia1
2CompletedPreventionAdenoidectomy / Postoperative Complications / Sleep Apnea, Obstructive / Tonsillectomy1
2CompletedPreventionRetinopathy of Prematurity1
2CompletedSupportive CareMalignancies / Pain NOS1
2CompletedTreatmentBMI >30 kg/m21
2CompletedTreatmentParkinson's Disease (PD)1
2Not Yet RecruitingTreatmentApnea1
2Not Yet RecruitingTreatmentIntermittent Hypoxia1
2RecruitingTreatmentPostoperative paralytic ileus1
2TerminatedTreatmentDyspnea1
2, 3CompletedTreatmentCocaine Related Disorders1
2, 3CompletedTreatmentExcessive Daytime Somnolence / Parkinson's Disease (PD)1
2, 3RecruitingTreatmentCaffeine Withdrawal / Migraines1
2, 3RecruitingTreatmentCaffeine / Cellulitis1
3CompletedNot AvailableMyocardial Infarction1
3CompletedBasic ScienceBMI >30 kg/m21
3CompletedPreventionApnea / Preterm, Infant1
3CompletedPreventionCoronary Heart Disease (CHD)1
3CompletedPreventionPrimary apnea of premature newborns1
3CompletedTreatmentBack Pain / Cervical Pain1
3CompletedTreatmentDysmenorrhea1
3CompletedTreatmentIntermittent Claudication1
3CompletedTreatmentMigraine Disorders1
3CompletedTreatmentPain NOS2
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 RecruitingTreatmentPrimary apnea of premature newborns1
3Unknown StatusTreatmentHeadaches1
3WithdrawnTreatmentPain NOS1
4CompletedBasic ScienceFeeling Anxious1
4CompletedBasic ScienceRejection, Transplant1
4CompletedPreventionAnaesthesia therapy1
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 / Lung Cancer Non-Small Cell Cancer (NSCLC) / Renal-cell Cancer1
4CompletedTreatmentHealthy Elderly Citizens1
4CompletedTreatmentPain, Migraine1
4CompletedTreatmentAcute Rhinitis1
4Not Yet RecruitingBasic ScienceAdult Population1
4Not Yet RecruitingPreventionAnaesthesia therapy1
4RecruitingBasic ScienceType 2 Diabetes Mellitus1
4RecruitingPreventionBPD - Bronchopulmonary Dysplasia / Hemodynamics Instability / Intubations / Primary apnea of premature newborns1
4RecruitingTreatmentCrohn's Disease (CD) / Ulcerative Colitis (UC)1
4SuspendedNot AvailableLabor, First Stage1
4TerminatedOtherPain NOS1
4TerminatedTreatmentMigrainous Headache1
4Unknown StatusScreeningHealthy Volunteers1
4Unknown StatusTreatmentDependence, Cocaine1
Not AvailableActive Not RecruitingNot AvailableAutonomic Nervous System / Cardiorespiratory Parameters1
Not AvailableActive Not RecruitingScreeningAlcohol Dependence1
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 AvailableCaffeine / Premature Newborns / Primary apnea of premature newborns1
Not AvailableCompletedNot AvailableDrug Half Life / Pharmacokinetics / Placebo Effect1
Not AvailableCompletedNot AvailableGrowth Hormone Deficiency, Dwarfism1
Not AvailableCompletedNot AvailableHealthy Volunteers / High Blood Pressure (Hypertension)1
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Eating Behavior1
Not AvailableCompletedBasic ScienceDrug Drug Interaction (DDI) / Healthy Volunteers1
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 AvailableCompletedPreventionPost-Operative Nausea and Vomiting (PONV)1
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 AvailableDepression1
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 / Infants, Premature / 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
  • Actavis Group
  • Aidarex Pharmacuticals LLC
  • Alphagen Laboratories Inc.
  • American Regent
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotheca Inc.
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • Athlon Pharmaceuticals Inc.
  • Atley Pharmaceuticals
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bioniche Pharma
  • Blansett Pharmacal Co. Inc.
  • Blenheim Pharmacal
  • Brighton Pharmaceuticals
  • Bristol-Myers Squibb Co.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Comprehensive Consultant Services Inc.
  • Concord Labs
  • Corepharma LLC
  • CVS Pharmacy
  • D.M. Graham Laboratories Inc.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Everett Laboratories Inc.
  • Forest Pharmaceuticals
  • G & W Labs
  • Gilbert Laboratories
  • GlaxoSmithKline Inc.
  • Goldline Laboratories Inc.
  • Heartland Repack Services LLC
  • Hope Pharmaceuticals
  • Hospira Inc.
  • Innoviant Pharmacy Inc.
  • J T Baker
  • Kaiser Foundation Hospital
  • Keene Pharmaceuticals Inc.
  • Keltman Pharmaceuticals Inc.
  • Lannett Co. Inc.
  • Liberty Pharmaceuticals
  • Luitpold Pharmaceuticals Inc.
  • Lunsco Inc.
  • Major Pharmaceuticals
  • Mallinckrodt Inc.
  • Marlex Pharmaceuticals
  • Marnel Pharmaceuticals Inc.
  • MCR American Pharmaceuticals Inc.
  • Mikart Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nexgen Pharma Inc.
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Paddock Labs
  • Palmetto Pharmaceuticals Inc.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Poly Pharmaceuticals Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Prometic Pharma Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Resource Optimization and Innovation LLC
  • Rising Pharmaceuticals
  • Rite Aid Corp.
  • Sandhills Packaging Inc.
  • Sciele Pharma Inc.
  • Seatrace Pharmaceuticals Inc.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Talbert Medical Management Corp.
  • Teva Pharmaceutical Industries Ltd.
  • US Pharmaceutical Corp.
  • Va Cmop Dallas
  • Victory Pharma
  • Vintage Pharmaceuticals Inc.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
  • Xanodyne Pharmaceuticals Inc.
Dosage forms
FormRouteStrength
Tablet, multilayerOral200 1/1
CapsuleOral175 mg
TabletOral175 mg
TabletOral100 mg
Tablet, effervescentOral
Tablet, coatedOral
SyrupOral
SuppositoryRectal
Tablet, multilayerOral200 mg/200mg
Injection, solutionIntramuscular; Intravenous125 mg/1mL
InjectionIntravenous20 mg/1mL
Injection, solutionIntramuscular; Intravenous60 mg/3mL
Injection, solutionIntravenous20 mg/1mL
SolutionIntravenous20 mg/1mL
SolutionOral20 mg/1mL
CapsuleOral
TabletOral200 mg
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral200 mg/1
Kit
Tablet, film coatedOral
Capsule, gelatin coatedOral
SolutionOral
GranuleOral
Capsule, coatedOral
TabletTopical
PowderOral
TabletOral200 mg/1
Tablet, coatedOral100 mg/1
Capsule, liquid filledOral200 mg/1
Capsule, liquid filledOral
CreamTopical
CreamTopical5.0 mg/1000mL
Tablet, multilayerOral
Injection, solution; solutionIntravenous; Oral20 mg/ml
CapsuleOral100 mg
PowderTopical
LiquidOral
LozengeOral50 mg/1
WaferOral60 mg
Tablet, coatedOral200 mg/1
LiquidOral50 mg
TabletOral
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)
US5972916No1999-10-262017-07-14Us

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)GC-MSsplash10-0536-3900000000-a9e112713ffae6dabdaa
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)GC-MSsplash10-0536-2900000000-8cdcd005b2e7622a02a3
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-052f-0900000000-f1084acfddb240696073
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-05nf-6900000000-8670a644cee5d9de78d4
GC-MS Spectrum - GC-MSGC-MSsplash10-0536-3900000000-4430852b279a72e34822
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0006-0900000000-51898e93480e848d7da1
GC-MS Spectrum - CI-BGC-MSsplash10-0002-0900000000-2aed5d425b6a95add5db
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-4900000000-3ff72dace6687d242f1f
GC-MS Spectrum - EI-BGC-MSsplash10-0006-1900000000-2ba1fae6e27c7b836984
GC-MS Spectrum - CI-BGC-MSsplash10-0002-0900000000-fd859aeb416e320d6379
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0536-3900000000-a9e112713ffae6dabdaa
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0536-2900000000-8cdcd005b2e7622a02a3
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-052f-0900000000-f1084acfddb240696073
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-05nf-6900000000-8670a644cee5d9de78d4
GC-MS Spectrum - GC-MSGC-MSsplash10-0536-3900000000-4430852b279a72e34822
Mass Spectrum (Electron Ionization)MSsplash10-052f-8900000000-68b5e9aa3404fb3d8d3a
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0006-0900000000-447fc72b2c709e2e18a9
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-000i-1900000000-5e3b29de16ad91c79fe0
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0006-9100000000-d6f6c52ac36c8f25a500
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-0006-0900000000-cddd24399d942b1ac97c
MS/MS Spectrum - CI-B (Unknown) , PositiveLC-MS/MSsplash10-0002-0900000000-2aed5d425b6a95add5db
MS/MS Spectrum - EI-B (HITACHI M-60) , PositiveLC-MS/MSsplash10-0a4l-4900000000-3ff72dace6687d242f1f
MS/MS Spectrum - EI-B (HITACHI M-68) , PositiveLC-MS/MSsplash10-0006-1900000000-2ba1fae6e27c7b836984
MS/MS Spectrum - CI-B (HITACHI M-60) , PositiveLC-MS/MSsplash10-0002-0900000000-63b9ef42a3e8d59e9997
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0002-0900000000-185b3d97d8857a0f269d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0002-0900000000-f8a0c0dd9f5c4a272eaf
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-000i-1900000000-dd8e35226d0704aa657d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-01x9-9800000000-70e3b0eb52481c39d191
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-001l-9100000000-6d428a5571beb0e3fed4
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0002-0900000000-98bec16f898808c3de68
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-0002-0900000000-b112e4e059e1ecf98c5f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-761710441aa2c1c3ac68
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000b-0900000000-c10af6eda9a9a4094715
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01p9-3900000000-141118b1a93b4d48b2d4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-c8bd8cccb7dd6c66bb42
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-2c8c1760161edd358026
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-5900000000-260de4a79007e853e4bb
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-695d910d49fc0beb1d54
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-094879886a2e72bf0c56
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-fa38c865089a3a05f287
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000b-0900000000-0e82732a924c974dd0c8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-bfc94c8091471847482b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-1900000000-c8fcf16986c494898203
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-3900000000-9569e0552abb7ebd145a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-3a924abd44877050c1c9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-c6803f746febffe7ab6b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-66e04d2c507b4751e506
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-9af60e39c843cb715435
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-1900000000-f858247f1e9a9dc03988
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-3900000000-73043667076aaf483c6e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-2175b91e18c95954cc54
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-013ba6bf69c2800dafeb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000b-0900000000-1ad354a17e0fd85a18db
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-f751c01e71d548d07cfa
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01w0-0900000000-88cd919e5f37c53adf12
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-807dd2315cef11dedba7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-2900000000-87822a5f5a6be99a2eaa
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-5900000000-6f909aa0d652aca47648
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9500000000-e06eca9e3e2ab56477d0
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0002-0900000000-1c1dcfab5dc129669de4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0002-0900000000-fe8fd0aa7989e70bba69
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-1900000000-dd8e35226d0704aa657d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01x9-9800000000-9e04f1fb471150acc039
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001l-9100000000-6d428a5571beb0e3fed4
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-0900000000-c32a8e70a7c0e7c6b19b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-98bec16f898808c3de68
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-b112e4e059e1ecf98c5f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000j-0900000000-fb4fdea2278a980eebd9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-d625aea76a3256436c31
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-6cd84afa1441c734413d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-bc9f9a43b0fd465d435c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-413259091ba7edc46b87
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-b8ca373712477994b200
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-5e7721bcb84a3ae2c1eb
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-64da1f31ba17e532a3c6
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-6f74190396d61622726f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-238b01405bce15c86f0d
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-4900000000-a60a480f1340558740a2
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0900000000-3b056c4352ea9d7dcd81
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000j-0900000000-409abf86df5de9a03860
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-f236794b68cee8f6798c
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-3d4e16572c9b12ac6836
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-ac06ecf59a06be305ff0
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Xanthines
Alternative Parents
6-oxopurines / Alkaloids and derivatives / Pyrimidones / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Xanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Pyrimidone / N-substituted imidazole / Pyrimidine / Azole / Imidazole / Heteroaromatic compound
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
purine alkaloid, trimethylxanthine (CHEBI:27732) / Purine alkaloids (C07481) / a small molecule (1-3-7-TRIMETHYLXANTHINE)

Targets

Details
1. Adenosine receptor A1
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
Multitarget
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]
Details
2. Adenosine receptor A2a
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
Multitarget
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 f...
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-tu...
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
Actions
Inhibitor
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 cG...

Components:
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
Actions
Inhibitor
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 recombinati...
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
Actions
Inhibitor
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 rec...
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
Actions
Inhibitor
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...
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
Actions
Inhibitor
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...
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
Actions
Inhibitor
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 elect...

Components:
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
Actions
Inhibitor
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...
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
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 un...
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
Inhibitor
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 un...
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. Hartter S, Nordmark A, Rose DM, Bertilsson L, Tybring G, Laine K: Effects of caffeine intake on the pharmacokinetics of melatonin, a probe drug for CYP1A2 activity. Br J Clin Pharmacol. 2003 Dec;56(6):679-82. [PubMed:14616429]
  6. 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 un...
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
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 react...
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
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 ...
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 un...
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 un...
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]
  3. Utoh M, Murayama N, Uno Y, Onose Y, Hosaka S, Fujino H, Shimizu M, Iwasaki K, Yamazaki H: Monkey liver cytochrome P450 2C9 is involved in caffeine 7-N-demethylation to form theophylline. Xenobiotica. 2013 Dec;43(12):1037-42. doi: 10.3109/00498254.2013.793874. Epub 2013 May 16. [PubMed:23679834]
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 un...
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 un...
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...
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]
  2. Ha HR, Chen J, Krahenbuhl S, Follath F: Biotransformation of caffeine by cDNA-expressed human cytochromes P-450. Eur J Clin Pharmacol. 1996;49(4):309-15. [PubMed:8857078]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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 November 20, 2018 13:19