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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-trimethylpurine-2,6-dioneNot AvailableNot Available
1,3,7-trimethylxanthineNot AvailableNot Available
7-methyltheophyllineNot AvailableNot Available
Anhydrous caffeineNot AvailableNot Available
CafeínaSpanishNot Available
CaféineFrenchNot Available
CoffeinGermanNot Available
GuaranineNot AvailableNot Available
KoffeinGermanNot Available
MateínaSpanishNot Available
MethyltheobromineNot AvailableNot Available
TheineNot AvailableNot Available
Salts
Name/CAS Structure Properties
Caffeine citrate
Thumb Not applicable DBSALT000866
Brand names
NameCompany
CafcitNot Available
CaffedrineNot Available
DexitacNot Available
DurvitanNot Available
EnerjetsNot Available
No-DozNot Available
Pep-BackNot Available
Quick PepNot Available
VivarinNot 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
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
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
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
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
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
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
Categories
CAS number58-08-2
WeightAverage: 194.1906
Monoisotopic: 194.080375584
Chemical FormulaC8H10N4O2
InChI KeyInChIKey=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
Mass Specshow(8.61 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassImidazopyrimidines
SubclassPurines and Purine Derivatives
Direct parentXanthines
Alternative parentsPurinones; Pyrimidones; N-substituted Imidazoles; Polyamines
Substituentspyrimidone; pyrimidine; n-substituted imidazole; imidazole; azole; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
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
    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
    Property Value Probability
    Human Intestinal Absorption + 0.9974
    Blood Brain Barrier + 0.9935
    Caco-2 permeable + 0.633
    P-glycoprotein substrate Non-substrate 0.7572
    P-glycoprotein inhibitor I Non-inhibitor 0.8086
    P-glycoprotein inhibitor II Non-inhibitor 0.8471
    Renal organic cation transporter Non-inhibitor 0.8872
    CYP450 2C9 substrate Non-substrate 0.7484
    CYP450 2D6 substrate Non-substrate 0.5869
    CYP450 3A4 substrate Non-substrate 0.5305
    CYP450 1A2 substrate Non-inhibitor 0.9046
    CYP450 2C9 substrate Non-inhibitor 0.9906
    CYP450 2D6 substrate Non-inhibitor 0.9836
    CYP450 2C19 substrate Non-inhibitor 0.9927
    CYP450 3A4 substrate Non-inhibitor 0.9618
    CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9924
    Ames test Non AMES toxic 0.9132
    Carcinogenicity Non-carcinogens 0.9359
    Biodegradation Ready biodegradable 0.6696
    Rat acute toxicity 2.9741 LD50, mol/kg Not applicable
    hERG inhibition (predictor I) Weak inhibitor 0.8925
    hERG inhibition (predictor II) Non-inhibitor 0.8702
    Pharmacoeconomics
    Manufacturers
    • Mead johnson and co
    • App pharmaceuticals llc
    • Luitpold pharmaceuticals inc
    • Paddock laboratories inc
    • Sun pharmaceutical industries ltd
    Packagers
    Dosage forms
    FormRouteStrength
    CapsuleOral
    ElixirOral
    LiquidOral
    PillOral
    SolutionOral
    Solution / dropsOral
    SuppositoryRectal
    SuspensionOral
    SyrupOral
    TabletOral
    Tablet, extended releaseOral
    Prices
    Unit descriptionCostUnit
    Migergot 12 2-100 mg Suppository Box105.43USDbox
    Cafcit 20 mg/ml oral soln16.4USDml
    Cafcit 20 mg/ml vial16.4USDml
    Caffeine cit 20 mg/ml oral sol15.21USDml
    Caffeine citrate 20 mg/ml vial12.8USDml
    Migergot suppository7.39USDsuppository
    Esgic tablet2.5USDtablet
    Esgic 50-325-40 mg tablet2.27USDtablet
    Darvon-n 100 mg tablet1.95USDtablet
    Esgic-plus 50-500-40 mg tablet1.95USDtablet
    Cafergot 1-100 mg tablet1.9USDtablet
    Darvon 65 mg pulvule1.49USDeach
    Fioricet 50-325-40 mg tablet1.24USDtablet
    Butalb-apap-caff 50-500-40 tablet1.2USDtablet
    Butalb-apap-caff 50-325-40 tablet0.44USDtablet
    Caffeine citrate powder0.36USDg
    Propoxyphene hcl 65 mg capsule0.33USDcapsule
    Vivarin 200 mg caplet0.17USDcaplet
    Vivarin 200 mg tablet0.17USDtablet
    No doz 200 mg caplet0.16USDcaplet
    Caffeine citrated powder purif0.13USDg
    Stay awake 200 mg tablet0.1USDtablet
    CVS Pharmacy caffeine 200 mg tablet0.09USDtablet
    Ra stay awake 100 mg tablet0.09USDtablet
    Caffeine powder0.07USDg
    Caffeine 200 mg tablet0.01USDtablet
    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 solubility1.10e+01 g/lALOGPS
    logP-0.24ALOGPS
    logP-0.55ChemAxon
    logS-1.2ALOGPS
    pKa (strongest basic)-0.92ChemAxon
    physiological charge0ChemAxon
    hydrogen acceptor count3ChemAxon
    hydrogen donor count0ChemAxon
    polar surface area58.44ChemAxon
    rotatable bond count0ChemAxon
    refractivity49.83ChemAxon
    polarizability18.95ChemAxon
    number of rings2ChemAxon
    bioavailability1ChemAxon
    rule of fiveYesChemAxon
    Ghose filterNoChemAxon
    Veber's ruleNoChemAxon
    MDDR-like ruleNoChemAxon
    Spectra
    Spectra
    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
    ResourceLink
    KEGG DrugD00528
    KEGG CompoundC07481
    PubChem Compound2519
    PubChem Substance46506408
    ChemSpider2424
    BindingDB10849
    ChEBI27732
    ChEMBLCHEMBL113
    Therapeutic Targets DatabaseDAP000099
    PharmGKBPA448710
    IUPHAR407
    Guide to Pharmacology407
    HETCFF
    Drug Product Database2241831
    RxListhttp://www.rxlist.com/cgi/generic3/caffeine.htm
    Drugs.comhttp://www.drugs.com/caffeine.html
    WikipediaCaffeine
    ATC CodesN06BC01N02BE01
    AHFS Codes
    • 28:20.92
    • 28:08.92
    • 92:02.00*
    • 28:20.00
    PDB EntriesNot Available
    FDA labelshow(37.7 KB)
    MSDSshow(76.1 KB)
    Interactions
    Drug Interactions
    Drug
    AdenosineCaffeine may diminish the therapeutic effect of adenosine. Specific management recommendations vary slightly depending on specific adenosine product used (i.e., therapeutic vs. diagnostic use of adenosine). Significantly higher adenosine doses, or alternative agents, may be required. Monitor for decreased therapeutic effects of adenosine if the patient is already receiving caffeine. Discontinue caffeine in advance (5 half-lives, or approximately 24 hours, is specifically recommended) of scheduled diagnostic use of adenosine (e.g., for radionuclide imaging studies) whenever possible.
    CiprofloxacinCiprofloxacin may increase the effect and toxicity of caffeine.
    ClozapineCaffeine increases the effect and toxicity of clozapine
    ConivaptanConivaptan may increase the serum concentration of CYP3A4 substrates such as caffeine. Upon completion/discontinuation of conivaptan, allow at least 7 days before initiating therapy with drugs that are CYP3A4 substrates.
    GrepafloxacinGrepafloxacin may increase the effect and toxicity of caffeine.
    LithiumCaffeine decreases serum levels of lithium
    NorfloxacinNorfloxacin may increase the effect and toxicity of caffeine.
    RegadenosonCaffeine may diminish the vasodilatory effect of Regadenoson. Regadenoson prescribing information recommends avoiding using caffeine or other methylxanthine containing products (e.g., theophylline) for at least 12 hours prior the the administration of regadenoson. The impact of low doses of caffeine-containing products such as coffee, tea, and colas is unclear.
    TamsulosinCaffeine, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Caffeine is initiated, discontinued, or dose changed.
    TerbinafineTerbinafine may increase the plasma concentration of Caffeine.
    ThiabendazoleThe strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Caffeine by decreasing Caffeine metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Caffeine if Thiabendazole is initiated, discontinued or dose changed.
    TolterodineCaffeine may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
    VemurafenibVemurafenib increases the AUC of caffeine (CYP1A2 substrate) 2.6-fold.
    Food InteractionsNot Available

    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

    1. 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.

    2. 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

    3. 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.

    4. 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

    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

    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

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