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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. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Cafeina
Caffein
CFF
Methyltheobromide
Methyltheobromine
Theobromine ME
Theophylline ME
Salts Not Available
Brand names
Name Company
Alert-Pep
Cafamil
Cafcit
Cafecon
Caffedrine
Caffine
Cafipel
Coffein
Coffeine
Dasin
Dexitac
DHC Plus
Diurex
Durvitan
Eldiatric C
Enerjets
Ercatab
Fioricet
Guaranine
Hycomine
Keep Alert
Kofein
Koffein
Mateina
Miudol
Nix Nap
No-Doz
Nodaca
Norgesic Forte
Organex
Pep-Back
Phensal
Quick Pep
Refresh'n
Stim
Thein
Theine
Vivarin
Wake-Up
Wigraine
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Brand mixtures
Brand Name Ingredients
A & C Tablets with Codeine Acetylsalicylic Acid + Caffeine + Codeine Phosphate
AC&C Acetylsalicylic Acid + Caffeine + Codeine Phosphate
Acet 2 Acetaminophen + Caffeine + Codeine Phosphate
Acet 3 Acetaminophen + Caffeine + Codeine Phosphate
Alka-Seltzer Morning Relief Acetylsalicylic Acid + Caffeine
Anacin Acetylsalicylic Acid + Caffeine
Antidol Acetylsalicylic Acid + Caffeine
Arco Pain Tab Acetylsalicylic Acid + Caffeine Citrate
Astone Cap Acetylsalicylic Acid + Caffeine
Atasol Acetaminophen + Caffeine Citrate + Codeine Phosphate
Cafergot Caffeine + Ergotamine Tartrate
Cafergot PB Belladonna + Caffeine + Ergotamine (Ergotamine Tartrate) + Pentobarbital
Calmine Acetylsalicylic Acid + Caffeine
Codaminophen Acetaminophen + Caffeine + Codeine Phosphate
Corytab Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride
Cotabs Acetaminophen + Caffeine Citrate + Codeine Phosphate
Darvon N Compound Pulvule 405 Acetylsalicylic Acid + Caffeine + Dextropropoxyphene Napsylate
Dolomine 37 Acetylsalicylic Acid + Caffeine
Dristan Acetylsalicylic Acid + Caffeine + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride
Emercidin D Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
Emertabs Acetaminophen + Caffeine + Phenylpropanolamine Hydrochloride
Ergodryl Caffeine Citrate + Diphenhydramine Hydrochloride + Ergotamine Tartrate
Excedrin Acetaminophen + Caffeine
Exdol Acetaminophen + Caffeine Citrate + Codeine Phosphate
Fiorinal Acetylsalicylic Acid + Butalbital + Caffeine + Codeine Phosphate
Gravergol Caffeine + Dimenhydrinate + Ergotamine Tartrate
Herbopyrine Acetylsalicylic Acid + Caffeine Citrate
Instantine Acetylsalicylic Acid + Caffeine
Invagesic caffeine + salicylic acid + orphenadrine
Madelon Acetylsalicylic Acid + Caffeine
Megral Caffeine + Cyclizine Hydrochloride + Ergotamine Tartrate
Midol Acetylsalicylic Acid + Caffeine + Cinnamedrine
Neo Tigol Acetylsalicylic Acid + Aluminum Hydroxide + Caffeine + Magnesium Hydroxide + Passion Flower + Valerian
Nervine Acetylsalicylic Acid + Caffeine
Norgesic Acetylsalicylic Acid + Caffeine + Orphenadrine Citrate
Novo AC and C Acetylsalicylic Acid + Caffeine + Codeine Phosphate
Novo-Gesic Acetaminophen + Caffeine + Codeine Phosphate
Novo-Propoxyn Compound Acetylsalicylic Acid + Caffeine + Dextropropoxyphene Hydrochloride
Oradrine 2 Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
Pain Aid Acetylsalicylic Acid + Caffeine
Painex Acetylsalicylic Acid + Caffeine Citrate + Codeine Phosphate
Ratio-Lenoltec No 1 Acetaminophen + Caffeine + Codeine Phosphate
Ratio-Lenoltec No 2 Acetaminophen + Caffeine + Codeine Phosphate
Ratio-Lenoltec No 3 Acetaminophen + Caffeine + Codeine Phosphate
Ratio-Tecnal Acetylsalicylic Acid + Butalbital + Caffeine
Sinugex 38 Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride
Triaminicin Colds & Flu Acetaminophen + Caffeine + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Trianal Acetylsalicylic Acid + Butalbital + Caffeine
Triatec-8 Fort Acetaminophen + Caffeine Citrate + Codeine Phosphate
Tylenol No 1 Acetaminophen + Caffeine + Codeine Phosphate
Tylenol No.1 Forte Acetaminophen + Caffeine + Codeine Phosphate
Tylenol No1 Forte Tablets with Codeine Acetaminophen + Caffeine + Codeine Phosphate
Tylenol Ultra Relief Acetaminophen + Caffeine
Tylenol with Codeine No. 2 Acetaminophen + Caffeine + Codeine Phosphate
Tylenol with Codeine No. 3 Acetaminophen + Caffeine + Codeine Phosphate
Ultra Headache Relief Acetaminophen + Caffeine
Wigraine Belladonna + Caffeine + Ergotamine Tartrate
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Categories
  • Central Nervous System Stimulants
  • Anorexigenic Agents
  • Phosphodiesterase Inhibitors
CAS number 58-08-2
Weight Average: 194.1906
Monoisotopic: 194.080375584
Chemical Formula C8H10N4O2
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec show (8.61 KB)
Taxonomy
Kingdom Organic
Classes
  • Xanthines
Substructures
  • Xanthines
  • Pyrimidines and Derivatives
  • Imidazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Purines and Purine Derivatives
  • Cyanamides
Pharmacology
Indication For management of fatigue, orthostatic hypotension, and for the short term treatment of apnea of prematurity in infants.
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.
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 Not Available
Pharmacoeconomics
Manufacturers
  • Mead johnson and co
  • App pharmaceuticals llc
  • Luitpold pharmaceuticals inc
  • Paddock laboratories inc
  • Sun pharmaceutical industries ltd
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Elixir Oral
Liquid Oral
Pill Oral
Solution Oral
Solution / drops Oral
Suppository Rectal
Suspension Oral
Syrup Oral
Tablet Oral
Tablet, extended release Oral
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Prices
Unit description Cost Unit
Migergot 12 2-100 mg Suppository Box 105.43 USD box
Cafcit 20 mg/ml oral soln 16.4 USD ml
Cafcit 20 mg/ml vial 16.4 USD ml
Caffeine cit 20 mg/ml oral sol 15.21 USD ml
Caffeine citrate 20 mg/ml vial 12.8 USD ml
Migergot suppository 7.39 USD suppository
Esgic tablet 2.5 USD tablet
Esgic 50-325-40 mg tablet 2.27 USD tablet
Darvon-n 100 mg tablet 1.95 USD tablet
Esgic-plus 50-500-40 mg tablet 1.95 USD tablet
Cafergot 1-100 mg tablet 1.9 USD tablet
Darvon 65 mg pulvule 1.49 USD each
Fioricet 50-325-40 mg tablet 1.24 USD tablet
Butalb-apap-caff 50-500-40 tablet 1.2 USD tablet
Butalb-apap-caff 50-325-40 tablet 0.44 USD tablet
Caffeine citrate powder 0.36 USD g
Propoxyphene hcl 65 mg capsule 0.33 USD capsule
Vivarin 200 mg caplet 0.17 USD caplet
Vivarin 200 mg tablet 0.17 USD tablet
No doz 200 mg caplet 0.16 USD caplet
Caffeine citrated powder purif 0.13 USD g
Stay awake 200 mg tablet 0.1 USD tablet
CVS Pharmacy caffeine 200 mg tablet 0.09 USD tablet
Ra stay awake 100 mg tablet 0.09 USD tablet
Caffeine powder 0.07 USD g
Caffeine 200 mg tablet 0.01 USD tablet
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 238 °C PhysProp
water solubility 2.16E+004 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP -0.07 HANSCH,C ET AL. (1995)
logS -0.97 ADME Research, USCD
Caco2 permeability -4.41 ADME Research, USCD
pKa 10.4 (at 40 °C) DEAN,JA (1985)
Predicted Properties
Property Value Source
water solubility 1.10e+01 g/l ALOGPS
logP -0.24 ALOGPS
logP -0.55 ChemAxon
logS -1.2 ALOGPS
pKa (strongest basic) -0.92 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 58.44 ChemAxon
rotatable bond count 0 ChemAxon
refractivity 49.83 ChemAxon
polarizability 18.95 ChemAxon
References
Synthesis Reference Not Available
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
Resource Link
KEGG Drug D00528 Link_out
KEGG Compound C07481 Link_out
PubChem Compound 2519 Link_out
PubChem Substance 46506408 Link_out
ChemSpider 2424 Link_out
BindingDB 10849 Link_out
ChEBI 27732 Link_out
ChEMBL 27732 Link_out
Therapeutic Targets Database DAP000099 Link_out
PharmGKB PA448710 Link_out
IUPHAR 407 Link_out
Guide to Pharmacology 407 Link_out
HET CFF Link_out
Drug Product Database 2241831 Link_out
RxList http://www.rxlist.com/cgi/generic3/caffeine.htm Link_out
Drugs.com http://www.drugs.com/caffeine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Caffeine Link_out
ATC Codes
  • N06BC01
  • N02BE01
AHFS Codes
  • 28:20.92
  • 28:08.92
  • 92:02.00*
  • 28:20.00
PDB Entries Not Available
FDA label show (37.7 KB)
MSDS show (76.1 KB)
Interactions
Drug Interactions
Drug Interaction
Adenosine Caffeine 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.
Ciprofloxacin Ciprofloxacin may increase the effect and toxicity of caffeine.
Clozapine Caffeine increases the effect and toxicity of clozapine
Conivaptan Conivaptan 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.
Grepafloxacin Grepafloxacin may increase the effect and toxicity of caffeine.
Lithium Caffeine decreases serum levels of lithium
Norfloxacin Norfloxacin may increase the effect and toxicity of caffeine.
Regadenoson Caffeine 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.
Tamsulosin Caffeine, 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.
Terbinafine Terbinafine may increase the plasma concentration of Caffeine.
Thiabendazole The 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.
Tolterodine Caffeine may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Vemurafenib Vemurafenib increases the AUC of caffeine (CYP1A2 substrate) 2.6-fold.
Food Interactions Not Available
Targets

1. Adenosine A1 receptor

Pharmacological action: yes
Actions: antagonist, multitarget

Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase

Organism class: human
UniProt ID: P30542 Link_out
Gene: ADORA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 A2a receptor

Pharmacological action: yes
Actions: antagonist, multitarget

Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase

Organism class: human
UniProt ID: P29274 Link_out
Gene: ADORA2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: inhibitor

May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents

Organism class: human
UniProt ID: Q07343 Link_out
Gene: PDE4B Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown

Communication between transverse-tubules and sarcoplasmic reticulum. Contraction of skeletal muscle is triggered by release of calcium ions from SR following depolarization of T-tubules

Organism class: human
UniProt ID: P21817 Link_out
Gene: RYR1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

1. Cytochrome P450 3A5

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P20815 Link_out
Gene: CYP3A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate, inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

3. Cytochrome P450 3A7

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P24462 Link_out
Gene: CYP3A7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate, inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms

UniProt ID: P05181 Link_out
Gene: CYP2E1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol)

UniProt ID: P10632 Link_out
Gene: CYP2C8
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan

UniProt ID: P11712 Link_out
Gene: CYP2C9
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P04798 Link_out
Gene: CYP1A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development

UniProt ID: Q16678 Link_out
Gene: CYP1B1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate, inhibitor

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out
Gene: ABCB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 February 08, 2013 16:19