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Identification
Name Omeprazole
Accession Number DB00338 (APRD00446)
Type small molecule
Groups approved
Description

A highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers and zollinger-ellison syndrome. The drug inhibits the H()-K()-ATPase (H()-K()-exchanging ATPase) in the proton pump of gastric parietal cells. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
OMEP
Omeprazol [INN-Spanish]
Omeprazole magnesium
Omeprazolum [INN-Latin]
OMZ
Salts Not Available
Brand names
Name Company
Antra
Audazol
Aulcer
Belmazol
Ceprandal
Danlox
Demeprazol
Desec
Dizprazol
Dudencer
Elgam
Emeproton
Epirazole
Erbolin
Exter
Gasec
Gastrimut
Gastroloc
Gibancer
Indurgan
Inhibitron
Inhipump
Lensor
Logastric
Lomac
Losec
Mepral
Miol
Miracid
Mopral
Morecon
Nilsec
Nopramin
Ocid
Olexin
Omapren
Omebeta 20
Omed
Omegast
Omepral
Omeprazon
Omeprol
Omesek
Omezol
Omezolan
Omid
Omisec
Omizac
Ompanyt
Ortanol
Osiren
Ozoken
Paprazol
Parizac
Pepticum
Pepticus
Peptilcer
Prazentol
Prazidec
Prazolit
Prilosec
Procelac
Proclor
Prysma
Ramezol
Regulacid
Result
Sanamidol
Secrepina
Tedec Ulceral
Ulceral
Ulcesep
Ulcometion
Ulcozol
Ulcsep
Ulsen
Ultop
Ulzol
Victrix
Zefxon
Zegerid
Zepral
Zimor
Zoltum
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Brand mixtures Not Available
Categories
  • Anti-Ulcer Agents
  • Enzyme Inhibitors
  • Proton-pump Inhibitors
CAS number 73590-58-6
Weight Average: 345.416
Monoisotopic: 345.114712179
Chemical Formula C17H19N3O3S
InChI Key InChIKey=SUBDBMMJDZJVOS-UHFFFAOYSA-N
InChI
InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)
Plain Text
IUPAC Name
6-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methane]sulfinyl}-1H-1,3-benzodiazole
SMILES
COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(C)C(OC)=C1C
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Benzimidazoles
  • Ethers
  • Anisoles
Substructures
  • Phenols and Derivatives
  • Benzimidazoles
  • Pyridines and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Imidazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Imines
  • Cyanamides
  • Phenyl Esters
  • Sulfoxides
Pharmacology
Indication For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
Pharmacodynamics Omeprazole is a compound that inhibits gastric acid secretion and is indicated in the treatment of gastroesophageal reflux disease (GERD), the healing of erosive esophagitis, and H. pylori eradication to reduce the risk of duodenal ulcer recurrence. Omeprazole belongs to a new class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or H2 histamine antagonistic properties, but that suppress gastric acid secretion by specific inhibition of the H+/K+ ATPase at the secretory surface of the gastric parietal cell. As a result, it inhibits acid secretion into the gastric lumen. This effect is dose-related and leads to inhibition of both basal and stimulated acid secretion irrespective of the stimulus.
Mechanism of action Omeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the H+/K+-ATPase in the gastric parietal cell. By acting specifically on the proton pump, omeprazole blocks the final step in acid production, thus reducing gastric acidity.
Absorption Absorption is rapid, absolute bioavailability (compared to intravenous administration) is about 30-40% at doses of 20-40 mg.
Volume of distribution Not Available
Protein binding 95%
Metabolism Hepatic.
Route of elimination Urinary excretion is a primary route of excretion of omeprazole metabolites.
Half life 0.5-1 hour
Clearance
  • total body cl=500-600 mL/min [healthy]
  • 250 mL/min [Geriatric]
  • 70 mL/min [Hepatic Impairment]
  • 10 – 62 mL/min/1.73 m2 [Renal Impairment]
Toxicity Symptoms of overdose include confusion, drowsiness, blurred vision, tachycardia, nausea, diaphoresis, flushing, headache, and dry mouth.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00226 Omeprazole Pathway SMP00226
Pharmacoeconomics
Manufacturers
  • Apotex inc
  • Dr reddys laboratories ltd
  • Impax laboratories inc
  • Kremers urban development co
  • Lek pharmaceuticals d d
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Watson laboratories inc florida
  • Astrazeneca lp
  • Dexcel pharma technologies ltd
  • Santarus, Inc.
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Capsule, delayed release Oral
Tablet, delayed release Oral
Prices
Unit description Cost Unit
PriLOSEC 30 20 mg Delayed Release Capsule Bottle 459.99 USD bottle
Zegerid 30 20-1680 mg Packets Packet 224.27 USD packet
Zegerid 30 40-1680 mg Packets Packet 224.27 USD packet
PriLOSEC 30 10 mg Delayed Release Capsule Bottle 174.37 USD bottle
Omeprazole 28 20 mg Enteric Coated Tabs Box 25.99 USD box
PriLOSEC OTC 14 20 mg Enteric Coated Tabs Box 19.99 USD box
PriLOSEC 40 mg Delayed Release Capsule 9.59 USD capsule
Prilosec dr 40 mg capsule 9.22 USD capsule
Omeprazole 40 mg Delayed Release Capsule 7.69 USD capsule
Zegerid 40-1100 mg capsule 7.48 USD capsule
Zegerid 20 mg capsule 7.19 USD capsule
Zegerid 40 mg capsule 6.46 USD capsule
Prilosec dr 20 mg capsule 6.24 USD capsule
Prilosec 20 mg capsule dr 6.15 USD capsule
Prilosec dr 10 mg capsule 5.59 USD capsule
Omeprazole powder 5.05 USD g
Omeprazole 20 mg Delayed Release Capsule 4.32 USD capsule
Omeprazole 10 mg Delayed Release Capsule 3.13 USD capsule
Losec (Sustained-Release Tablet) 20 mg Capsule/Sustained Release Tablet 2.48 USD tablet
Losec (Sustained-Release Tablet) 10 mg Capsule/Sustained Release Tablet 1.97 USD tablet
Losec (Sustained-Release Capsule) 20 mg Capsule/Sustained Release Tablet 1.24 USD tablet
Apo-Omeprazole 20 mg Capsule/Sustained Release Tablet 1.15 USD tablet
Mylan-Omeprazole 20 mg Capsule/Sustained Release Tablet 1.15 USD tablet
Pms-Omeprazole (Delayed Release Tablet) 20 mg Capsule/Sustained Release Tablet 1.15 USD tablet
Pms-Omeprazole (Sustained-Release Capsule) 20 mg Capsule/Sustained Release Tablet 1.15 USD tablet
Ratio-Omeprazole (Sustained-Release Tablet) 20 mg Capsule/Sustained Release Tablet 1.15 USD tablet
Sandoz Omeprazole (Sustained-Release Capsule) 20 mg Capsule/Sustained Release Tablet 1.15 USD tablet
Mylan-Omeprazole 10 mg Capsule/Sustained Release Tablet 0.86 USD tablet
Sandoz Omeprazole (Sustained-Release Capsule) 10 mg Capsule/Sustained Release Tablet 0.86 USD tablet
Zegerid otc 20-1100 mg capsule 0.78 USD capsule
Prilosec otc 20 mg tablet 0.76 USD tablet
Omeprazole dr 20 mg tablet 0.66 USD tablet
CVS Pharmacy omeprazole dr 20 mg tablet 0.53 USD tablet
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
United States 6403616 1999-11-15 2019-11-15
United States 5690960 1994-11-25 2014-11-25
Canada 2180535 2004-03-23 2014-01-05
Canada 1338377 1996-06-11 2013-06-11
Properties
State solid
Experimental Properties
Property Value Source
melting point 156 °C PhysProp
water solubility 82.3 mg/L Not Available
logP 2.23 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 3.59e-01 g/l ALOGPS
logP 1.66 ALOGPS
logP 2.43 ChemAxon
logS -3 ALOGPS
pKa (strongest acidic) 9.29 ChemAxon
pKa (strongest basic) 4.77 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 77.1 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 93.66 ChemAxon
polarizability 37.45 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Yang YX, Lewis JD, Epstein S, Metz DC: Long-term proton pump inhibitor therapy and risk of hip fracture. JAMA. 2006 Dec 27;296(24):2947-53. Pubmed
External Links
Resource Link
KEGG Drug D00455 Link_out
KEGG Compound C07324 Link_out
PubChem Compound 4594 Link_out
PubChem Substance 46509065 Link_out
ChemSpider 4433 Link_out
BindingDB 50241343 Link_out
ChEBI 7772 Link_out
ChEMBL 7772 Link_out
Therapeutic Targets Database DAP000180 Link_out
PharmGKB PA450704 Link_out
IUPHAR 4279 Link_out
Guide to Pharmacology 4279 Link_out
Drug Product Database 2260867 Link_out
RxList http://www.rxlist.com/cgi/generic/omepra.htm Link_out
Drugs.com http://www.drugs.com/omeprazole.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pri1350.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Omeprazole Link_out
ATC Codes
  • A02BC01
  • A02BC05
AHFS Codes
  • 56:28.36
PDB Entries Not Available
FDA label show (218 KB)
MSDS show (73.8 KB)
Interactions
Drug Interactions
Drug Interaction
Alprazolam Omeprazole may increase the effect of the benzodiazepine, alprazolam.
Atazanavir This gastric pH modifier decreases the levels/effects of atazanavir
Bendamustine Affects hepatic CYP1A2 metabolism, thus increasing bendamustine levels. Concentration of active metabolites may be decreased due to decreased conversion.
Cefditoren Proton pump inhibitors such as omeprazole may decrease the serum concentration of cefditoren. If possible, avoid use of cefditoren with proton pump inhibitors (PPIs). Consider alternative methods to minimize/control acid reflux (eg, diet modification) or alternative antimicrobial therapy if use of PPIs can not be avoided.
Chlordiazepoxide Omeprazole may increase the effect of the benzodiazepine, chlordiazepoxide.
Cilostazol Omeprazole increases the effect of cilostazol
Clonazepam Omeprazole may increase the effect of the benzodiazepine, clonazepam.
Clopidogrel Omeprazole may decrease serum concentrations of the active metabolite(s) of clopidogrel. Clopidogrel prescribing information recommends avoiding concurrent use with omeprazole, due to the possibility that combined use may result in decreased clopidogrel effectiveness.
Clorazepate Omeprazole may increase the effect of the benzodiazepine, clorazepate.
Cyclosporine Omeprazole increases the effect and toxicity of cyclosporine
Dasatinib Omeprazole may decrease the serum level of dasatinib.
Diazepam Omeprazole may increase the effect of the benzodiazepine, diazepam.
Disopyramide The beta-blocker increases toxicity of disopyramide
Enoxacin Omeprazole may decrease the absorption of enoxacin.
Estazolam Omeprazole may increase the effect of the benzodiazepine, estazolam.
Ethotoin Omeprazole increases the effect of hydantoin
Flurazepam Omeprazole may increase the effect of the benzodiazepine, flurazepam.
Fosphenytoin Omeprazole increases the effect of hydantoin
Halazepam Omeprazole may increase the effect of the benzodiazepine, halazepam.
Indinavir Omeprazole decreases the absorption of indinavir
Itraconazole The proton pump inhibitor, omeprazole, may decrease the absorption of itraconazole.
Ketazolam Omeprazole may increase the effect of the benzodiazepine, ketazolam.
Ketoconazole The proton pump inhibitor, omeprazole, may decrease the absorption of ketoconazole.
Mephenytoin Omeprazole increases the effect of hydantoin
Methotrexate Omeprazole increases the levels of methotrexate
Midazolam Omeprazole may increase the effect of the benzodiazepine, midazolam.
Phenytoin Omeprazole increases the effect of hydantoin
Prazepam Omeprazole may increase the effect of the benzodiazepine, prazepam.
Quazepam Omeprazole may increase the effect of the benzodiazepine, quazepam.
St. John's Wort St. John's Wort decreases the levels/effects of omeprazole
Tacrolimus Omeprazole may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Omeprazole therapy is initiated, discontinued or altered.
Tipranavir Tipranavir, co-administered with Ritonavir, may decrease the plasma concentration of Omeprazole. Consider alternate therapy or increase the dose of Omeprazole based on the therapeutic response.
Triazolam Omeprazole may increase the effect of the benzodiazepine, triazolam.
Trimipramine The strong CYP2C19 inhibitor, Omeprazole, may decrease the metabolism and clearance of Trimipramine, a CYP2C19 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimipramine if Omeprazole is initiated, discontinued or dose changed.
Vismodegib Vismodegib serum concentrations may be decreased by proton pump inhibitors such as omeprazole.
Voriconazole Voriconazole increases the effect and toxicity of omeprazole
Food Interactions
  • Avoid alcohol.
  • Take 30-60 minutes before meals.
Targets

1. Potassium-transporting ATPase alpha chain 1

Pharmacological action: yes
Actions: inhibitor

Catalyzes the hydrolysis of ATP coupled with the exchange of H(+) and K(+) ions across the plasma membrane. Responsible for acid production in the stomach

Organism class: human
UniProt ID: P20648 Link_out
Gene: ATP4A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Tajima A, Koizumi K, Suzuki K, Higashi N, Takahashi M, Shimada T, Terano A, Hiraishi H, Kuwayama H: Proton pump inhibitors and recurrent bleeding in peptic ulcer disease. J Gastroenterol Hepatol. 2008 Dec;23 Suppl 2:S237-41. Pubmed
  2. Shi S, Klotz U: Proton pump inhibitors: an update of their clinical use and pharmacokinetics. Eur J Clin Pharmacol. 2008 Oct;64(10):935-51. Epub 2008 Aug 5. Pubmed
  3. Kirchheiner J, Glatt S, Fuhr U, Klotz U, Meineke I, Seufferlein T, Brockmoller J: Relative potency of proton-pump inhibitors-comparison of effects on intragastric pH. Eur J Clin Pharmacol. 2009 Jan;65(1):19-31. Epub 2008 Oct 17. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Enzymes

1. Cytochrome P450 2C19

Actions: substrate, inhibitor

Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Foti RS, Wahlstrom JL: CYP2C19 inhibition: the impact of substrate probe selection on in vitro inhibition profiles. Drug Metab Dispos. 2008 Mar;36(3):523-8. Epub 2007 Nov 29. Pubmed
  2. Li XQ, Andersson TB, Ahlstrom M, Weidolf L: Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos. 2004 Aug;32(8):821-7. Pubmed
  3. Li XQ, Weidolf L, Simonsson R, Andersson TB: Enantiomer/enantiomer interactions between the S- and R- isomers of omeprazole in human cytochrome P450 enzymes: major role of CYP2C19 and CYP3A4. J Pharmacol Exp Ther. 2005 Nov;315(2):777-87. Epub 2005 Aug 10. Pubmed
  4. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  5. 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
  6. 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. Yamazaki H, Inoue K, Shaw PM, Checovich WJ, Guengerich FP, Shimada T: Different contributions of cytochrome P450 2C19 and 3A4 in the oxidation of omeprazole by human liver microsomes: effects of contents of these two forms in individual human samples. J Pharmacol Exp Ther. 1997 Nov;283(2):434-42. Pubmed

2. Cytochrome P450 3A4

Actions: substrate, inhibitor, inducer

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. Li XQ, Weidolf L, Simonsson R, Andersson TB: Enantiomer/enantiomer interactions between the S- and R- isomers of omeprazole in human cytochrome P450 enzymes: major role of CYP2C19 and CYP3A4. J Pharmacol Exp Ther. 2005 Nov;315(2):777-87. Epub 2005 Aug 10. Pubmed
  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. Botsch S, Gautier JC, Beaune P, Eichelbaum M, Kroemer HK: Identification and characterization of the cytochrome P450 enzymes involved in N-dealkylation of propafenone: molecular base for interaction potential and variable disposition of active metabolites. Mol Pharmacol. 1993 Jan;43(1):120-6. 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. Turpeinen M, Uusitalo J, Jalonen J, Pelkonen O: Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32. Pubmed

3. Cytochrome P450 1A2

Actions: substrate, inhibitor, inducer

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

4. Cytochrome P450 2C9

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. 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

5. Cytochrome P450 2C18

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: P33260 Link_out
Gene: CYP2C18 Link_out
Protein 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

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. 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 2D6

Actions: inhibitor

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

8. Cholesterol side-chain cleavage enzyme, mitochondrial

Actions: inhibitor

Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone

UniProt ID: P05108 Link_out
Gene: CYP11A1 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 1A1

Actions: inducer

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

10. Cytochrome P450 1B1

Actions: inducer

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
Transporters

1. Canalicular multispecific organic anion transporter 2

Actions: inducer

May act as an inducible transporter in the biliary and intestinal excretion of organic anions

UniProt ID: O15438 Link_out
Gene: ABCC3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hitzl M, Klein K, Zanger UM, Fritz P, Nussler AK, Neuhaus P, Fromm MF: Influence of omeprazole on multidrug resistance protein 3 expression in human liver. J Pharmacol Exp Ther. 2003 Feb;304(2):524-30. Pubmed

2. Multidrug resistance protein 1

Actions: 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. Pauli-Magnus C, Rekersbrink S, Klotz U, Fromm MF: Interaction of omeprazole, lansoprazole and pantoprazole with P-glycoprotein. Naunyn Schmiedebergs Arch Pharmacol. 2001 Dec;364(6):551-7. Pubmed

3. ATP-binding cassette sub-family G member 2

Actions: inhibitor

Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123

UniProt ID: Q9UNQ0 Link_out
Gene: ABCG2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Breedveld P, Zelcer N, Pluim D, Sonmezer O, Tibben MM, Beijnen JH, Schinkel AH, van Tellingen O, Borst P, Schellens JH: Mechanism of the pharmacokinetic interaction between methotrexate and benzimidazoles: potential role for breast cancer resistance protein in clinical drug-drug interactions. Cancer Res. 2004 Aug 15;64(16):5804-11. Pubmed
  2. Suzuki K, Doki K, Homma M, Tamaki H, Hori S, Ohtani H, Sawada Y, Kohda Y: Co-administration of proton pump inhibitors delays elimination of plasma methotrexate in high-dose methotrexate therapy. Br J Clin Pharmacol. 2009 Jan;67(1):44-9. Epub 2008 Nov 17. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19