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Identification
NameOmeprazole
Accession NumberDB00338  (APRD00446)
TypeSmall Molecule
GroupsApproved, Investigational
Description

A highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers and Zollinger-Ellison syndrome. Omeprazole belongs to a class of antisecretory compounds, the substituted benzimidazoles, that suppress gastric acid secretion by specific inhibition of the H+/K+ ATPase enzyme system at the secretory surface of the gastric parietal cell.

Structure
Thumb
Synonyms
SynonymLanguageCode
OMEPNot AvailableNot Available
OMPNot AvailableNot Available
OMZNot AvailableNot Available
PrilosecNot AvailableNot Available
Salts
Name/CAS Structure Properties
Omeprazole magnesium
Thumb
  • InChI Key: KWORUUGOSLYAGD-UHFFFAOYNA-N
  • Monoisotopic Mass: 712.198816192
  • Average Mass: 713.121
DBSALT000131
Omeprazole sodium
Thumb Not applicable DBSALT000857
Brand names
NameCompany
AntraNot Available
AudazolNot Available
BelmazolNot Available
CeprandalNot Available
DanloxNot Available
DesecNot Available
ElgamNot Available
EmeprotonNot Available
GasecNot Available
GastrimutNot Available
GastrolocNot Available
IndurganNot Available
InhibitronNot Available
LogastricNot Available
LosecNot Available
MepralNot Available
MopralNot Available
OlexinNot Available
OmaprenNot Available
OmepralNot Available
OmeprazonNot Available
OmeprolNot Available
OmezolNot Available
OmisecNot Available
OmizacNot Available
OrtanolNot Available
ParizacNot Available
PrazidecNot Available
PrazolitNot Available
PrilosecNot Available
ProcelacNot Available
RamezolNot Available
RegulacidNot Available
SanamidolNot Available
UlceralNot Available
UlcesepNot Available
UltopNot Available
ZegeridNot Available
ZepralNot Available
Brand mixturesNot Available
Categories
CAS number73590-58-6
WeightAverage: 345.416
Monoisotopic: 345.114712179
Chemical FormulaC17H19N3O3S
InChI KeySUBDBMMJDZJVOS-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)
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzimidazoles
SubclassSulfinylbenzimidazoles
Direct parentSulfinylbenzimidazoles
Alternative parentsAnisoles; Alkyl Aryl Ethers; Pyridines and Derivatives; Imidazoles; Sulfoxides; Polyamines
Substituentsphenol ether; anisole; alkyl aryl ether; pyridine; benzene; imidazole; azole; sulfoxide; ether; polyamine; organonitrogen compound
Classification descriptionThis compound belongs to the sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
Pharmacology
IndicationOmeprazole is indicated for the treatment of duodenal ulcers, benign gastric ulcers, gastroesophageal reflux disease (GERD), heartburn and other symptoms associated with GERD, erosive esophagitis, and long-term treatment of pathological hypersecretory conditions like Zollinger-Ellison syndrome, multiple endocrine adenomas, and systemic mastocytosis.
PharmacodynamicsAfter oral administration, the onset of the anti-secretory effect of omeprazole occurs within one hour and maximum effect occurring within two hours. At 24 hours, inhibition of secretion is approximately 50% of maximum and duration of inhibition lasts up to 72 hours. Although omeprazole has a very short plasma half-life, the anti-secretory effect lasts for a long time due to prolonged binding to parietal H+/K+ ATPase enzyme. When the drug has been discontinued, secretory activity will return to baseline over 3-5 days. The inhibitory effect of omeprazole on acid secretion increases with repeated once-daily dosing, reaching a plateau after four days. In studies involving more than 200 patients, serum gastrin levels increased during the first 1 to 2 weeks of once-daily administration of therapeutic doses of omeprazole in parallel with inhibition of acid secretion. Systemic effects of omeprazole in the CNS, cardiovascular and respiratory systems have not been found to date.
Mechanism of actionOmeprazole 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.
AbsorptionThe delayed-release capsule are enteric-coated (as omeprazole is acid-labile) so the absorption of omprazole begins once the granules leave the stomach. Absorption is rapid. Peak plasma levels occur within 0.5 - 3.5 hours. The absolute bioavailability (compared with intravenous administration) of the delayed-release capsule is 30-40% at doses of 20 - 40 mg, due to presystemic metabolism. This value increases slightly when given repeatedly. Based on a relative bioavailability study, the AUC and Cmax of PRILOSEC (omeprazole magnesium) for Delayed-Release Oral Suspension were 87% and 88% of those for PRILOSEC Delayed-Release Capsules, respectively. Interestingly, when the 40 mg delayed release capsule is given with or without applesauce, it is bioequivalent. However, when the 20 mg delayed release capsule is given with the same conditions, it is not bioequivalent. When the same capsule is given to the elderly, bioavailability increases. Omeprazole was 76% bioavailable.
Volume of distributionNot Available
Protein binding95% bound to human plasma protein.
Metabolism

Hepatic. Omeprazole is extensively metabolized by the cytochrome P450 (CYP) enzyme system. The two primary CYP isozymes involved are CYP2C19 and CYP3A4. Metabolism is stereoselective in which the S-isomer is converted to 5'O-desmethylomeprazole via CYP2C19. CYP3A4 converts the S-isomer to 3-hydroxyomeprazole. The R-isomer is converted to 5-hydroxyomeprazole by CYP2C19. CYP3A4 converts the R-isomer to any four different metabolites: 5-hydroxyomeprazole (5-OH OME), omeprazole sulfone (OME sulfone), 5'-O-desmethylomeprazole (5'-desmethyl OME), and 3-hydroxyomeprazole (3-OH OME).

SubstrateEnzymesProduct
Omeprazole
5-HydroxyomeprazoleDetails
Omeprazole
5'-O-Desmethyl omeprazoleDetails
Omeprazole
Omeprazole sulfoneDetails
Omeprazole
3-HydroxyomeprazoleDetails
Route of eliminationUrinary excretion is a primary route of excretion of omeprazole metabolites. Little, if any unchanged drug was excreted in the urine. The majority of the dose (about 77%) was eliminated in urine as at least six metabolites. Two were identified as hydroxyomeprazole and the corresponding carboxylic acid. The remainder of the dose was recovered in the feces.
Half life0.5-1 hour (healthy subjects, delayed-release capsule); 3 hours (hepatic impairment)
Clearance
  • 500 – 600 mL/min [Total body clearance, healthy subjects, delayed-release capsule]
  • 250 mL/min [Plasma clearance, Geriatric]
  • 70 mL/min [Plasma clearance, Hepatic Impairment]
ToxicitySymptoms of overdose include confusion, drowsiness, blurred vision, tachycardia, nausea, diaphoresis, flushing, headache, and dry mouth.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Cytochrome P450 2C19
Gene symbol: CYP2C19
UniProt: P33261
rs4244285 CYP2C19*2A Allele, homozygotePoor metabolizer, lower dose requirement, improved drug efficacy9867757
Cytochrome P450 2C19
Gene symbol: CYP2C19
UniProt: P33261
rs4986893 CYP2C19*3A Allele, homozygotePoor metabolizer, lower dose requirement, improved drug efficacy9867757
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9968
Blood Brain Barrier - 0.6326
Caco-2 permeable + 0.8867
P-glycoprotein substrate Non-substrate 0.5573
P-glycoprotein inhibitor I Inhibitor 0.6622
P-glycoprotein inhibitor II Non-inhibitor 0.968
Renal organic cation transporter Non-inhibitor 0.542
CYP450 2C9 substrate Non-substrate 0.7838
CYP450 2D6 substrate Substrate 0.6175
CYP450 3A4 substrate Substrate 0.6901
CYP450 1A2 substrate Inhibitor 0.7505
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Inhibitor 0.8994
CYP450 3A4 substrate Inhibitor 0.796
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7895
Ames test Non AMES toxic 0.5692
Carcinogenicity Non-carcinogens 0.8318
Biodegradation Not ready biodegradable 0.9778
Rat acute toxicity 2.2254 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.719
hERG inhibition (predictor II) Non-inhibitor 0.8977
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
FormRouteStrength
Capsule, delayed releaseOral10 mg, 20 mg, 40 mg
SuspensionOral2 mg/mL
Tablet, delayed releaseOral20 mg
Prices
Unit descriptionCostUnit
PriLOSEC 30 20 mg Delayed Release Capsule Bottle459.99USDbottle
Zegerid 30 20-1680 mg Packets Packet224.27USDpacket
Zegerid 30 40-1680 mg Packets Packet224.27USDpacket
PriLOSEC 30 10 mg Delayed Release Capsule Bottle174.37USDbottle
Omeprazole 28 20 mg Enteric Coated Tabs Box25.99USDbox
PriLOSEC OTC 14 20 mg Enteric Coated Tabs Box19.99USDbox
PriLOSEC 40 mg Delayed Release Capsule9.59USDcapsule
Prilosec dr 40 mg capsule9.22USDcapsule
Omeprazole 40 mg Delayed Release Capsule7.69USDcapsule
Zegerid 40-1100 mg capsule7.48USDcapsule
Zegerid 20 mg capsule7.19USDcapsule
Zegerid 40 mg capsule6.46USDcapsule
Prilosec dr 20 mg capsule6.24USDcapsule
Prilosec 20 mg capsule dr6.15USDcapsule
Prilosec dr 10 mg capsule5.59USDcapsule
Omeprazole powder5.05USDg
Omeprazole 20 mg Delayed Release Capsule4.32USDcapsule
Omeprazole 10 mg Delayed Release Capsule3.13USDcapsule
Losec (Sustained-Release Tablet) 20 mg Capsule/Sustained Release Tablet2.48USDtablet
Losec (Sustained-Release Tablet) 10 mg Capsule/Sustained Release Tablet1.97USDtablet
Losec (Sustained-Release Capsule) 20 mg Capsule/Sustained Release Tablet1.24USDtablet
Apo-Omeprazole 20 mg Capsule/Sustained Release Tablet1.15USDtablet
Mylan-Omeprazole 20 mg Capsule/Sustained Release Tablet1.15USDtablet
Pms-Omeprazole (Delayed Release Tablet) 20 mg Capsule/Sustained Release Tablet1.15USDtablet
Pms-Omeprazole (Sustained-Release Capsule) 20 mg Capsule/Sustained Release Tablet1.15USDtablet
Ratio-Omeprazole (Sustained-Release Tablet) 20 mg Capsule/Sustained Release Tablet1.15USDtablet
Sandoz Omeprazole (Sustained-Release Capsule) 20 mg Capsule/Sustained Release Tablet1.15USDtablet
Mylan-Omeprazole 10 mg Capsule/Sustained Release Tablet0.86USDtablet
Sandoz Omeprazole (Sustained-Release Capsule) 10 mg Capsule/Sustained Release Tablet0.86USDtablet
Zegerid otc 20-1100 mg capsule0.78USDcapsule
Prilosec otc 20 mg tablet0.76USDtablet
Omeprazole dr 20 mg tablet0.66USDtablet
CVS Pharmacy omeprazole dr 20 mg tablet0.53USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States64036161999-11-152019-11-15
United States56909601994-11-252014-11-25
Canada21805352004-03-232014-01-05
Canada13383771996-06-112013-06-11
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point155 °CFDA label
water solubilityVery slightly soluble FDA label
logP2.23SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.359ALOGPS
logP1.66ALOGPS
logP2.43ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)4.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.1 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.66 m3·mol-1ChemAxon
Polarizability37.45 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra1D NMR2D NMR
References
Synthesis Reference

Arne E. Brandstrom, Bo R. Lamm, “Processes for the preparation of omeprazole and intermediates therefore.” U.S. Patent US4620008, issued October, 1982.

US4620008
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
  2. FDA label
External Links
ResourceLink
KEGG DrugD00455
KEGG CompoundC07324
PubChem Compound4594
PubChem Substance46509065
ChemSpider4433
BindingDB50241343
ChEBI7772
ChEMBLCHEMBL1503
Therapeutic Targets DatabaseDAP000180
PharmGKBPA450704
IUPHAR4279
Guide to Pharmacology4279
Drug Product Database2260867
RxListhttp://www.rxlist.com/cgi/generic/omepra.htm
Drugs.comhttp://www.drugs.com/omeprazole.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pri1350.shtml
WikipediaOmeprazole
ATC CodesA02BC01A02BC05
AHFS Codes
  • 56:28.36
PDB EntriesNot Available
FDA labelshow(218 KB)
MSDSshow(73.8 KB)
Interactions
Drug Interactions
Drug
AlprazolamOmeprazole may increase the effect of the benzodiazepine, alprazolam.
AtazanavirThis gastric pH modifier decreases the levels/effects of atazanavir
AvanafilNineteen healthy male volunteers received a single 40 omeprazole delayed-release capsule once daily for 8 days (Days 1-8), and a single 200 mg avanafil on Day 8. Twelve hour pharmacokinetics of omeprazole on Days 7 and 8 were compared. Co-administration with avanafil resulted in an approximate 5.9% increase in AUC0-inf and 8.6% increase in Cmax of omeprazole.
BendamustineAffects hepatic CYP1A2 metabolism, thus increasing bendamustine levels. Concentration of active metabolites may be decreased due to decreased conversion.
CefditorenProton 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.
ChlordiazepoxideOmeprazole may increase the effect of the benzodiazepine, chlordiazepoxide.
CilostazolOmeprazole increases the effect of cilostazol
ClonazepamOmeprazole may increase the effect of the benzodiazepine, clonazepam.
ClopidogrelOmeprazole 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.
ClorazepateOmeprazole may increase the effect of the benzodiazepine, clorazepate.
CyclosporineOmeprazole increases the effect and toxicity of cyclosporine
DasatinibOmeprazole may decrease the serum level of dasatinib.
DiazepamOmeprazole may increase the effect of the benzodiazepine, diazepam.
DisopyramideThe beta-blocker increases toxicity of disopyramide
EnoxacinOmeprazole may decrease the absorption of enoxacin.
EstazolamOmeprazole may increase the effect of the benzodiazepine, estazolam.
EthotoinOmeprazole increases the effect of hydantoin
FlurazepamOmeprazole may increase the effect of the benzodiazepine, flurazepam.
FosphenytoinOmeprazole increases the effect of hydantoin
HalazepamOmeprazole may increase the effect of the benzodiazepine, halazepam.
IndinavirOmeprazole decreases the absorption of indinavir
ItraconazoleThe proton pump inhibitor, omeprazole, may decrease the absorption of itraconazole.
KetazolamOmeprazole may increase the effect of the benzodiazepine, ketazolam.
KetoconazoleThe proton pump inhibitor, omeprazole, may decrease the absorption of ketoconazole.
MephenytoinOmeprazole increases the effect of hydantoin
MethotrexateOmeprazole increases the levels of methotrexate
MidazolamOmeprazole may increase the effect of the benzodiazepine, midazolam.
OspemifeneModerate CYP2C19 inhibitors may increase levels of ospemifene. Monitor concomitant therapy closely.
PhenytoinOmeprazole increases the effect of hydantoin
PrazepamOmeprazole may increase the effect of the benzodiazepine, prazepam.
QuazepamOmeprazole may increase the effect of the benzodiazepine, quazepam.
RilpivirineProton-pump inhibitors increase gastric pH which causes a decrease in the exposure of rilpivirine thus reducing efficacy.
RoflumilastAffects CYP1A2 metabolism; decreases level or effect of roflumilast.
St. John's WortSt. John's Wort decreases the levels/effects of omeprazole
TacrolimusOmeprazole 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.
TipranavirTipranavir, 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.
TocilizumabOmeprazole is a CYP2C19 and CYP3A4 substrate. Exposure of omeprazole decreases following administration of tocilizumab..
TriazolamOmeprazole may increase the effect of the benzodiazepine, triazolam.
TrimipramineThe 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.
VismodegibVismodegib serum concentrations may be decreased by proton pump inhibitors such as omeprazole.
VoriconazoleVoriconazole 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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Potassium-transporting ATPase alpha chain 1 P20648 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

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

5. Cytochrome P450 2C18

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C18 P33260 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

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. 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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

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

8. Cholesterol side-chain cleavage enzyme, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 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 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

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

10. Cytochrome P450 1B1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

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

Transporters

1. Canalicular multispecific organic anion transporter 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Canalicular multispecific organic anion transporter 2 O15438 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
ATP-binding cassette sub-family G member 2 Q9UNQ0 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:09