Identification

Name
Rabeprazole
Accession Number
DB01129  (APRD01212)
Type
Small Molecule
Groups
Approved, Investigational
Description

Rabeprazole is an antiulcer drug in the class of proton pump inhibitors. It is a prodrug - in the acid environment of the parietal cells it turns into active sulphenamide form. Rabeprazole inhibits the H+, K+ATPase of the coating gastric cells and dose-dependent oppresses basal and stimulated gastric acid secretion.

Structure
Thumb
Synonyms
  • Clofezone
  • Rabeprazole
Product Ingredients
IngredientUNIICASInChI Key
Rabeprazole Sodium3L36P16U4R117976-90-6KRCQSTCYZUOBHN-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AcipHexTablet, delayed release20 mg/1OralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-02-292014-12-31Us
AcipHexTablet, coated20 mg/1Oralbryant ranch prepack1999-08-192018-09-14Us63629 273320180907 15195 13i2djl
AciphexTablet, delayed release20 mg/1OralPhysicians Total Care, Inc.2000-05-15Not applicableUs54868 418520180907 15195 16b0z58
AcipHexTablet, delayed release20 mg/1OralCardinal Health1999-08-192016-04-30Us55154 245120180913 8702 v7pqav
AcipHexTablet, delayed release20 mg/1OralCarilion Materials Management1999-08-19Not applicableUs68151 383420180907 15195 j5bsd5
AcipHexTablet, delayed release20 mg/1OralEisai Limited1999-08-19Not applicableUs62856 0243 30 nlmimage10 bb39dd9e
AcipHex SprinkleCapsule, delayed release10 mg/1OralAvadel Pharmaceuticals (Usa), Inc.2014-10-012018-08-24Us
AcipHex SprinkleGranule, delayed release10 mg/1OralEisai Inc.2013-03-262013-03-15Us
AcipHex SprinkleCapsule, delayed release10 mg/1OralZylera Pharmaceuticals, LLC2018-03-01Not applicableUs
AcipHex SprinkleCapsule, delayed release5 mg/1OralAvadel Pharmaceuticals (Usa), Inc.2014-10-012018-08-24Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Abbott-rabeprazoleTablet, delayed release20 mgOralBgp Pharma Ulc2014-07-212015-12-31Canada
Abbott-rabeprazoleTablet, delayed release10 mgOralBgp Pharma Ulc2014-10-172015-12-31Canada
Apo-rabeprazoleTablet, delayed release10 mgOralApotex Corporation2012-05-01Not applicableCanada
Apo-rabeprazoleTablet, delayed release20 mgOralApotex Corporation2012-05-01Not applicableCanada
Dom-rabeprazole ECTablet, delayed release20 mgOralDominion Pharmacal2012-09-26Not applicableCanada
Dom-rabeprazole ECTablet, delayed release10 mgOralDominion PharmacalNot applicableNot applicableCanada
Mylan-rabeprazoleTablet, delayed release20 mgOralMylan Pharmaceuticals2013-07-10Not applicableCanada
Mylan-rabeprazoleTablet, delayed release10 mgOralMylan Pharmaceuticals2013-07-10Not applicableCanada
Ntp-rabeprazole ECTablet, delayed release20 mgOralNt Pharma Canada LtdNot applicableNot applicableCanada
Ntp-rabeprazole ECTablet, delayed release10 mgOralNt Pharma Canada LtdNot applicableNot applicableCanada
International/Other Brands
Pariet
Categories
UNII
32828355LL
CAS number
117976-89-3
Weight
Average: 359.443
Monoisotopic: 359.130362243
Chemical Formula
C18H21N3O3S
InChI Key
YREYEVIYCVEVJK-UHFFFAOYSA-N
InChI
InChI=1S/C18H21N3O3S/c1-13-16(19-9-8-17(13)24-11-5-10-23-2)12-25(22)18-20-14-6-3-4-7-15(14)21-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,20,21)
IUPAC Name
2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
SMILES
COCCCOC1=C(C)C(CS(=O)C2=NC3=CC=CC=C3N2)=NC=C1

Pharmacology

Indication

For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.

Associated Conditions
Pharmacodynamics

Rabeprazole prevents the production of acid in the stomach. It reduces symptoms and prevents injury to the esophagus or stomach in patients with gastroesophageal reflux disease (GERD) or ulcers. Rabeprazole is also useful in conditions that produce too much stomach acid such as Zollinger-Ellison syndrome. Rabeprazole may also be used with antibiotics to get rid of bacteria that are associated with some ulcers. Rabeprazole is a selective and irreversible proton pump inhibitor, suppresses gastric acid secretion by specific inhibition of the H+, K+ -ATPase, which is found at the secretory surface of parietal cells. In doing so, it inhibits the final transport of hydrogen ions (via exchange with potassium ions) into the gastric lumen.

Mechanism of action

Rabeprazole belongs to a class of antisecretory compounds (substituted benzimidazole proton-pump inhibitors) that do not exhibit anticholinergic or histamine H2-receptor antagonist properties, but suppress gastric acid secretion by inhibiting the gastric H+/K+ATPase (hydrogen-potassium adenosine triphosphatase) at the secretory surface of the gastric parietal cell. Because this enzyme is regarded as the acid (proton) pump within the parietal cell, rabeprazole has been characterized as a gastric proton-pump inhibitor. Rabeprazole blocks the final step of gastric acid secretion. In gastric parietal cells, rabeprazole is protonated, accumulates, and is transformed to an active sulfenamide. When studied in vitro, rabeprazole is chemically activated at pH 1.2 with a half-life of 78 seconds.

TargetActionsOrganism
APotassium-transporting ATPase alpha chain 1
inhibitor
Human
Absorption

Absolute bioavailability is approximately 52%.

Volume of distribution
Not Available
Protein binding

96.3% (bound to human plasma proteins)

Metabolism

Hepatic

Route of elimination

Following a single 20 mg oral dose of 14C-labeled rabeprazole, approximately 90% of the drug was eliminated in the urine, primarily as thioether carboxylic acid; its glucuronide, and mercapturic acid metabolites.

Half life

1-2 hours (in plasma)

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Rabeprazole Metabolism PathwayDrug metabolism
Rabeprazole Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredIncreased gastric acid suppression.Details
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredIncreased gastric acid suppression.Details
Cytochrome P450 2C19CYP2C19*3Not Available636G>AEffect InferredIncreased gastric acid suppression.Details
Cytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredIncreased gastric acid suppression.Details
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredIncreased gastric acid suppression.Details
Cytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredIncreased gastric acid suppression.Details
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredIncreased gastric acid suppression.Details
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredIncreased gastric acid suppression.Details
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredIncreased gastric acid suppression.Details
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredIncreased gastric acid suppression.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Rabeprazole.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Rabeprazole.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Rabeprazole.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Rabeprazole.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Rabeprazole.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Rabeprazole.
6-Deoxyerythronolide BThe metabolism of Rabeprazole can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Rabeprazole.
8-azaguanineThe metabolism of 8-azaguanine can be increased when combined with Rabeprazole.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be increased when combined with Rabeprazole.
Food Interactions
  • Take without regard to meals.
  • Take without regard to meals. Food may slow absorption rate but extent of absorption is not affected.

References

Synthesis Reference

Sundaram Venkatraman, "Crystalline form Z of rabeprazole sodium and process for preparation thereof." U.S. Patent US20040180935, issued September 16, 2004.

US20040180935
General References
Not Available
External Links
Human Metabolome Database
HMDB0005026
KEGG Compound
C07864
PubChem Compound
5029
PubChem Substance
46506366
ChemSpider
4853
ChEBI
8768
ChEMBL
CHEMBL1219
Therapeutic Targets Database
DAP000727
PharmGKB
PA451216
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Rabeprazole
ATC Codes
A02BC04 — RabeprazoleM01AA05 — ClofezoneM02AA03 — ClofezoneA02BC54 — Rabeprazole, combinations
AHFS Codes
  • 56:28.36 — Proton-pump Inhibitors
FDA label
Download (135 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers4
1CompletedNot AvailableReflux, Gastroesophageal1
1CompletedBasic ScienceHealthy Volunteers7
1CompletedBasic ScienceHypergastrinemia1
1CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1CompletedTreatmentGastro-esophageal Reflux Disease (GERD)3
1CompletedTreatmentHealthy Volunteers11
1CompletedTreatmentReflux, Gastroesophageal1
1RecruitingBasic ScienceAutoimmune Diseases / Drug Drug Interaction (DDI) / Fibrotic Disease1
1RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2CompletedNot AvailableReflux, Gastroesophageal1
2CompletedTreatmentFunctional Dyspepsia2
2CompletedTreatmentGastro-esophageal Reflux Disease (GERD)3
2CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentReflux Esophagitis (RE)1
2, 3CompletedPreventionGastric Ulcers Duodenal Ulcers Caused by Low-dose Aspirin1
2, 3CompletedTreatmentDuodenal Ulcer1
2, 3CompletedTreatmentGastro-esophageal Reflux Disease (GERD)1
2, 3CompletedTreatmentLaryngopharyngeal Reflux1
2, 3CompletedTreatmentRefractory Reflux Esophagitis1
2, 3Unknown StatusTreatmentDuodenal Ulcer / Gastric Ulcer (GU) / Gastritis / Helicobacter Infections1
3CompletedPreventionAsthma Bronchial / Gastro-esophageal Reflux Disease (GERD)1
3CompletedPreventionCardio-cerebrovascular Disease1
3CompletedTreatmentGastro-esophageal Reflux Disease (GERD)6
3CompletedTreatmentHealthy Volunteers1
3CompletedTreatmentHeartburn2
3CompletedTreatmentHeartburn / Reflux, Gastroesophageal2
3CompletedTreatmentIndigestion / Osteoarthritis (OA) / Rheumatoid Arthritis1
3CompletedTreatmentNon-erosive Gastroesophageal Reflux Disease1
3CompletedTreatmentPeptic Ulcer Bleeding / Upper Gastrointestinal Hemorrhage1
3CompletedTreatmentReflux, Gastroesophageal1
3CompletedTreatmentSymptomatic Gastroesophageal Reflux Disease (sGERD)1
3Unknown StatusTreatmentGastro-esophageal Reflux Disease (GERD)1
3WithdrawnTreatmentGastro-esophageal Reflux Disease (GERD)1
4CompletedNot AvailableFrequent Heartburn1
4CompletedNot AvailablePharyngeal Diseases / Reflux, Gastroesophageal1
4CompletedNot AvailableReflux, Gastroesophageal1
4CompletedDiagnosticGastro-esophageal Reflux Disease (GERD)1
4CompletedPreventionAdenocarcinoma, Tubular / Early Gastric Adenocarcinoma1
4CompletedPreventionNormal Subjects1
4CompletedTreatmentBacterial Infections / Helicobacter Infections1
4CompletedTreatmentGastric Ulcer (GU)1
4CompletedTreatmentGastro-Oesophageal Reflux1
4CompletedTreatmentGastro-esophageal Reflux Disease (GERD)2
4CompletedTreatmentGastro-esophageal Reflux Disease (GERD) / Sleeplessness1
4CompletedTreatmentHeartburn / Reflux, Gastroesophageal1
4CompletedTreatmentHelicobacter Infections1
4CompletedTreatmentReflux Esophagitis (RE)2
4CompletedTreatmentReflux, Gastroesophageal1
4Not Yet RecruitingTreatmentGastro-esophageal Reflux Disease (GERD)1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)4
4RecruitingTreatmentMalignant Neoplasm of Stomach1
4RecruitingTreatmentRefractory Reflux Esophagitis1
4TerminatedTreatmentPeptic ulcer haemorrhage1
4Unknown StatusScreening30 Healthy People1
4Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Unknown StatusTreatmentGastritis, Gastric Ulcer, and Duodenal Ulcer1
4Unknown StatusTreatmentNonvariceal Upper Gastrointestinal Bleeding1
Not AvailableActive Not RecruitingNot AvailableGastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedNot AvailableCommunity Acquired Pneumonia (CAP) / Gastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedNot AvailableGastric Low-grade MALT Lymphoma With Helicobacter Pylori Positive1
Not AvailableCompletedNot AvailableHelicobacter Infections1
Not AvailableCompletedNot AvailableRefractory Reflux Esophagitis1
Not AvailableCompletedDiagnosticGastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedTreatmentBronchial Asthma / Reflux, Gastroesophageal1
Not AvailableCompletedTreatmentPharmacodynamics1
Not AvailableCompletedTreatmentSigns and Symptoms1
Not AvailableNot Yet RecruitingNot AvailableGastro-esophageal Reflux Disease (GERD)1
Not AvailableRecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
Not AvailableRecruitingTreatmentPeptic Ulcer Disease1
Not AvailableTerminatedNot AvailableReflux, Gastroesophageal1
Not AvailableUnknown StatusDiagnosticGastro-esophageal Reflux Disease (GERD)1
Not AvailableUnknown StatusScreeningEsophagus, Barrett / Non-erosive Reflux Disease (NERD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • Cardinal Health
  • Diversified Healthcare Services Inc.
  • DRX Pharmaceuticals
  • Eisai Inc.
  • Janssen-Ortho Inc.
  • Lake Erie Medical and Surgical Supply
  • Nucare Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
Dosage forms
FormRouteStrength
Tablet, coatedOral20 mg/1
Tablet, delayed releaseOral20 mg/1
Capsule, delayed releaseOral10 mg/1
Capsule, delayed releaseOral5 mg/1
Granule, delayed releaseOral10 mg/1
Granule, delayed releaseOral5 mg/1
Tablet, delayed releaseOral10 mg
Tablet, delayed releaseOral20 mg
Prices
Unit descriptionCostUnit
Aciphex 20 mg Enteric Coated Tabs7.48USD tab
Aciphex ec 20 mg tablet6.08USD tablet
Aciphex 20 mg tablet ec5.9USD tablet
Pariet 20 mg Enteric-Coated Tablet1.46USD tablet
Apo-Rabeprazole 20 mg Enteric-Coated Tablet0.82USD tablet
Novo-Rabeprazole 20 mg Enteric-Coated Tablet0.82USD tablet
Pms-Rabeprazole Ec 20 mg Enteric-Coated Tablet0.82USD tablet
Ran-Rabeprazole 20 mg Enteric-Coated Tablet0.82USD tablet
Sandoz Rabeprazole 20 mg Enteric-Coated Tablet0.82USD tablet
Pariet 10 mg Enteric-Coated Tablet0.73USD tablet
Apo-Rabeprazole 10 mg Enteric-Coated Tablet0.41USD tablet
Novo-Rabeprazole 10 mg Enteric-Coated Tablet0.41USD tablet
Pms-Rabeprazole Ec 10 mg Enteric-Coated Tablet0.41USD tablet
Ran-Rabeprazole 10 mg Enteric-Coated Tablet0.41USD tablet
Sandoz Rabeprazole 10 mg Enteric-Coated Tablet0.41USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5045552No1991-09-032013-05-08Us
CA2104531No1999-01-052013-08-20Canada
CA1336958No1995-09-122012-09-12Canada

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.336 mg/mLALOGPS
logP2.04ALOGPS
logP2.09ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.35ChemAxon
pKa (Strongest Basic)4.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.1 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity98.07 m3·mol-1ChemAxon
Polarizability39.64 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9967
Blood Brain Barrier+0.6469
Caco-2 permeable+0.6664
P-glycoprotein substrateSubstrate0.6179
P-glycoprotein inhibitor IInhibitor0.5835
P-glycoprotein inhibitor IINon-inhibitor0.9387
Renal organic cation transporterInhibitor0.6194
CYP450 2C9 substrateNon-substrate0.8265
CYP450 2D6 substrateNon-substrate0.8623
CYP450 3A4 substrateSubstrate0.7174
CYP450 1A2 substrateInhibitor0.6677
CYP450 2C9 inhibitorNon-inhibitor0.7734
CYP450 2D6 inhibitorNon-inhibitor0.7875
CYP450 2C19 inhibitorInhibitor0.6661
CYP450 3A4 inhibitorNon-inhibitor0.6647
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7243
Ames testNon AMES toxic0.5726
CarcinogenicityNon-carcinogens0.8751
BiodegradationNot ready biodegradable0.939
Rat acute toxicity2.4215 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5726
hERG inhibition (predictor II)Non-inhibitor0.8733
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
Sulfinylbenzimidazoles
Direct Parent
Sulfinylbenzimidazoles
Alternative Parents
Methylpyridines / Alkyl aryl ethers / Benzenoids / Imidazoles / Heteroaromatic compounds / Sulfoxides / Sulfinyl compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
Sulfinylbenzimidazole / Alkyl aryl ether / Methylpyridine / Pyridine / Benzenoid / Azole / Imidazole / Heteroaromatic compound / Sulfoxide / Sulfinyl compound
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfoxide, pyridines, benzimidazoles (CHEBI:8768)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sodium:potassium-exchanging atpase activity
Specific Function
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.
Gene Name
ATP4A
Uniprot ID
P20648
Uniprot Name
Potassium-transporting ATPase alpha chain 1
Molecular Weight
114117.74 Da
References
  1. Langtry HD, Markham A: Rabeprazole: a review of its use in acid-related gastrointestinal disorders. Drugs. 1999 Oct;58(4):725-42. [PubMed:10551440]
  2. Carswell CI, Goa KL: Rabeprazole: an update of its use in acid-related disorders. Drugs. 2001;61(15):2327-56. [PubMed:11772142]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Shimizu M, Uno T, Yasui-Furukori N, Sugawara K, Tateishi T: Effects of clarithromycin and verapamil on rabeprazole pharmacokinetics between CYP2C19 genotypes. Eur J Clin Pharmacol. 2006 Aug;62(8):597-603. Epub 2006 Jun 17. [PubMed:16783561]
  3. 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:15258107]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Shimizu M, Uno T, Yasui-Furukori N, Sugawara K, Tateishi T: Effects of clarithromycin and verapamil on rabeprazole pharmacokinetics between CYP2C19 genotypes. Eur J Clin Pharmacol. 2006 Aug;62(8):597-603. Epub 2006 Jun 17. [PubMed:16783561]
  3. 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:15258107]
  4. Yamazaki H, Suzuki M, Tane K, Shimada N, Nakajima M, Yokoi T: In vitro inhibitory effects of troglitazone and its metabolites on drug oxidation activities of human cytochrome P450 enzymes: comparison with pioglitazone and rosiglitazone. Xenobiotica. 2000 Jan;30(1):61-70. [PubMed:10659951]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
Curator comments
Studies are limited to in vitro evidence.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Krusekopf S, Roots I, Hildebrandt AG, Kleeberg U: Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics. Xenobiotica. 2003 Feb;33(2):107-18. [PubMed:12623754]
Details
5. Cytochrome P450 2C9
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. 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:15258107]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. 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:15258107]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. 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. doi: 10.1111/j.1365-2125.2008.03303.x. Epub 2008 Nov 17. [PubMed:19076159]

Drug created on June 13, 2005 07:24 / Updated on November 18, 2018 04:49