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
External IDs
LY-307640 / LY307640
Product Ingredients
IngredientUNIICASInChI Key
Rabeprazole sodium3L36P16U4R117976-90-6KRCQSTCYZUOBHN-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AcipHexTablet, delayed release20 mg/1OralEisai Inc.1999-08-19Not applicableUs62856 0243 30 nlmimage10 bb39dd9e
AcipHexTablet, delayed release20 mg/1OralCardinal Health1999-08-192016-04-30Us55154 245120180913 8702 v7pqav
AcipHexTablet, delayed release20 mg/1OralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-02-292014-12-31Us
AcipHexTablet, delayed release20 mg/1OralCarilion Materials Management1999-08-19Not applicableUs68151 383420180907 15195 j5bsd5
AcipHexTablet, delayed release20 mg/1Oralbryant ranch prepack1999-08-192006-09-30Us63629 273320180907 15195 13i2djl
AciphexTablet, delayed release20 mg/1OralPhysicians Total Care, Inc.2000-05-15Not applicableUs54868 418520180907 15195 16b0z58
AcipHex SprinkleCapsule, delayed release10 mg/1OralAvadel Pharmaceuticals (Usa), Inc.2014-10-012018-02-16Us
AcipHex SprinkleCapsule, delayed release5 mg/1OralAvadel Pharmaceuticals (Usa), Inc.2014-10-012018-02-16Us
AcipHex SprinkleCapsule, delayed release10 mg/1OralAytu Therapeutics, LLC2018-03-01Not applicableUs
AcipHex SprinkleCapsule, delayed release5 mg/1OralAytu Therapeutics, LLC2018-03-01Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Abbott-rabeprazoleTablet, delayed releaseOralBgp Pharma Ulc2014-07-212015-12-31Canada
Abbott-rabeprazoleTablet, delayed releaseOralBgp Pharma Ulc2014-10-172015-12-31Canada
Ag-rabeprazoleTablet, delayed releaseOralAngita Pharma Inc.Not applicableNot applicableCanada
Ag-rabeprazoleTablet, delayed releaseOralAngita Pharma Inc.Not applicableNot applicableCanada
Apo-rabeprazoleTablet, delayed releaseOralApotex Corporation2012-05-01Not applicableCanada
Apo-rabeprazoleTablet, delayed releaseOralApotex Corporation2012-05-01Not applicableCanada
Dom-rabeprazole ECTablet, delayed releaseOralDominion PharmacalNot applicableNot applicableCanada
Dom-rabeprazole ECTablet, delayed releaseOralDominion Pharmacal2012-09-26Not applicableCanada
Jamp RabeprazoleTablet, delayed releaseOralJamp Pharma CorporationNot applicableNot applicableCanada
Jamp RabeprazoleTablet, delayed releaseOralJamp Pharma CorporationNot applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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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
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Rabeprazole.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Rabeprazole.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Rabeprazole.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Rabeprazole.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be increased 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.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Rabeprazole.
9-DeazaguanineThe metabolism of 9-Deazaguanine can be increased when combined with Rabeprazole.
9-MethylguanineThe metabolism of 9-Methylguanine can be increased when combined with Rabeprazole.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
  • Take with or without food. Food delays drug absorption, but not to a clinically significant extent.

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 Drug
D08463
KEGG Compound
C07864
PubChem Compound
5029
PubChem Substance
46506366
ChemSpider
4853
BindingDB
50070209
RxNav
114979
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
A02BC54 — Rabeprazole, combinationsM01AA05 — ClofezoneA02BC04 — RabeprazoleM02AA03 — Clofezone
AHFS Codes
  • 56:28.36 — Proton-pump Inhibitors
FDA label
Download (135 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1CompletedNot AvailableGastroesophageal Reflux1
1CompletedNot AvailableHealthy Volunteers10
1CompletedBasic ScienceAutoimmune Diseases / Drug Drug Interaction (DDI) / Fibrotic Disease1
1CompletedBasic ScienceHealthy Volunteers9
1CompletedBasic ScienceHypergastrinemia1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1CompletedTreatmentDrug Interaction Potentiation / Pharmacokinetics1
1CompletedTreatmentGastro-esophageal Reflux Disease (GERD)3
1CompletedTreatmentGastroesophageal Reflux1
1CompletedTreatmentHealthy Volunteers13
1CompletedTreatmentMalignancies1
2CompletedNot AvailableGastroesophageal Reflux1
2CompletedDiagnosticPostnasal Drainage1
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, 3TerminatedTreatmentLiver Cirrhosis / Peptic Ulcer1
2, 3Unknown StatusTreatmentDuodenal Ulcer / Gastric Ulcer / Gastritis / Helicobacter Infections1
3Active Not RecruitingPreventionBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Early Gastric Cancer / Endoscopic Resection1
3CompletedPreventionAsthma / Gastro-esophageal Reflux Disease (GERD)1
3CompletedPreventionCardio-cerebrovascular Disease1
3CompletedPreventionGastric Lesion1
3CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
3CompletedTreatmentDyspepsia / Osteoarthritis (OA) / Rheumatoid Arthritis1
3CompletedTreatmentEsophageal Diseases1
3CompletedTreatmentGastro-esophageal Reflux Disease (GERD)7
3CompletedTreatmentGastroesophageal Reflux1
3CompletedTreatmentGastroesophageal Reflux / Heartburn2
3CompletedTreatmentHealthy Volunteers1
3CompletedTreatmentHeartburn2
3CompletedTreatmentNon-erosive Gastroesophageal Reflux Disease1
3CompletedTreatmentPeptic Ulcer Bleeding / Upper Gastrointestinal Hemorrhage1
3CompletedTreatmentSymptomatic Gastroesophageal Reflux Disease (sGERD)1
3Not Yet RecruitingTreatmentDuodenal Ulcer / Duodenal Ulcer,DU1
3RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
3Unknown StatusTreatmentGastro-esophageal Reflux Disease (GERD)1
3WithdrawnTreatmentGastro-esophageal Reflux Disease (GERD)1
4CompletedNot AvailableFrequent Heartburn1
4CompletedNot AvailableGastroesophageal Reflux1
4CompletedNot AvailableGastroesophageal Reflux / Pharyngeal Diseases1
4CompletedDiagnosticGastro-esophageal Reflux Disease (GERD)1
4CompletedOtherGastrointestinal Diseases2
4CompletedPreventionAdenocarcinoma, Tubular / Early Gastric Adenocarcinoma1
4CompletedPreventionNormal Subjects1
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)6
4CompletedTreatmentBacterial Infections / Helicobacter Infections1
4CompletedTreatmentGastric Ulcer1
4CompletedTreatmentGastro-Oesophageal Reflux1
4CompletedTreatmentGastro-esophageal Reflux Disease (GERD)3
4CompletedTreatmentGastro-esophageal Reflux Disease (GERD) / Insomnia1
4CompletedTreatmentGastroesophageal Reflux1
4CompletedTreatmentGastroesophageal Reflux / Heartburn1
4CompletedTreatmentHelicobacter Infections1
4CompletedTreatmentReflux Esophagitis (RE)2
4Not Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)3
4Not Yet RecruitingTreatmentGastro-esophageal Reflux Disease (GERD)1
4RecruitingPreventionAtrial Fibrillation (AF) / Venous Thromboembolism1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)4
4RecruitingTreatmentMalignant Neoplasm of Stomach1
4RecruitingTreatmentRefractory Reflux Esophagitis1
4TerminatedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4TerminatedTreatmentPeptic ulcer haemorrhage1
4Unknown StatusScreening30 Healthy People1
4Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
4Unknown StatusTreatmentGastritis, Gastric Ulcer, and Duodenal Ulcer1
4Unknown StatusTreatmentNonvariceal Upper Gastrointestinal Bleeding1
Not AvailableActive Not RecruitingNot AvailableGastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedNot AvailableCalcium Metabolism Disorders1
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 / Gastroesophageal Reflux1
Not AvailableCompletedTreatmentGastroesophageal Reflux / Laryngitis1
Not AvailableCompletedTreatmentPharmacodynamics1
Not AvailableCompletedTreatmentSigns and Symptoms1
Not AvailableEnrolling by InvitationTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Helicobacter Pylori Gastritis / Helicobacter-Associated Pyloric Ulcer1
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 AvailableGastroesophageal Reflux1
Not AvailableUnknown StatusDiagnosticGastro-esophageal Reflux Disease (GERD)1
Not AvailableUnknown StatusScreeningEsophagus, Barrett / Non-erosive Reflux Esophagitis Disease (NERD)1
Not AvailableUnknown StatusTreatmentChest Pain1
Not AvailableUnknown StatusTreatmentDuodenal Ulcer / Gastric Ulcer1
Not AvailableUnknown StatusTreatmentGastritis With H. Pylori Infection / Peptic Ulcer With H. Pylori Infection1

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, delayed releaseOral20 mg/1
Capsule, delayed releaseOral5 mg/1
Granule, delayed releaseOral10 mg/1
Granule, delayed releaseOral5 mg/1
Tablet, delayed releaseOral
Capsule, delayed releaseOral10 mg/1
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
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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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
Alkyl aryl ether / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Dialkyl ether / Ether / Heteroaromatic compound / Hydrocarbon derivative / Imidazole
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfoxide, pyridines, benzimidazoles (CHEBI:8768)

Targets

Kind
Protein
Organism
Humans
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
Humans
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. 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]
  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:15258107]
Kind
Protein
Organism
Humans
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. 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]
  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:15258107]
  3. 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]
  4. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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. 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]
Kind
Protein
Organism
Humans
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. 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
Humans
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
Humans
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
Humans
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
Humans
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 July 12, 2020 18:27

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