Rabeprazole
Identification
- Summary
Rabeprazole is a proton pump inhibitor used to help gastrointestinal ulcers heal, to treat symptoms of gastroesophageal reflux disease (GERD), to eradicate Helicobacter pylori, and to treat hypersecretory conditions such as Zollinger-Ellison Syndrome.
- Brand Names
- Aciphex, Pariet
- Generic Name
- Rabeprazole
- DrugBank Accession Number
- DB01129
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Rabeprazole (DB01129)
- Weight
- Average: 359.443
Monoisotopic: 359.130362243 - Chemical Formula
- C18H21N3O3S
- Synonyms
- Clofezone
- Rabeprazole
- External IDs
- LY-307640
- LY307640
Pharmacology
- Indication
For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism APotassium-transporting ATPase alpha chain 1 inhibitorHumans - Absorption
Absolute bioavailability is approximately 52%.
- Volume of distribution
Not Available
- Protein binding
96.3% (bound to human plasma proteins)
- Metabolism
Hepatic
Hover over products below to view reaction partners
- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Rabeprazole Metabolism Pathway Drug metabolism Rabeprazole Action Pathway Drug action - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2C19 CYP2C19*2A Not Available 681G>A Effect Inferred Increased gastric acid suppression. Details Cytochrome P450 2C19 CYP2C19*2B Not Available 681G>A Effect Inferred Increased gastric acid suppression. Details Cytochrome P450 2C19 CYP2C19*3 Not Available 636G>A Effect Inferred Increased gastric acid suppression. Details Cytochrome P450 2C19 CYP2C19*4 Not Available 1A>G Effect Inferred Increased gastric acid suppression. Details Cytochrome P450 2C19 CYP2C19*5 Not Available 1297C>T Effect Inferred Increased gastric acid suppression. Details Cytochrome P450 2C19 CYP2C19*6 Not Available 395G>A Effect Inferred Increased gastric acid suppression. Details Cytochrome P450 2C19 CYP2C19*7 Not Available 19294T>A Effect Inferred Increased gastric acid suppression. Details Cytochrome P450 2C19 CYP2C19*22 Not Available 557G>C / 991A>G Effect Inferred Increased gastric acid suppression. Details Cytochrome P450 2C19 CYP2C19*24 Not Available 99C>T / 991A>G … show all Effect Inferred Increased gastric acid suppression. Details Cytochrome P450 2C19 CYP2C19*35 Not Available 12662A>G Effect Inferred Increased 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Rabeprazole which could result in a higher serum level. Abatacept The metabolism of Rabeprazole can be increased when combined with Abatacept. Abemaciclib Rabeprazole may decrease the excretion rate of Abemaciclib which could result in a higher serum level. Abiraterone The metabolism of Rabeprazole can be decreased when combined with Abiraterone. Aceclofenac Aceclofenac may decrease the excretion rate of Rabeprazole which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Rabeprazole which could result in a higher serum level. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Rabeprazole. Acetaminophen Acetaminophen may decrease the excretion rate of Rabeprazole which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Rabeprazole which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Rabeprazole which could result in a higher serum level. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Take with or without food. Food delays drug absorption, but not to a clinically significant extent.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Rabeprazole sodium 3L36P16U4R 117976-90-6 KRCQSTCYZUOBHN-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Pariet
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aciphex Tablet, delayed release 20 mg/1 Oral Physicians Total Care, Inc. 2000-05-15 Not applicable US 
AcipHex Tablet, delayed release 20 mg/1 Oral Lake Erie Medical &Surgical Supply Dba Quality Care Products Llc 2012-02-29 2014-12-31 US AcipHex Tablet, delayed release 20 mg/1 Oral Carilion Materials Management 1999-08-19 Not applicable US 
AcipHex Tablet, delayed release 20 mg/1 Oral Eisai Inc. 1999-08-19 Not applicable US 
AcipHex Tablet, delayed release 20 mg/1 Oral bryant ranch prepack 1999-08-19 2006-09-30 US 
AcipHex Tablet, delayed release 20 mg/1 Oral Cardinal Health 1999-08-19 2016-04-30 US 
AcipHex Sprinkle Capsule, delayed release 10 mg/1 Oral Aytu Therapeutics, LLC 2018-03-01 Not applicable US AcipHex Sprinkle Granule, delayed release 10 mg/1 Oral Eisai Inc. 2013-03-26 2013-03-15 US AcipHex Sprinkle Capsule, delayed release 10 mg/1 Oral Avadel Pharmaceuticals (Usa), Inc. 2014-10-01 2018-02-16 US AcipHex Sprinkle Capsule, delayed release 5 mg/1 Oral Aytu Therapeutics, LLC 2018-03-01 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Abbott-rabeprazole Tablet, delayed release 10 mg Oral Bgp Pharma Ulc 2014-10-17 2015-12-31 Canada 
Abbott-rabeprazole Tablet, delayed release 20 mg Oral Bgp Pharma Ulc 2014-07-21 2015-12-31 Canada Aciphex Tablet, delayed release 20 mg/1 Oral Advanced Rx Pharmacy of Tennessee, LLC 2018-04-27 Not applicable US Aciphex Tablet, delayed release 20 mg/1 Oral Advanced Rx Pharmacy of Tennessee, LLC 2018-04-27 Not applicable US Ag-rabeprazole Tablet, delayed release 20 mg Oral Angita Pharma Inc. Not applicable Not applicable Canada Ag-rabeprazole Tablet, delayed release 10 mg Oral Angita Pharma Inc. Not applicable Not applicable Canada Apo-rabeprazole Tablet, delayed release 20 mg Oral Apotex Corporation 2012-05-01 Not applicable Canada Apo-rabeprazole Tablet, delayed release 10 mg Oral Apotex Corporation 2012-05-01 Not applicable Canada Dom-rabeprazole EC Tablet, delayed release 20 mg Oral Dominion Pharmacal 2012-09-26 Not applicable Canada Dom-rabeprazole EC Tablet, delayed release 10 mg Oral Dominion Pharmacal Not applicable Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image RABEDIC 10/75 MG MR KAPSÜL, 20 ADET Rabeprazole sodium (10 mg) + Diclofenac sodium (75 mg) Capsule Oral TAKEDA İLAÇ SAĞLIK SAN. TİC. LTD. ŞTİ. 2020-08-14 2017-12-06 Turkey 
RABEDIC 10/75 MG MR KAPSÜL, 30 ADET Rabeprazole sodium (10 mg) + Diclofenac sodium (75 mg) Capsule Oral TAKEDA İLAÇ SAĞLIK SAN. TİC. LTD. ŞTİ. 2020-08-14 2017-12-06 Turkey RABEDIC 20/75 MG MR KAPSÜL, 20 ADET Rabeprazole sodium (20 mg) + Diclofenac sodium (75 mg) Capsule Oral TAKEDA İLAÇ SAĞLIK SAN. TİC. LTD. ŞTİ. 2020-08-14 2017-12-06 Turkey RABEDIC 20/75 MG MR KAPSÜL, 30 ADET Rabeprazole sodium (20 mg) + Diclofenac sodium (75 mg) Capsule Oral TAKEDA İLAÇ SAĞLIK SAN. TİC. LTD. ŞTİ. 2020-08-14 2017-12-06 Turkey RABEDIC MR 20/100 MG KAPSÜL, 20 ADET Rabeprazole sodium (20 mg) + Diclofenac sodium (100 mg) Capsule Oral TAKEDA İLAÇ SAĞLIK SAN. TİC. LTD. ŞTİ. 2020-08-14 2017-12-06 Turkey RABEDIC MR 20/100 MG KAPSÜL, 30 ADET Rabeprazole sodium (20 mg) + Diclofenac sodium (100 mg) Capsule Oral TAKEDA İLAÇ SAĞLIK SAN. TİC. LTD. ŞTİ. 2020-08-14 2017-12-06 Turkey RABELIS PLUS 20/10 MG KAPSUL, 30 ADET Rabeprazole sodium (20 mg) + Domperidone maleate (10 mg) Capsule Oral VİTALİS İLAÇ SAN. TİC. A.Ş. 2020-08-14 Not applicable Turkey RABELIS PLUS 20/30 MG MR KAPSUL, 30 ADET Rabeprazole sodium (20 mg) + Domperidone maleate (30 mg) Capsule Oral VİTALİS İLAÇ SAN. TİC. A.Ş. 2020-08-14 Not applicable Turkey RASOFORCE 20/1680 MG TOZ İÇEREN SAŞE, 14 SAŞE Rabeprazole sodium (20 mg) + Sodium bicarbonate (1680 mg) Powder, for suspension Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey RASOFORCE 20/1680 MG TOZ İÇEREN SAŞE, 28 SAŞE Rabeprazole sodium (20 mg) + Sodium bicarbonate (1680 mg) Powder, for suspension Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey
Categories
- ATC Codes
- A02BD12 — Rabeprazole, amoxicillin and clarithromycin
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BC — Proton pump inhibitors
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- M01AA — Butylpyrazolidines
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL SYSTEM
- A02BC — Proton pump inhibitors
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- 2-Pyridinylmethylsulfinylbenzimidazoles
- Acetates
- Acid Reducers
- Acids, Acyclic
- Alimentary Tract and Metabolism
- Anti-Ulcer Agents
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antiinflammatory Preparations, Non-Steroids for Topical Use
- BCRP/ABCG2 Inhibitors
- Benzimidazoles
- Butylpyrazolidines
- Cytochrome P-450 CYP1A2 Inducers
- Cytochrome P-450 CYP1A2 Inducers (strength unknown)
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (moderate)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs for Acid Related Disorders
- Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Fatty Acids
- Fatty Acids, Volatile
- Gastric Acid Lowering Agents
- Gastrointestinal Agents
- Heterocyclic Compounds, Fused-Ring
- Hydroxy Acids
- Lipids
- Musculo-Skeletal System
- Proton Pump Inhibitors
- Proton-pump Inhibitors
- Pyrazoles
- Pyrazolones
- Pyridines
- Sulfoxides
- Sulfur Compounds
- Topical Products for Joint and Muscular Pain
- Chemical TaxonomyProvided by Classyfire
- 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)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 32828355LL
- CAS number
- 117976-89-3
- 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
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
- 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
- FDA label
- Download (135 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Diagnostic Gastro-esophageal Reflux Disease (GERD) 1 4 Completed Other Gastrointestinal Diseases 2 4 Completed Prevention Adenocarcinoma, Tubular / Early Gastric Adenocarcinoma 1 4 Completed Prevention Normal Subjects 1 4 Completed Treatment Bacterial Infections / Helicobacter Infections 1 4 Completed Treatment Gastric Ulcer 1 4 Completed Treatment Gastro-esophageal Reflux Disease (GERD) 3 4 Completed Treatment Gastro-esophageal Reflux Disease (GERD) / Insomnia 1 4 Completed Treatment Gastroesophageal Reflux 2 4 Completed Treatment Gastroesophageal Reflux / Heartburn 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
Form Route Strength Tablet, coated Oral 10 mg Tablet, delayed release Oral 20 mg/1 Capsule, delayed release Oral 5 mg/1 Granule, delayed release Oral 10 mg/1 Granule, delayed release Oral 5 mg/1 Tablet, extended release Oral Tablet, film coated Oral 20 mg Tablet, delayed release Oral 10 mg Tablet, delayed release Oral 20 mg Tablet, film coated Oral Tablet, film coated Oral 10 mg Tablet, coated Oral 20 mg Tablet, coated Oral 5 MG Capsule Oral Tablet, delayed release Oral Capsule, delayed release Oral 10 mg/1 Tablet Oral Tablet Oral 10 MG Tablet Oral 20 MG Capsule Oral Powder, for suspension Oral - Prices
Unit description Cost Unit Aciphex 20 mg Enteric Coated Tabs 7.48USD tab Aciphex ec 20 mg tablet 6.08USD tablet Aciphex 20 mg tablet ec 5.9USD tablet Pariet 20 mg Enteric-Coated Tablet 1.46USD tablet Apo-Rabeprazole 20 mg Enteric-Coated Tablet 0.82USD tablet Novo-Rabeprazole 20 mg Enteric-Coated Tablet 0.82USD tablet Pms-Rabeprazole Ec 20 mg Enteric-Coated Tablet 0.82USD tablet Ran-Rabeprazole 20 mg Enteric-Coated Tablet 0.82USD tablet Sandoz Rabeprazole 20 mg Enteric-Coated Tablet 0.82USD tablet Pariet 10 mg Enteric-Coated Tablet 0.73USD tablet Apo-Rabeprazole 10 mg Enteric-Coated Tablet 0.41USD tablet Novo-Rabeprazole 10 mg Enteric-Coated Tablet 0.41USD tablet Pms-Rabeprazole Ec 10 mg Enteric-Coated Tablet 0.41USD tablet Ran-Rabeprazole 10 mg Enteric-Coated Tablet 0.41USD tablet Sandoz Rabeprazole 10 mg Enteric-Coated Tablet 0.41USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5045552 No 1991-09-03 2013-05-08 US CA2104531 No 1999-01-05 2013-08-20 Canada CA1336958 No 1995-09-12 2012-09-12 Canada
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 0.6 Not Available - Predicted Properties
Property Value Source Water Solubility 0.336 mg/mL ALOGPS logP 2.04 ALOGPS logP 2.09 ChemAxon logS -3 ALOGPS pKa (Strongest Acidic) 9.35 ChemAxon pKa (Strongest Basic) 4.24 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 77.1 Å2 ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 98.07 m3·mol-1 ChemAxon Polarizability 39.64 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9967 Blood Brain Barrier + 0.6469 Caco-2 permeable + 0.6664 P-glycoprotein substrate Substrate 0.6179 P-glycoprotein inhibitor I Inhibitor 0.5835 P-glycoprotein inhibitor II Non-inhibitor 0.9387 Renal organic cation transporter Inhibitor 0.6194 CYP450 2C9 substrate Non-substrate 0.8265 CYP450 2D6 substrate Non-substrate 0.8623 CYP450 3A4 substrate Substrate 0.7174 CYP450 1A2 substrate Inhibitor 0.6677 CYP450 2C9 inhibitor Non-inhibitor 0.7734 CYP450 2D6 inhibitor Non-inhibitor 0.7875 CYP450 2C19 inhibitor Inhibitor 0.6661 CYP450 3A4 inhibitor Non-inhibitor 0.6647 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7243 Ames test Non AMES toxic 0.5726 Carcinogenicity Non-carcinogens 0.8751 Biodegradation Not ready biodegradable 0.939 Rat acute toxicity 2.4215 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.5726 hERG inhibition (predictor II) Non-inhibitor 0.8733
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- Langtry HD, Markham A: Rabeprazole: a review of its use in acid-related gastrointestinal disorders. Drugs. 1999 Oct;58(4):725-42. [Article]
- Carswell CI, Goa KL: Rabeprazole: an update of its use in acid-related disorders. Drugs. 2001;61(15):2327-56. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorInducer
- 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
- 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. [Article]
- Zvyaga T, Chang SY, Chen C, Yang Z, Vuppugalla R, Hurley J, Thorndike D, Wagner A, Chimalakonda A, Rodrigues AD: Evaluation of six proton pump inhibitors as inhibitors of various human cytochromes P450: focus on cytochrome P450 2C19. Drug Metab Dispos. 2012 Sep;40(9):1698-711. doi: 10.1124/dmd.112.045575. Epub 2012 May 30. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- Zvyaga T, Chang SY, Chen C, Yang Z, Vuppugalla R, Hurley J, Thorndike D, Wagner A, Chimalakonda A, Rodrigues AD: Evaluation of six proton pump inhibitors as inhibitors of various human cytochromes P450: focus on cytochrome P450 2C19. Drug Metab Dispos. 2012 Sep;40(9):1698-711. doi: 10.1124/dmd.112.045575. Epub 2012 May 30. [Article]
- 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
References
- Zvyaga T, Chang SY, Chen C, Yang Z, Vuppugalla R, Hurley J, Thorndike D, Wagner A, Chimalakonda A, Rodrigues AD: Evaluation of six proton pump inhibitors as inhibitors of various human cytochromes P450: focus on cytochrome P450 2C19. Drug Metab Dispos. 2012 Sep;40(9):1698-711. doi: 10.1124/dmd.112.045575. Epub 2012 May 30. [Article]
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
- 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. [Article]
Drug created on June 13, 2005 13:24 / Updated on October 24, 2021 16:00