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rabeprazole   Click here for help

GtoPdb Ligand ID: 7290

Synonyms: AcipHex® | E-3810 | Pariet®
Approved drug
rabeprazole is an approved drug (FDA (1999))
Compound class: Synthetic organic
Comment: Rabeprazole is a proton pump inhibitor. This compound is a prodrug which is converted into the active sulphenamide form in the acid environment of the parietal cells.
Marketed formulations may contain rabeprazole sodium (PubChem CID 14720269).
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View more information in the IUPHAR Pharmacology Education Project: rabeprazole

rabeprazole is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 96.31
Molecular weight 359.13
XLogP 0.63
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COCCCOc1ccnc(c1C)CS(=O)c1nc2c([nH]1)cccc2
Isomeric SMILES COCCCOc1ccnc(c1C)CS(=O)c1nc2c([nH]1)cccc2
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)
InChI Key YREYEVIYCVEVJK-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Used to promote healing and symptomatic relief in patients with duodenal ulcers and erosive or ulcerative gastroesophageal reflux disease (GERD). This drug is also used to treat hypersecretion of gastric acid associated with other pathological conditions.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Rabeprazole irreversibly inhibits the gastric potassium-transporting ATPase. This proton pump is responsible for secreting H+ ions into the stomach, creating acidic pH. View further gene and protein details for the transporter subunits on the H+/K+-ATPases page.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com