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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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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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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1999)
IUPAC Name Click here for help
2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
International Nonproprietary Names Click here for help
INN number INN
7112 rabeprazole
Synonyms Click here for help
AcipHex® | E-3810 | Pariet®
Database Links Click here for help
CAS Registry No. 17976-89-3
ChEMBL Ligand CHEMBL1219
DrugBank Ligand DB01129
DrugCentral Ligand 2350
GtoPdb PubChem SID 178103864
PubChem CID 5029
Search Google for chemical match using the InChIKey YREYEVIYCVEVJK-UHFFFAOYSA-N
Search Google for chemicals with the same backbone YREYEVIYCVEVJK
Search PubMed clinical trials rabeprazole
Search PubMed titles rabeprazole
Search PubMed titles/abstracts rabeprazole
UniChem Compound Search for chemical match using the InChIKey YREYEVIYCVEVJK-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey YREYEVIYCVEVJK-UHFFFAOYSA-N
Wikipedia Rabeprazole

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MedChemExpress
Rabeprazole (links to external site)
Cat. No. HY-B0656