rebamipide   Click here for help

GtoPdb Ligand ID: 871

Synonyms: OPC-12759 | pramipide
Approved drug
rebamipide is an approved drug
Compound class: Synthetic organic
Comment: Rebamipide is an amino acid derivative of 2-(1H)-quinolinone with gastroprotective action [1].
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

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

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 99.26
Molecular weight 370.07
XLogP 3.55
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES Clc1ccc(cc1)C(=O)NC(C(=O)O)Cc1cc(=O)[nH]c2c1cccc2
Isomeric SMILES Clc1ccc(cc1)C(=O)NC(C(=O)O)Cc1cc(=O)[nH]c2c1cccc2
InChI InChI=1S/C19H15ClN2O4/c20-13-7-5-11(6-8-13)18(24)22-16(19(25)26)9-12-10-17(23)21-15-4-2-1-3-14(12)15/h1-8,10,16H,9H2,(H,21,23)(H,22,24)(H,25,26)
InChI Key ALLWOAVDORUJLA-UHFFFAOYSA-N
References
1. Arakawa T, Kobayashi K, Yoshikawa T, Tarnawski A. (1998)
Rebamipide: overview of its mechanisms of action and efficacy in mucosal protection and ulcer healing.
Dig Dis Sci, 43 (9 Suppl): 5S-13S. [PMID:9753220]
2. Arakawa T, Watanabe T, Fukuda T, Yamasaki K, Kobayashi K. (1995)
Rebamipide, novel prostaglandin-inducer accelerates healing and reduces relapse of acetic acid-induced rat gastric ulcer. Comparison with cimetidine.
Dig Dis Sci, 40 (11): 2469-72. [PMID:7587834]
3. Ishihara K, Komuro Y, Nishiyama N, Yamasaki K, Hotta K. (1992)
Effect of rebamipide on mucus secretion by endogenous prostaglandin-independent mechanism in rat gastric mucosa.
Arzneimittelforschung, 42 (12): 1462-6. [PMID:1337697]
4. Kleine A, Kluge S, Peskar BM. (1993)
Stimulation of prostaglandin biosynthesis mediates gastroprotective effect of rebamipide in rats.
Dig Dis Sci, 38 (8): 1441-9. [PMID:8393757]
5. Moon SJ, An JM, Kim J, Lee SI, Ahn W, Kim KH, Seo JT. (2004)
Pharmacological characterization of rebamipide: its cholecystokinin CCK1 receptor binding profile and effects on Ca2+ mobilization and amylase release in rat pancreatic acinar cells.
Eur J Pharmacol, 505 (1-3): 61-6. [PMID:15556137]
6. Tarnawski AS, Chai J, Pai R, Chiou SK. (2004)
Rebamipide activates genes encoding angiogenic growth factors and Cox2 and stimulates angiogenesis: a key to its ulcer healing action?.
Dig Dis Sci, 49 (2): 202-9. [PMID:15104358]
7. Yoshikawa T, Naito Y, Tanigawa T, Kondo M. (1993)
Free radical scavenging activity of the novel anti-ulcer agent rebamipide studied by electron spin resonance.
Arzneimittelforschung, 43 (3): 363-6. [PMID:8387788]