REBAMIPIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H15ClN2O4
Molecular Weight	370.786
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C(CC1=CC(=O)NC2=C1C=CC=C2)NC(=O)C3=CC=C(Cl)C=C3

InChI

InChIKey=ALLWOAVDORUJLA-UHFFFAOYSA-N

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)

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9753220
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/rebamipide.html | http://www.mims.com/philippines/drug/info/rebamipide?mtype=generic | https://www.ncbi.nlm.nih.gov/pubmed/27098506

Rebamipide, an amino acid derivative of 2-(1H)-quinolinone, is used for mucosal protection, healing of gastroduodenal ulcers, and treatment of gastritis. It works by enhancing mucosal defense, scavenging free radicals, and temporarily activating genes encoding cyclooxygenase-2. Rebamipide is used in a number of Asian countries including Japan (marketed as Mucosta), South Korea, China, and India (where it is marketed under the trade name Rebagen). It is not approved by the Food and Drug Administration for use in the United States. Studies have shown that rebamipide can fight the damaging effects of NSAIDs on the GIT mucosa.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
AMP-activated protein kinase, AMPK 17 Target ID: CHEMBL2096907 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28011266	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Peptic ulcer 72 Sources: http://www.mims.com/philippines/drug/info/rebamipide?mtype=generic	Primary	Approved 8429	Mucosta Approved Use Unknown
Gastritis 45 Sources: http://www.mims.com/philippines/drug/info/rebamipide?mtype=generic	Primary	Approved 8429	Mucosta Approved Use Unknown
Gastropathy 2 Sources: https://clinicaltrials.gov/ct2/show/NCT00641004	Primary	Phase IV 63	Mucosta Approved Use Unknown

PubMed

Title	Date	PubMed
Double-blind placebo-controlled multicentre studies of rebamipide, a gastroprotective drug, in the treatment of functional dyspepsia with or without Helicobacter pylori infection.	2001 Oct	11564000
Long-term rebamipide therapy improves Helicobacter pylori-associated chronic gastritis.	2002 Apr	11991622
Oxidative stress induced cytokine production in isolated rat pancreatic acinar cells: effects of small-molecule antioxidants.	2002 Feb	11803245
[Effect of antiulcer agents on the urea breath test--Comparison between rebamipide and ecabet sodium].	2002 Jan	11831005
Local gastric and serum concentrations of rebamipide following oral ingestion in healthy volunteers.	2002 Jun	12064818
Modulatory effects of plasma and colonic milieu of patients with ulcerative colitis on neutrophil reactive oxygen species production in presence of a novel antioxidant, rebamipide.	2002 Jun	12064811
Bioequivalence of rebamipide granules and tablets in healthy adult male volunteers.	2003	17536891
Study of inhibition of CYP2A6 by some drugs derived from quinoline.	2003 Dec	14738594
Characteristics of attenuating effects of rebamipide, an anti-ulcer agent, on oxidative burst of human neutrophils.	2003 Feb	12686760
Effects of antioxidative agents on apoptosis induced by ischaemia-reperfusion in rat intestinal mucosa.	2003 Jul	12925152
The effect of rebamipide on the expression of proinflammatory mediators and apoptosis in human neutrophils by Helicobacter pylori water-soluble surface proteins.	2003 Jul	12925140
Effect of long-term administration of rebamipide on Helicobacter pylori infection in mice.	2003 Jul	12925138
[Agranulocytosis due to anti-tuberculosis drugs including isoniazid (INH) and rifampicin (RFP)--a report of four cases and review of the literature].	2003 Nov	14672045
Rebamipide activates genes encoding angiogenic growth factors and Cox2 and stimulates angiogenesis: a key to its ulcer healing action?	2004 Feb	15104358
Rebamipide inhibits gastric cancer growth by targeting survivin and Aurora-B.	2005 Aug 19	15993841
Radical scavengers: a remedy for presbyacusis. A pilot study.	2005 Dec	16303676
NADPH oxidase mediates interleukin-6 expression in cerulein-stimulated pancreatic acinar cells.	2005 Jul	15833277
[Enema therapy for ulcerative colitis patients].	2005 May	15881180
Rebamipide reduces indomethacin-induced gastric injury in mice via down-regulation of ICAM-1 expression.	2005 Oct	16184426
Effect of a gastro-protective agent, rebamipide, on symptom improvement in patients with functional dyspepsia: a double-blind placebo-controlled study in Japan.	2006 Dec	17074021
Optimization of suppository preparation containing sodium laurate and taurine that can safely improve rectal absorption of rebamipide.	2006 Feb	16462041
OPC-12759 increases proliferation of cultured rat conjunctival goblet cells.	2006 Jun	16783146
[Case of drug-induced lung injury due to Rebamipide].	2006 Oct	17087338
Rebamipide inhibits gastric cancer cell growth.	2007 Jan	17171453

Patents

Sample Use Guides

In Vivo Use Guide

100 mg tid, in the morning, evening and before bedtime.

Route of Administration: Oral

In Vitro Use Guide

Human gastric carcinoma AGS cells were treated with rebamipide at 0.1-5mkM for 2 h. Cells were lysed followed by western blot analysis. The blots were probed with an anti-p-AMPKalpha antibody specific for threonine 172-phosphorylated AMPKalpha.

Name

Type

Language

REBAMIPIDE

Official Name

English

REBAMIPIDE [MI]

Common Name

English

REBATOR

Brand Name

English

(±)-.ALPHA.-(P-CHLOROBENZAMIDO)-1,2-DIHYDRO-2-OXO-4-QUINOLINEPROPIONIC ACID

Common Name

English

NSC-758955

Code

English

MUCOSTA

Brand Name

English

PROAMIPIDE

Brand Name

English

4-QUINOLINEPROPANOIC ACID, .ALPHA.-((4-CHLOROBENZOYL)AMINO)-1,2-DIHYDRO-2-OXO-

Systematic Name

English

rebamipide [INN]

Common Name

English

REBAMIPIDE [JAN]

Common Name

English

OPC-12759

Code

English

Rebamipide [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

A02BX14