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
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)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/9753220Curator'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
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 |
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Target ID: CHEMBL2096907 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28011266 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Mucosta Approved UseUnknown |
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Primary | Mucosta Approved UseUnknown |
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Primary | Mucosta Approved UseUnknown |
PubMed
Title | Date | PubMed |
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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 |
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Long-term rebamipide therapy improves Helicobacter pylori-associated chronic gastritis. | 2002 Apr |
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Oxidative stress induced cytokine production in isolated rat pancreatic acinar cells: effects of small-molecule antioxidants. | 2002 Feb |
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[Effect of antiulcer agents on the urea breath test--Comparison between rebamipide and ecabet sodium]. | 2002 Jan |
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Local gastric and serum concentrations of rebamipide following oral ingestion in healthy volunteers. | 2002 Jun |
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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 |
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Bioequivalence of rebamipide granules and tablets in healthy adult male volunteers. | 2003 |
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Study of inhibition of CYP2A6 by some drugs derived from quinoline. | 2003 Dec |
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Characteristics of attenuating effects of rebamipide, an anti-ulcer agent, on oxidative burst of human neutrophils. | 2003 Feb |
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Effects of antioxidative agents on apoptosis induced by ischaemia-reperfusion in rat intestinal mucosa. | 2003 Jul |
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The effect of rebamipide on the expression of proinflammatory mediators and apoptosis in human neutrophils by Helicobacter pylori water-soluble surface proteins. | 2003 Jul |
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Effect of long-term administration of rebamipide on Helicobacter pylori infection in mice. | 2003 Jul |
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[Agranulocytosis due to anti-tuberculosis drugs including isoniazid (INH) and rifampicin (RFP)--a report of four cases and review of the literature]. | 2003 Nov |
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Rebamipide activates genes encoding angiogenic growth factors and Cox2 and stimulates angiogenesis: a key to its ulcer healing action? | 2004 Feb |
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Rebamipide inhibits gastric cancer growth by targeting survivin and Aurora-B. | 2005 Aug 19 |
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Radical scavengers: a remedy for presbyacusis. A pilot study. | 2005 Dec |
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NADPH oxidase mediates interleukin-6 expression in cerulein-stimulated pancreatic acinar cells. | 2005 Jul |
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[Enema therapy for ulcerative colitis patients]. | 2005 May |
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Rebamipide reduces indomethacin-induced gastric injury in mice via down-regulation of ICAM-1 expression. | 2005 Oct |
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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 |
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Optimization of suppository preparation containing sodium laurate and taurine that can safely improve rectal absorption of rebamipide. | 2006 Feb |
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OPC-12759 increases proliferation of cultured rat conjunctival goblet cells. | 2006 Jun |
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[Case of drug-induced lung injury due to Rebamipide]. | 2006 Oct |
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Rebamipide inhibits gastric cancer cell growth. | 2007 Jan |
Patents
Sample Use Guides
100 mg tid, in the morning, evening and before bedtime.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28011266
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.
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A02BX14
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C29701
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C29852
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Rebamipide
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ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)