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)
DescriptionCurator'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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of rebamipide on mucus secretion by endogenous prostaglandin-independent mechanism in rat gastric mucosa. | 1992 Dec |
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| The inhibitory mechanism of rebamipide on the mediator release in the guinea pig lung mast cells activated with specific antigen-antibody reactions. | 2001 |
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| Rebamipide suppresses formyl-methionyl-leucyl-phenylalanine (fMLP)-induced superoxide production by inhibiting fMLP-receptor binding in human neutrophils. | 2001 Apr |
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| Rebamipide inhibits ceramide-induced interleukin-8 production in Kato III human gastric cancer cells. | 2001 Aug |
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| Alterations of epithelial permeability by Helicobacter and IL-1beta in vitro: protective effect of rebamipide. | 2001 Jul |
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| Rebamipide prevents periarterial blood-induced vasospasm in the rat femoral artery model. | 2001 May |
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| Expression of cyclooxygenase-2 in human neutrophils activated by Helicobacter pylori water-soluble proteins: possible involvement of NF-kappaB and MAP kinase signaling pathway. | 2001 Oct |
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| The antioxidant effect of rebamipide on oxygen free radical production by H. pylori-activated human neutrophils: in comparison with N-acetylcysteine, ascorbic acid and glutathione. | 2001 Oct |
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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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| Effects of anti-ulcer agents on ethanol-induced gastric mucosal lesions in D-galactosamine-induced hepatitis rats. | 2002 |
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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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| [A case of rebamipide-induced pneumonitis]. | 2002 Jan |
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| Involvement of cytochrome P450 in the metabolism of rebamipide by the human liver. | 2002 Jul |
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| Efficacy of rebamipide as adjunctive therapy in the treatment of recurrent oral aphthous ulcers in patients with Behçet's disease: a randomised, double-blind, placebo-controlled study. | 2003 |
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| Combinatorial use of sodium laurate with taurine or L-glutamine enhances colonic absorption of rebamipide, poorly absorbable antiulcer drug, without any serious histopathological mucosal damages. | 2003 Apr |
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| Radical scavengers for Ménière's disease after failure of conventional therapy: a pilot study. | 2003 Aug |
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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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| Effect of rebamipide on acetic acid-induced gastric ulcer in rats: involvement of hepatocyte growth factor. | 2003 Feb |
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| Influence of lansoprazole, famotidine, roxatidine and rebamipide administration on the urea breath test for the diagnosis of Helicobacter pylori infection. | 2003 Feb |
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| Chemoprevention of Helicobacter pylori-associated gastric carcinogenesis in a mouse model: is it possible? | 2003 Jan 31 |
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| Review article: clinical significance of mucosal-protective agents: acid, inflammation, carcinogenesis and rebamipide. | 2003 Jul |
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| Effects of rebamipide, a gastro-protective drug on the Helicobacter pylori status and inflammation in the gastric mucosa of patients with gastric ulcer: a randomized double-blind placebo-controlled multicentre trial. | 2003 Jul |
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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 protective effect of rebamipide on paracellular permeability of rat gastric epithelial cells. | 2003 Jul |
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| Gastric restitution is inhibited by dexamethasone, which is reversed by hepatocyte growth factor and rebamipide. | 2003 Jul |
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| Effect of rebamipide on prostaglandin receptors-mediated increase of inflammatory cytokine production by macrophages. | 2003 Jul |
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| Expression of midkine and receptor-like protein tyrosine phosphatase (RPTP)-beta genes in the rat stomach and the influence of rebamipide. | 2003 Jul |
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| Interaction of leptin with gastric myofibroblast transdifferentiation in Helicobacter pylori-infected Mongolian gerbils: the effect of rebamipide. | 2003 Jul |
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| The specific expression of hypoxia inducible factor-1alpha in human gastric mucosa induced by nonsteroidal anti-inflammatory drugs. | 2003 Jul |
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| Rebamipide binds to iNOS-positive cells in acetic acid-treated but not in ethanol-treated rat gastric mucosa. | 2003 Jul |
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| The effect of rebamipide on Helicobacter pylori extract-mediated changes of gene expression in gastric epithelial cells. | 2003 Jul |
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| Review article: rebamipide and the digestive epithelial barrier. | 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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| Review article: the role of rebamipide in the management of inflammatory disease of the gastrointestinal tract. | 2003 Jul |
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| Comparison of the effects of rebamipide with those of cimetidine on chronic gastritis associated with Helicobacter pylori in Mongolian gerbils. | 2003 Jul |
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| Cytoprotective effects of rebamipide and carteolol hydrochloride against ultraviolet B-induced corneal damage in mice. | 2003 Jul |
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| Free radical scavenger effect of rebamipide in sperm processing and cryopreservation. | 2003 Sep |
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| Protective effect of intra-rectal administration of rebamipide on dextran sulfate sodium-induced rat colitis. | 2004 |
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| Mechanism of hydroxyl radical scavenging by rebamipide: identification of mono-hydroxylated rebamipide as a major reaction product. | 2004 May |
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| COX-1 and COX-2 conversely promote and suppress ischemia-reperfusion gastric injury in mice. | 2005 Aug |
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| Rebamipide inhibits gastric cancer growth by targeting survivin and Aurora-B. | 2005 Aug 19 |
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| NADPH oxidase mediates interleukin-6 expression in cerulein-stimulated pancreatic acinar cells. | 2005 Jul |
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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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| Direct autoradiographic evidence that rebamipide interacts with neutrophils in dextran sulfate sodium induced colitis in rats. | 2005 Oct |
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| Rebamipide, a gastro-protective drug, inhibits indomethacin-induced apoptosis in cultured rat gastric mucosal cells: association with the inhibition of growth arrest and DNA damage-induced 45 alpha expression. | 2005 Oct |
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| A pilot study to evaluate a new combination therapy for gastric ulcer: Helicobacter pylori eradication therapy followed by gastroprotective treatment with rebamipide. | 2006 Jan |
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| Ambroxol for the prevention of acute upper respiratory disease. | 2006 Jun |
|
| The inhibitory effects of rebamipide on cigarette smoke-induced airway mucin production. | 2006 Mar |
Patents
Sample Use Guides
100 mg tid, in the morning, evening and before bedtime.
Route of Administration:
Oral
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WHO-ATC |
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)
