Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C25H26ClN3O5 |
| Molecular Weight | 483.944 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=CC=C(C=C1)C(=O)NC(CC2=CC(=O)NC3=CC=CC=C23)C(=O)OCCN4CCOCC4
InChI
InChIKey=BVZOVIJSRAGQLP-UHFFFAOYSA-N
InChI=1S/C25H26ClN3O5/c26-19-7-5-17(6-8-19)24(31)28-22(25(32)34-14-11-29-9-12-33-13-10-29)15-18-16-23(30)27-21-4-2-1-3-20(18)21/h1-8,16,22H,9-15H2,(H,27,30)(H,28,31)
| Molecular Formula | C25H26ClN3O5 |
| Molecular Weight | 483.944 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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 |
|---|---|---|
| Bioequivalence of rebamipide granules and tablets in healthy adult male volunteers. | 2003 |
|
| Study of inhibition of CYP2A6 by some drugs derived from quinoline. | 2003 Dec |
|
| [Agranulocytosis due to anti-tuberculosis drugs including isoniazid (INH) and rifampicin (RFP)--a report of four cases and review of the literature]. | 2003 Nov |
|
| Protective effect of intra-rectal administration of rebamipide on dextran sulfate sodium-induced rat colitis. | 2004 |
|
| Rebamipide increases the amount of mucin-like substances on the conjunctiva and cornea in the N-acetylcysteine-treated in vivo model. | 2004 Aug |
|
| Rebamipide activates genes encoding angiogenic growth factors and Cox2 and stimulates angiogenesis: a key to its ulcer healing action? | 2004 Feb |
|
| Preventive effect of the flavonoid, wogonin, against ethanol-induced gastric mucosal damage in rats. | 2004 Mar |
|
| Mechanism of hydroxyl radical scavenging by rebamipide: identification of mono-hydroxylated rebamipide as a major reaction product. | 2004 May |
|
| Pharmacological characterization of rebamipide: its cholecystokinin CCK1 receptor binding profile and effects on Ca2+ mobilization and amylase release in rat pancreatic acinar cells. | 2004 Nov 28 |
|
| Oral absorption and pharmacokinetics of rebamipide and rebamipide lysinate in rats. | 2004 Sep |
|
| Development of suppository formulation safely improving rectal absorption of rebamipide, a poorly absorbable drug, by utilizing sodium laurate and taurine. | 2004 Sep 14 |
|
| COX-1 and COX-2 conversely promote and suppress ischemia-reperfusion gastric injury in mice. | 2005 Aug |
|
| Rebamipide inhibits gastric cancer growth by targeting survivin and Aurora-B. | 2005 Aug 19 |
|
| Efficacy of rebamipide enemas in active distal ulcerative colitis and proctitis: a prospective study report. | 2005 Dec |
|
| Radical scavengers: a remedy for presbyacusis. A pilot study. | 2005 Dec |
|
| Therapeutic effect of DA-9601 on chronic reflux gastritis induced by sodium taurocholate in rats. | 2005 Dec 21 |
|
| NADPH oxidase mediates interleukin-6 expression in cerulein-stimulated pancreatic acinar cells. | 2005 Jul |
|
| [Enema therapy for ulcerative colitis patients]. | 2005 May |
|
| [Quality of ulcer healing and rebamipide]. | 2005 Nov |
|
| Prevention by rebamipide of acute reflux esophagitis in rats. | 2005 Oct |
|
| Rebamipide reduces recurrence of experimental gastric ulcers: role of free radicals and neutrophils. | 2005 Oct |
|
| Rebamipide reduces indomethacin-induced gastric injury in mice via down-regulation of ICAM-1 expression. | 2005 Oct |
|
| Rebamipide significantly inhibits indomethacin-induced mitochondrial damage, lipid peroxidation, and apoptosis in gastric epithelial RGM-1 cells. | 2005 Oct |
|
| Gastro-protective agent rebamipide induces cyclooxygenease-2 (COX-2) in gastric epithelial cells. | 2005 Oct |
|
| Rebamipide reduces delay in gastric ulcer healing in cyclooxygenase-2-deficient mice. | 2005 Oct |
|
| Rebamipide decreases the susceptibility of gastric mucosa to acid-induced injury in rats by inhibiting neutrophil activation. | 2005 Oct |
|
| 15th anniversary of rebamipide: looking ahead to the new mechanisms and new applications. | 2005 Oct |
|
| Rebamipide enema is effective for treatment of experimental dextran sulfate sodium induced colitis in rats. | 2005 Oct |
|
| Rebamipide enemas-new effective treatment for patients with corticosteroid dependent or resistant ulcerative colitis. | 2005 Oct |
|
| Direct autoradiographic evidence that rebamipide interacts with neutrophils in dextran sulfate sodium induced colitis in rats. | 2005 Oct |
|
| 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 |
|
| Oxidative stress involvement and gene expression in indomethacin-induced gastropathy. | 2006 |
|
| Assessing the efficacy of famotidine and rebamipide in the treatment of gastric mucosal lesions in patients receiving long-term NSAID therapy (FORCE--famotidine or rebamipide in comparison by endoscopy). | 2006 Dec |
|
| 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 |
|
| Optimization of suppository preparation containing sodium laurate and taurine that can safely improve rectal absorption of rebamipide. | 2006 Feb |
|
| A pilot study to evaluate a new combination therapy for gastric ulcer: Helicobacter pylori eradication therapy followed by gastroprotective treatment with rebamipide. | 2006 Jan |
|
| Successful treatment of severe pouchitis with rebamipide refractory to antibiotics and corticosteroids: a case report. | 2006 Jan 28 |
|
| Ambroxol for the prevention of acute upper respiratory disease. | 2006 Jun |
|
| OPC-12759 increases proliferation of cultured rat conjunctival goblet cells. | 2006 Jun |
|
| The inhibitory effects of rebamipide on cigarette smoke-induced airway mucin production. | 2006 Mar |
|
| Novel oral formulation safely improving intestinal absorption of poorly absorbable drugs: utilization of polyamines and bile acids. | 2006 Mar 10 |
|
| [Case of drug-induced lung injury due to Rebamipide]. | 2006 Oct |
|
| Importance of bile acids for novel oral absorption system containing polyamines to improve intestinal absorption. | 2006 Oct 10 |
|
| [Safe improvement of drug absorption by combinatorial use of sodium laurate with amino acids: cytoprotection by amino acids and its mechanisms]. | 2007 Apr |
|
| Rebamipide contributes to reducing adverse effects of long-term administration of omeprazole in rats. | 2007 Apr |
|
| Preventive effects of rebamipide on NSAID-induced gastric mucosal injury and reduction of gastric mucosal blood flow in healthy volunteers. | 2007 Aug |
|
| Rebamipide enema therapy as a treatment for patients with active distal ulcerative colitis. | 2007 Feb |
|
| Ileal cancer and erosions in the small intestine revealed by capsule endoscopy. | 2007 Feb |
|
| Effect of rebamipide on the colonic barrier in interleukin-10-deficient mice. | 2007 Jan |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 14:58:21 GMT 2023
by
admin
on
Sat Dec 16 14:58:21 GMT 2023
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| Record UNII |
1L45T26ZFA
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| Record Status |
Validated (UNII)
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| Record Version |
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1L45T26ZFA
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86296442
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300000018847
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C171745
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11084
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