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 |
|---|---|---|---|
Target ID: CHEMBL2096907 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28011266 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Mucosta Approved UseUnknown |
|||
| Primary | Mucosta Approved UseUnknown |
|||
| Primary | Mucosta Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.96 ng/mL |
2 drop single, ocular dose: 2 drop route of administration: Ocular experiment type: SINGLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1 ng/mL |
2 drop single, ocular dose: 2 drop route of administration: Ocular experiment type: SINGLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
0.79 ng/mL |
2 drop single, ocular dose: 2 drop route of administration: Ocular experiment type: SINGLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.18 ng/mL |
2 drop 4 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1.66 ng/mL |
2 drop 4 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.13 ng/mL |
2 drop 4 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.39 ng/mL |
2 drop 4 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.19 ng/mL |
2 drop 4 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
218.12 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20110013/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
REBAMIPIDE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.45 ng × h/mL |
2 drop single, ocular dose: 2 drop route of administration: Ocular experiment type: SINGLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.71 ng × h/mL |
2 drop single, ocular dose: 2 drop route of administration: Ocular experiment type: SINGLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.55 ng × h/mL |
2 drop single, ocular dose: 2 drop route of administration: Ocular experiment type: SINGLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
10.3 ng × h/mL |
2 drop 4 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
13.48 ng × h/mL |
2 drop 4 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
851.68 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20110013/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
REBAMIPIDE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
10.26 h |
2 drop single, ocular dose: 2 drop route of administration: Ocular experiment type: SINGLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.64 h |
2 drop single, ocular dose: 2 drop route of administration: Ocular experiment type: SINGLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
11.34 h |
2 drop single, ocular dose: 2 drop route of administration: Ocular experiment type: SINGLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.19 h |
2 drop 4 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
10.64 h |
2 drop 4 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered: |
REBAMIPIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1.96 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20110013/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
REBAMIPIDE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.4% |
REBAMIPIDE plasma | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
200 mg 3 times / day multiple, oral Higher than recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Dizziness... AEs leading to discontinuation/dose reduction: Dizziness (grade 1, 0.44%) Sources: |
150 mg 2 times / day multiple, oral Studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Dizziness | grade 1, 0.44% Disc. AE |
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no [IC50 6800 uM] | ||||
| no [Inhibition 50 uM] | ||||
| no [Inhibition 50 uM] | ||||
| no [Inhibition 50 uM] | ||||
| no [Inhibition 50 uM] | ||||
| no [Inhibition 50 uM] | ||||
Page: 90.0 |
no | |||
Page: 7.0 |
no | |||
Page: 128.0 |
no | |||
Page: 149.0 |
no | |||
| yes [Inhibition 10 uM] | ||||
| yes [Inhibition 10 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| yes [Km 1010 uM] | ||||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 40.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Preventive effects of rebamipide on NSAID-induced gastric mucosal injury and reduction of gastric mucosal blood flow in healthy volunteers. | 2007-08 |
|
| [Safe improvement of drug absorption by combinatorial use of sodium laurate with amino acids: cytoprotection by amino acids and its mechanisms]. | 2007-04 |
|
| Rebamipide contributes to reducing adverse effects of long-term administration of omeprazole in rats. | 2007-04 |
|
| Rebamipide enema therapy as a treatment for patients with active distal ulcerative colitis. | 2007-02 |
|
| Ileal cancer and erosions in the small intestine revealed by capsule endoscopy. | 2007-02 |
|
| Effect of rebamipide on the colonic barrier in interleukin-10-deficient mice. | 2007-01 |
|
| Rebamipide inhibits gastric cancer cell growth. | 2007-01 |
|
| 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). | 2006-12 |
|
| Effect of a gastro-protective agent, rebamipide, on symptom improvement in patients with functional dyspepsia: a double-blind placebo-controlled study in Japan. | 2006-12 |
|
| Importance of bile acids for novel oral absorption system containing polyamines to improve intestinal absorption. | 2006-10-10 |
|
| [Case of drug-induced lung injury due to Rebamipide]. | 2006-10 |
|
| Ambroxol for the prevention of acute upper respiratory disease. | 2006-06 |
|
| OPC-12759 increases proliferation of cultured rat conjunctival goblet cells. | 2006-06 |
|
| Novel oral formulation safely improving intestinal absorption of poorly absorbable drugs: utilization of polyamines and bile acids. | 2006-03-10 |
|
| The inhibitory effects of rebamipide on cigarette smoke-induced airway mucin production. | 2006-03 |
|
| Optimization of suppository preparation containing sodium laurate and taurine that can safely improve rectal absorption of rebamipide. | 2006-02 |
|
| Successful treatment of severe pouchitis with rebamipide refractory to antibiotics and corticosteroids: a case report. | 2006-01-28 |
|
| A pilot study to evaluate a new combination therapy for gastric ulcer: Helicobacter pylori eradication therapy followed by gastroprotective treatment with rebamipide. | 2006-01 |
|
| Oxidative stress involvement and gene expression in indomethacin-induced gastropathy. | 2006 |
|
| Therapeutic effect of DA-9601 on chronic reflux gastritis induced by sodium taurocholate in rats. | 2005-12-21 |
|
| Efficacy of rebamipide enemas in active distal ulcerative colitis and proctitis: a prospective study report. | 2005-12 |
|
| Radical scavengers: a remedy for presbyacusis. A pilot study. | 2005-12 |
|
| [Quality of ulcer healing and rebamipide]. | 2005-11 |
|
| Prevention by rebamipide of acute reflux esophagitis in rats. | 2005-10 |
|
| Rebamipide reduces recurrence of experimental gastric ulcers: role of free radicals and neutrophils. | 2005-10 |
|
| Rebamipide reduces indomethacin-induced gastric injury in mice via down-regulation of ICAM-1 expression. | 2005-10 |
|
| Rebamipide significantly inhibits indomethacin-induced mitochondrial damage, lipid peroxidation, and apoptosis in gastric epithelial RGM-1 cells. | 2005-10 |
|
| Gastro-protective agent rebamipide induces cyclooxygenease-2 (COX-2) in gastric epithelial cells. | 2005-10 |
|
| Rebamipide reduces delay in gastric ulcer healing in cyclooxygenase-2-deficient mice. | 2005-10 |
|
| Rebamipide decreases the susceptibility of gastric mucosa to acid-induced injury in rats by inhibiting neutrophil activation. | 2005-10 |
|
| 15th anniversary of rebamipide: looking ahead to the new mechanisms and new applications. | 2005-10 |
|
| Rebamipide enema is effective for treatment of experimental dextran sulfate sodium induced colitis in rats. | 2005-10 |
|
| Rebamipide enemas-new effective treatment for patients with corticosteroid dependent or resistant ulcerative colitis. | 2005-10 |
|
| Direct autoradiographic evidence that rebamipide interacts with neutrophils in dextran sulfate sodium induced colitis in rats. | 2005-10 |
|
| 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. | 2005-10 |
|
| Rebamipide inhibits gastric cancer growth by targeting survivin and Aurora-B. | 2005-08-19 |
|
| COX-1 and COX-2 conversely promote and suppress ischemia-reperfusion gastric injury in mice. | 2005-08 |
|
| NADPH oxidase mediates interleukin-6 expression in cerulein-stimulated pancreatic acinar cells. | 2005-07 |
|
| [Enema therapy for ulcerative colitis patients]. | 2005-05 |
|
| Pharmacological characterization of rebamipide: its cholecystokinin CCK1 receptor binding profile and effects on Ca2+ mobilization and amylase release in rat pancreatic acinar cells. | 2004-11-28 |
|
| Development of suppository formulation safely improving rectal absorption of rebamipide, a poorly absorbable drug, by utilizing sodium laurate and taurine. | 2004-09-14 |
|
| Oral absorption and pharmacokinetics of rebamipide and rebamipide lysinate in rats. | 2004-09 |
|
| Rebamipide increases the amount of mucin-like substances on the conjunctiva and cornea in the N-acetylcysteine-treated in vivo model. | 2004-08 |
|
| Mechanism of hydroxyl radical scavenging by rebamipide: identification of mono-hydroxylated rebamipide as a major reaction product. | 2004-05 |
|
| Preventive effect of the flavonoid, wogonin, against ethanol-induced gastric mucosal damage in rats. | 2004-03 |
|
| Rebamipide activates genes encoding angiogenic growth factors and Cox2 and stimulates angiogenesis: a key to its ulcer healing action? | 2004-02 |
|
| Protective effect of intra-rectal administration of rebamipide on dextran sulfate sodium-induced rat colitis. | 2004 |
|
| Study of inhibition of CYP2A6 by some drugs derived from quinoline. | 2003-12 |
|
| [Agranulocytosis due to anti-tuberculosis drugs including isoniazid (INH) and rifampicin (RFP)--a report of four cases and review of the literature]. | 2003-11 |
|
| Bioequivalence of rebamipide granules and tablets in healthy adult male volunteers. | 2003 |
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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WHO-ATC |
A02BX14
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NCI_THESAURUS |
C29701
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LR583V32ZR
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C29852
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Rebamipide
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SUB10267MIG
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ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)