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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 of REBAMIPIDE

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)

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Mucosta

Approved Use

Unknown
Primary
Mucosta

Approved Use

Unknown
Primary
Mucosta

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
1.4%
REBAMIPIDE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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]
no
no
no
no
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
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
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
INN   JAN   MI   WHO-DD  
INN  
Official Name English
MUCOSTA
Preferred 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
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
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
NCI_THESAURUS C29701
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
Code System Code Type Description
IUPHAR
871
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
FDA UNII
LR583V32ZR
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
CAS
90098-04-7
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
EPA CompTox
DTXSID8045937
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
NCI_THESAURUS
C29852
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
WIKIPEDIA
Rebamipide
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
EVMPD
SUB10267MIG
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
DRUG BANK
DB11656
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
MESH
C052785
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
DRUG CENTRAL
2360
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
PUBCHEM
5042
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
ChEMBL
CHEMBL1697771
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
MERCK INDEX
m9512
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY Merck Index
CAS
139344-42-6
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SUPERSEDED
CAS
111911-87-6
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
SUPERSEDED
INN
6454
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
NSC
758955
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY
SMS_ID
100000080803
Created by admin on Mon Mar 31 18:12:50 GMT 2025 , Edited by admin on Mon Mar 31 18:12:50 GMT 2025
PRIMARY