Rebamipide

DRACPC ID  DRACPC0090

Active Ingredients   Rebamipide

Description  A quinolinone derivative with anti-ulcer and anti-inflammatory activities. Rebamipide induces cyclooxygenase 2 (COX2) synthesis which results in an increase in endogenous prostaglandin synthesis in the gastric mucosa. This agent also inhibits H. pylori-induced production of tumor necrosis factor (TNF) alpha and subsequent inflammation of the gastric mucosa. In addition, rebamipide scavenges oxygen-derived free radicals that potentially cause mucosal injury, and stimulates prostaglandin EP4 receptor gene expression followed by mucous secretion, thereby enhancing the gastric mucosal defense.

Synonyms  alpha-[(4-Chlorobenzoyl)amino]-1,2-dihydro-2-oxo-4-quinolinepropanoic Acid; OPC 12759; Rebamipide

Type  Small Molecule

Disease  Early Gastric Cancer, Stomach Ulcer, Keratoconjunctivitis Sicca, Gastric Adenoma

Classification

  

Amino acid and derivative

Structure Information


Molecular Formula  C19H15ClN2O4

Molecular Weight  370.8

Active Sequence  Not available

Sequence Length  Not available

Modification  Not available

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  2-[(4-chlorophenyl)formamido]-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoic acid

InChI  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)

InChI_Key ALLWOAVDORUJLA-UHFFFAOYSA-N

SMILES  O=C(O)C(NC(C1=CC=C(Cl)C=C1)=O)CC2=CC(NC3=C2C=CC=C3)=O

External Codes


PubChem CID  5042

DrugBank Accession Number  DB11656

NCI Thesaurus Code  C29852  

UNII  LR583V32ZR   GSRS

CAS  90098-04-7



Drug approval


Drug indication
    Rebamipide has been investigated for the treatment of Stomach Ulcer, Keratoconjunctivitis Sicca, and Gastric Adenoma and Early Gastric Cancer.

    The drug is not approved.

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT02085460 A Multicenter, Randomized, Double-blind, Placebo-controlled, Parallel-group Phase 2 Trial of Rebamipide Liquid to Determine the Effective Dose for Prevention of Chemoradiotherapy-induced Oral Mucositis in Patients With Head and Neck Cancer Head and Neck Cancer Phase 2 Treatment
NCT02243618 The Effect of Proton Pump Inhibitor and Polaprezinc Combination Therapy for Healing of Endoscopic Submucosal Dissection-induced Ulcer Gastric Adenoma; Early Gastric Cancer Not Applicable Treatment
NCT03608761 Comparison Between Rebamipide 2% Versus Autologous Serum in the Treatement of the Moderate to Severe Dry Eye Associate With Sjögren Syndrome. Pilot, Crossed, Controled, Randomized And Open Study Dry Eye Syndromes; Sjögren Syndrome Phase 4 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





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