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

• ChemBase ID: 154104
• Molecular Formular: C19H17ClN2O5
• Molecular Mass: 388.80168
• Monoisotopic Mass: 388.08259933
• SMILES: c1ccc2c(c1)c(cc(=O)[nH]2)CC(C(=O)O)NC(=O)c1ccc(cc1)Cl.O
• Canonical SMILES: Clc1ccc(cc1)C(=O)NC(C(=O)O)Cc1cc(=O)[nH]c2c1cccc2.O
• InChI: InChI=1S/C19H15ClN2O4.H2O/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);1H2
• InChIKey: WQRHVBKNEDPECA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4-chlorophenyl)formamido]-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoic acid hydrate
• IUPAC Traditional name: rebamipide hydrate
• Synonyms: α-[(4-Chlorobenzoyl)amino]-1,2-dihydro-2-oxo-4-quinolinepropanoic acid hydrate; Mucosta hydrate; OPC 12759 hydrate; Proamipide hydrate; Rebamipide hydrate

Database IDs

• CAS Number: 90098-04-7(anhydrous)
• MDL Number: MFCD11114396
• PubChem SID: 162248243
• PubChem CID: 67351561

CALCULATED PROPERTIES

• Acid pKa: 3.518527
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.7906722
• LogD (pH = 7.4): -0.6052261
• Log P: 2.7645504
• Molar Refractivity: 98.4974 cm^3
• Polarizability: 36.540874 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL
• Apperance: white powder

Safety Information

• RTECS: VC2518500
• German water hazard class: 3
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H15ClN2O4 · xH2O

DETAILS

Sigma Aldrich - R5655

Biochem/physiol Actions
Rebamipide is an anti-ulcer agent with free-radical scavenging and anti-inflammatory effects. It has been used for mucosal protection, healing of gastroduodenal ulcers, and treatment of gastritis. It works by enhancing mucosal defense, scavenging free radicals, and temporarily activating COX-2 genes. Rebamipide significantly reduced ulcerogenesis and maintained mucosal superoxide dismutase (SOD) activity. It has also been used for the treatment of Behçet′s disease. Rebamipide may be involved in a noval mechanism to enhance tear secretion and increase mucin levels covering conjunctiva and cornea.