CAS No 90098-04-7 , 2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1H-quinolin-4-yl)propanoic acid

Title: Rebamipide
CAS Registry Number: 90098-04-7
CAS Name: a-[(4-Chlorobenzoyl)amino]-1,2-dihydro-2-oxo-4-quinolinepropanoic acid
Synonyms: (±)-a-(p-chlorobenzamido)-1,2-dihydro-2-oxo-4-quinolinepropionic acid; 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid; proamipide
Manufacturers' Codes: OPC-12759
Trademarks: Mucosta (Otsuka)
Molecular Formula: C19H15ClN2O4
Molecular Weight: 370.79
Percent Composition: C 61.55%, H 4.08%, Cl 9.56%, N 7.56%, O 17.26%
Literature References: Gastric cytoprotectant. Prepn: M. Uchida et al., DE 3324034; eidem, US 4578381; (1984, 1986 both to Otsuka). Synthesis and pharmacology: M. Uchida et al., Chem. Pharm. Bull. 33, 3775 (1985); of enantiomers: eidem, ibid. 35, 853 (1987). Antiulcer activity in rats: K. Yamasaki et al., Eur. J. Pharmacol. 142, 23 (1987); K. Yamasaki et al., Jpn. J. Pharmacol. 49, 441 (1989). HPLC determn in plasma and urine: Y. Shioya, T. Shimizu, J. Chromatogr. 434, 283 (1988).
Properties: White powder from DMF-water, mp 288-290° (dec) as hemihydrate.
Melting point: mp 288-290° (dec) as hemihydrate
 
Derivative Type: (-)-Form
Properties: Colorless needles from DMF, mp 305-306° (dec). [a]D20 -116.7° (c = 1.0 in DMF).
Melting point: mp 305-306° (dec)
Optical Rotation: [a]D20 -116.7° (c = 1.0 in DMF)
 
Derivative Type: (+)-Form
Properties: Colorless needles from DMF, mp 305-306° (dec). [a]D20 +116.9° (c = 1.0 in DMF).
Melting point: mp 305-306° (dec)
Optical Rotation: [a]D20 +116.9° (c = 1.0 in DMF)
 
Therap-Cat: Antiulcerative.
Keywords: Antiulcerative; Cytoprotectant (Gastric).