8124. Rebamipide

Nomenclature

CAS number: 90098-04-7
α-[(4-Chlorobenzoyl)amino]-1,2-dihydro-2-oxo-4-quinolinepropanoic acid; (±)-α-(p-chlorobenzamido)-1,2-dihydro-2-oxo-4-quinolinepropionic acid; 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid; proamipide; OPC-12759; Mucosta (Otsuka).
C19H15ClN2O4; mol wt 370.79.
C 61.55%, H 4.08%, Cl 9.56%, N 7.56%, O 17.26%.

Description and 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).

Chemical structure

Properties

White powder from DMF-water, mp 288-290° (dec) as hemihydrate.

Derivative

(-)-Form.

Properties

Colorless needles from DMF, mp 305-306° (dec). [α]D20 -116.7° (c = 1.0 in DMF).

Derivative

(+)-Form.

Properties

Colorless needles from DMF, mp 305-306° (dec). [α]D20 +116.9° (c = 1.0 in DMF).

Therapeutic Category

Antiulcerative.

Keywords

Antiulcerative; Cytoprotectant (Gastric)