6350. Nafamostat

Nomenclature

CAS number: 81525-10-2
4-[(Aminoiminomethyl)amino]benzoic acid 6-(aminoiminomethyl)-2-naphthalenyl ester; 6-amidino-2-naphthyl-4-guanidinobenzoate; nafamstat.
C19H17N5O2; mol wt 347.37.
C 65.69%, H 4.93%, N 20.16%, O 9.21%.

Description and references

Non-peptide protease inhibitor. Prepn: S. Fujii et al., EP 48433; eidem, US 4454338 (1982, 1984 both to Torii & Co.); T. Aoyama et al., Chem. Pharm. Bull. 33, 1458 (1985). Inhibitory effects on trypsin, thrombin, kallikrein, plasmin and complement-mediated hemolysis: S. Fujii, Y. Hitomi, Biochim. Biophys. Acta 661, 342 (1981); T. Aoyama et al., Jpn. J. Pharmacol. 35, 203 (1984). Effect in experimental acute pancreatitis in rats: M. Iwaki et al., ibid. 41, 155 (1986). Spectrofluorometric determn in biological material: T. Aoyama et al., Chem. Pharm. Bull. 33, 2142 (1985). Clinical anti-complement activity: Y. Miyamoto et al., Trans. Am. Soc. Artif. Intern. Organs 31, 508 (1985).

Chemical structure

Derivative

Dimethanesulfonate.

Nomenclature

CAS number: 82956-11-4
Nafamostat mesylate; FUT-175; Futhan (Torii).
C19H17N5O2.2CH3SO3H; mol wt 539.58.
C 46.74%, H 4.67%, N 12.98%, O 23.72%, S 11.89%.

Properties

Crystals from ethyl ether, mp 217-220° (Fujii). Also reported as colorless powder from water, mp 260° (dec) (Aoyama).

Therapeutic Category

Enzyme inhibitor (protease).

Keywords

Protease Inhibitor