13-08531. Sepimostat [Archived]

Nomenclature

CAS number: 103926-64-3
4-[(4,5-Dihydro-1H-imidazol-2-yl)amino]benzoic acid 6-(aminoiminomethyl)-2-naphthalenyl ester; 6-amidino-2-naphthyl p-(2-imidazolin-2-ylamino)benzoate.
C21H19N5O2; mol wt 373.41.
C 67.55%, H 5.13%, N 18.76%, O 8.57%.

Description and references

Nonpeptide serine protease inhibitor; structural analog of nafamostat. Prepn: S. Fujii et al., WO 8600893; eidem, US 4777182 (1986, 1988 both to Torii); T. Nakayama et al., Chem. Pharm. Bull. 41, 117 (1993). Enzyme inhibitory activity: M. Oda et al., Jpn. J. Pharmacol. 52, 23 (1990). Effects on exptl pancreatitis: H. Murakami et al., Arzneim.-Forsch. 40, 1352 (1990). HPLC determn in biological fluids: T. Marunaka et al., J. Chromatogr. 433, 177 (1988). Toxicity study: K. Terazawa et al., J. Toxicol. Sci. 17, Suppl. 4, 1 (1992).

Chemical structure

Derivative

Methanesulfonate.

Nomenclature

CAS number: 103926-82-5
Sepimostat mesylate; FUT-187; TO-187; Renofuthan (Torii).
C21H19N5O2.2CH3SO3H; mol wt 565.62.
C 48.84%, H 4.81%, N 12.38%, O 22.63%, S 11.34%.

Properties

Crystals from water-ethanol, mp 248-250°. Sol in water. LD50 in male, female mice, male, female rats (mg/kg): 39.4, 41.4, 21.8, 15.8 i.v.; 6284, 5492, 6799, 3343 s.c.; 4395, 3626, 4653, 3761 orally (Terazawa).

Therapeutic Category

Protease inhibitor.

Keywords

Protease Inhibitor

Status

This monograph has been retired and is no longer subject to revision or update.