1728. Camostat

Nomenclature

CAS number: 59721-28-7
4-[[4-[(Aminoiminomethyl)amino]benzoyl]oxy]benzeneacetic acid 2-(dimethylamino)-2-oxoethyl ester; N,N-dimethylcarbamoylmethyl-p-(p-guanidinobenzoyloxy)phenylacetate.
C20H22N4O5; mol wt 398.41.
C 60.29%, H 5.57%, N 14.06%, O 20.08%.

Description and references

Orally active, non-peptide proteolytic enzyme inhibitor with anti-trypsin and anti-plasmin activities, related structurally to gabexate, q.v. Prepn: S. Fujii et al., DE 2548886; eidem, US 4021472 (1976, 1977 both to Ono). Enzyme inhibition study: Y. Tamura et al., Biochim. Biophys. Acta 484, 417 (1977). Inhibition of exptl tumors in mice: M. Ohkoshi, Gann 72, 959 (1981), C.A. 96, 97304v (1982); M. Ohkoshi, S. Fujii, ibid. 73, 108 (1982), C.A. 96, 155182s (1982). Prevention of acute exptl pancreatitis: S. Takasugi et al., Digestion 24, 36 (1982). Absorption and excretion: S. Hiraku et al., Iyakuhin Kenkyu 13, 756 (1982), C.A. 97, 120038t (1982).

Chemical structure

Derivative

Methanesulfonate.

Nomenclature

CAS number: 59721-29-8
Camostat mesylate; FOY-305; Foipan (Ono).
C20H22N4O5.CH3SO3H; mol wt 494.52.
C 51.00%, H 5.30%, N 11.33%, O 25.88%, S 6.48%.

Properties

Solid from methanol/ether, mp 150-155°. Sol in water.

Therapeutic Category

Protease inhibitor.

Keywords

Protease Inhibitor