5515. Liranaftate

Nomenclature

CAS number: 88678-31-3
(6-Methoxy-2-pyridinyl)methylcarbamothioic acid O-(5,6,7,8-tetrahydro-2-naphthalenyl) ester; O-5,6,7,8-tetrahydro-2-naphthyl N-(6-methoxy-2-pyridyl)-N-methylthiocarbamate; piritetrate; M-732; Zefnart (Tosoh).
C18H20N2O2S; mol wt 328.43.
C 65.83%, H 6.14%, N 8.53%, O 9.74%, S 9.76%.

Description and references

Squalene epoxidase inhibitor. Prepn: BE 897021; T. Takematsu et al., US 4554012 (1983, 1985 both to Toyo Soda Manufacturing Co., Ltd.). Mode of action study: T. Morita et al., J. Med. Vet. Mycol. 27, 17 (1989). Antifungal spectrum: K. Iwata et al., Antimicrob. Agents Chemother. 33, 2118 (1989). Physicochemical properties and stability: H. Awano et al., Iyakuhin Kenkyu 23, 558 (1992).

Chemical structure

Properties

White crystalline powder, mp 98.5-99.5°. Soly (ml/g): acetone 10; chloroform 2; dehydrated ethanol 152; dichloromethane 2; ether 21; hexane 233; methanol 175; water >10000. Soly (mg/l): 0.10 (distilled water); 0.07 (buffer pH 1); 0.08 (buffer pH 4); 0.07 (buffer pH 7); 0.08 (buffer pH 11). Sol in benzene, dimethyl sulfoxide, N,N-dimethylformamide.

Therapeutic Category

Antifungal.

Keywords

Antifungal (Synthetic); Thiocarbamates