6355. Naftifine

Nomenclature

CAS number: 65472-88-0
(E)-N-Methyl-N-(3-phenyl-2-propenyl)-1-naphthalenemethanamine; (E)-N-cinnamyl-N-methyl-1-naphthalenemethylamine; N-methyl-N-(1-naphthylmethyl)-3-phenylpropen-1-amine; naftifungin.
C21H21N; mol wt 287.40.
C 87.76%, H 7.36%, N 4.87%.

Description and references

Antimycotic allylamine. Prepn: D. Berney, BE 853976; idem, US 4282251 (1977, 1981 both to Sandoz); A. Blade Fond, E. Mendoza-Villela, ES 504432 (1982 to Lab. Frumtost-Prem S.A.), C.A. 99, 38173r (1983); H. Loibner et al., Tetrahedron Lett. 25, 2535 (1984). In vitro activity against dermatophytes and Candida spp: A. Georgopoulos et al., Antimicrob. Agents Chemother. 19, 386 (1981). Morphological changes induced in Trichophyton mentagrophytes: J. C. Meingassner et al., J. Invest. Dermatol. 77, 444 (1981). Specific inhibitor of squalene epoxidase, a key enzyme in fungal ergosterol biosynthesis: F. Paltauf et al., Biochim. Biophys. Acta 712, 268 (1982); N. S. Ryder, Antimicrob. Agents Chemother. 25, 483 (1984). HPLC determn in human plasma and urine: F. Schatz, H. Haberl, Arzneim.-Forsch. 36, 1850 (1986). Clinical trials in dermatophytosis: U. Ganzinger et al., Clin. Trials J. 19, 342 (1982).

Chemical structure

Properties

Colorless, viscous oil, bp0.015 torr 162-167°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 65473-14-5
AW-105-843; SN-105-843; Exoderil (Rentschler); Naftin (Allergan); Suadian (Schering AG).
C21H21N.HCl; mol wt 323.86.
C 77.88%, H 6.85%, N 4.32%, Cl 10.95%.

Properties

mp 177° (from propanol).

Therapeutic Category

Antifungal (topical).

Keywords

Antifungal (Synthetic); Allylamines