573. Amorolfine

Nomenclature

CAS number: 78613-35-1
(2R,6S)-rel-4-[3-[4-(1,1-Dimethylpropyl)phenyl]-2-methylpropyl]-2,6-dimethylmorpholine; cis-4-[3-(4-tert-amylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine; (±)-cis-2,6-dimethyl-4-[2-methyl-3-(p-tert-pentylphenyl)propyl]morpholine; Ro-14-4767/000.
C21H35NO; mol wt 317.51.
C 79.44%, H 11.11%, N 4.41%, O 5.04%.

Description and references

Antimycotic morpholine derivative; inhibits fungal ergosterol biosynthesis. Prepn (unspec stereochem): A. Pfiffner, K. Bohnen, DE 2752096; A. Pfiffner, US 4202894 (1978, 1980 both to Hoffmann-La Roche); of cis-form: NL 8004537 (1980 to Hoffmann-La Roche). In vitro comparative antifungal spectrum: S. Shadomy et al., Sabouraudia 22, 7 (1984). Mechanism of action: A. Polak-Wyss et al., ibid. 23, 433 (1985); A. Polak, Ann. N.Y. Acad. Sci. 544, 221 (1988). LC determn in pharmaceutical formulations: M. A. Czech et al., J. Pharm. Biomed. Anal. 9, 1019 (1991). Series of articles on mode of action and clinical trials: Clin. Exp. Dermatol. 17, Suppl. 1, 1-70 (1992). Review of pharmacology and clinical efficacy: M. Haria, H. M. Bryson, Drugs 49, 103-120 (1995).

Chemical structure

Properties

bp0.1 120°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 78613-38-4
Ro-14-4767/002; Loceryl (Roche).
C21H35NO.HCl; mol wt 353.97.
C 71.26%, H 10.25%, N 3.96%, O 4.52%, Cl 10.02%.

Therapeutic Category

Antifungal (topical).

Keywords

Antifungal (Synthetic)