1641. Calcipotriene

Nomenclature

CAS number: 112965-21-6
(1α,3β,5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1,3,24-triol; (1S,1′E,3R,5Z,7E,20R)-9,10-seco-20-(3′-cyclopropyl-3′-hydroxyprop-1′-enyl)-1,3-dihydroxypregna-5,7,10(19)-triene; calcipotriol; MC-903; Daivonex (Leo Pharm); Dovonex (Westwood-Squibb); Psorcutan (Schering AG).
C27H40O3; mol wt 412.60.
C 78.60%, H 9.77%, O 11.63%.

Description and references

Vitamin D3 analog with low calcemic activity. Prepn: M. J. Calverley, E. T. Binderup, WO 8700834; eidem, US 4866048 (1987, 1989 both to Leo Pharm.); M. J. Calverley, Tetrahedron 43, 4609 (1987). Pharmacology: L. Binderup, E. Bramm, Biochem. Pharmacol. 37, 889 (1988); P. J. Marie et al., Bone 11, 171 (1990). Receptor binding: T. Valaja et al., Biochem. Pharmacol. 40, 1827 (1990). Review of clinical trials in psoriasis: D. M. Ashcroft et al., Br. Med. J. 320, 963-967 (2000).

Chemical structure

Properties

Crystals from methyl formate, mp 166-168°. uv max (96% ethanol): 264 nm (ε 17200).

Therapeutic Category

Antipsoriatic.

Keywords

Antipsoriatic; Vitamin/Vitamin Source; Vitamin D