Calcipotriene

Title: Calcipotriene
CAS Registry Number: 112965-21-6
CAS Name: (1a,3b,5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1,3,24-triol
Additional Names: (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
Manufacturers' Codes: MC-903
Trademarks: Daivonex (Leo Pharm); Dovonex (Westwood-Squibb); Psorcutan (Schering AG)
Molecular Formula: C27H40O3
Molecular Weight: 412.60
Percent Composition: C 78.60%, H 9.77%, O 11.63%
Literature 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).
Properties: Crystals from methyl formate, mp 166-168°. uv max (96% ethanol): 264 nm (e 17200).
Melting point: mp 166-168°
Absorption maximum: uv max (96% ethanol): 264 nm (e 17200)
Therap-Cat: Antipsoriatic.
Keywords: Antipsoriatic; Vitamin/Vitamin Source; Vitamin D.
Calciseptine Calcitonin Calcium 2-Ethylbutanoate Calcium 3-Aurothio-2-propanol-1-sulfonate Calcium Acetate

Calcipotriol
Calcipotriol2DACS.svg
Systematic (IUPAC) name
(1R,3S,5E)-5-{2-[(1R,3aS,4Z,7aR)-1-[(2R,3E)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohyytyexane-1,3-diol
Clinical data
Trade names Daivobex, Dovobex, Sorilux
AHFS/Drugs.com monograph
MedlinePlus a608018
Pregnancy cat. B3 (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Topical
Pharmacokinetic data
Bioavailability 5 to 6%
Metabolism Hepatic
Excretion Biliary
Identifiers
CAS number 112965-21-6 YesY
ATC code D05AX02
PubChem CID 5288783
IUPHAR ligand 2778
DrugBank DB02300
ChemSpider 4450880 YesY
UNII 143NQ3779B YesY
KEGG D01125 YesY
ChEBI CHEBI:50749 YesY
ChEMBL CHEMBL100918 N
Chemical data
Formula C27H40O3 
Mol. mass 412.605 g/mol
 N (what is this?)  (verify)

Calcipotriol (INN) or calcipotriene (USAN) is a synthetic derivative of calcitriol or vitamin D. It is used in the treatment of psoriasis, marketed under the trade name "Dovonex" in the United States, "Daivonex" outside of North America, and "Psorcutan" in Germany. This medication is safe for long term application in psoriatic skin condition.