(5Z)-5-{2-[(4Z)-1-[(3E)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol

• ChemBase ID: 2046
• Molecular Formular: C27H40O3
• Molecular Mass: 412.6047
• Monoisotopic Mass: 412.29774514
• SMILES: CC(/C=C/C(O)C1CC1)C1CCC2/C(=C\C=C/3\CC(O)CC(O)C3=C)/CCCC12C
• Canonical SMILES: OC1CC(O)C(=C)/C(=C\C=C/2\CCCC3(C2CCC3C(/C=C/C(C2CC2)O)C)C)/C1
• InChI: InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7-,21-10-
• InChIKey: LWQQLNNNIPYSNX-FJGALDFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-5-{2-[(4Z)-1-[(3E)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• IUPAC Traditional name: calcipotriol
• Brand Name: Dovonex; Davonex
• Synonyms: Calcipotriene; Calcipotriol

Database IDs

• CAS Number: 112965-21-6
• PubChem SID: 160965501
• PubChem CID: 6376277

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.392874
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 3.8433506
• LogD (pH = 7.4): 3.8433506
• Log P: 3.843351
• Molar Refractivity: 125.4493 cm^3
• Polarizability: 48.449245 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.63
• LOG S: -4.49
• Solubility (Water): 1.35e-02 g/l

DETAILS

DrugBank - DB02300

• Drug Groups: approved; nutraceutical
• Description: Calcipotriol (INN) or calcipotriene (USAN) is a sythetic derivative of calcitriol or Vitamin D.
• Indication: For the treatment of moderate plaque psoriasis in adults.
• Pharmacology: Calcipotriene is a synthetic analog of vitamin D. In humans, the natural supply of vitamin D depends mainly on exposure to the ultraviolet rays of the sun for conversion of 7-dehydrocholesterol to vitamin D3 (cholecalciferol) in the skin.
• Toxicity: Topically applied calcipotriene can be absorbed in sufficient amounts to produce systemic effects. Elevated serum calcium has been observed with excessive use of calcipotriene.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Calcipotriene metabolism following systemic uptake is rapid, and occurs via a similar pathway to the natural hormone. The primary metabolites are much less potent than the parent compound.
• Absorption: Clinical studies with radiolabeled ointment indicate that approximately 6% (+3%, SD) of the applied dose of calcipotriene is absorbed systemically when the ointment is applied topically to psoriasis plaques or 5% (+2.6%, SO) when applied to normal skin.
• Elimination: The active form of the vitamin, 1,25-dihydroxy vitamin D3 (calcitriol), is known to be recycled via the liver and excreted in the bile. There is evidence that maternal 1,25-dihydroxy vitamin D3 (calcitriol) may enter the fetal circulation, but it is not known whether it is excreted in human milk.
• External Links: Wikipedia; RxList