Calcipotriol

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-methylidenecyclohexane-1,3-diol
Identifiers
CAS number	112965-21-6
ATC code	D05AX02
PubChem	5288783
ChemSpider	4450880
Chemical data
Formula	C27H40O3
Mol. mass	412.605 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	5 to 6%
Metabolism	Hepatic
Half life	?
Excretion	Biliary
Therapeutic considerations
Pregnancy cat.	B3 (Au), C (US)
Legal status	POM(UK) ℞-only(US)
Routes	Topical
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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 or Daivonex.

Contents 1 Mechanism 2 Usage and efficacy 3 Side effects 4 References 5 External links

[edit] Mechanism

The efficacy of calcipotriol in the treatment of psoriasis was first noticed by the observation of patients receiving various forms of Vitamin D in an osteoporosis study. Unexpectedly, a patient's psoriasis lesions dramatically disappeared. ^[1]

The precise mechanism of calcipotriol in remitting psoriasis is not well-understood. However, it has been shown to have comparable affinity with calcitriol (Vit D) for the Vitamin D receptor, while being less than 1% as active as the calcitriol in regulating calcium metabolism. The Vitamin D receptor (VDR) belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kidney, and T cells of the immune system. T cells are known to play a role in psoriasis, and it is thought that the binding of calcipotriol to the VDR modulates the T cells gene transcription of cell differentiation and proliferation related genes.

[edit] Usage and efficacy

Available as a cream, ointment or scalp solution (50 µg/mL), Calcipotriol is applied twice daily to plaque psoriasis on the body or scalp, but not the face. Improvement is usually detectable within 2 weeks. Most patients show some improvement, slightly more so than is seen with the use of corticosteroids alone. Tachyphylaxis does not occur, an improvement over glucocorticoid therapy.^[2]

[edit] Side effects

Calcipotriol has been shown in clinical trials to have an excellent safety profile. ^[3] Reports of hypercalcemia are rare.^[4]

It is also available in combination with the synthetic glucocorticoid betamethasone under the trade name Taclonex, Dovobet or Daivobet.

[edit] References

1. ^ Morimoto, S., Kumahara, Y. A patient with psoriasis cured by 1-α-hydroxyvitamin D₃. Med. J. Osaka Univ., 1985, 35:51-54
2. ^ Kragbelle, K. Treatment of psoriasis with calcipotriol and other Vitamin D analogues. J. Am. Acad. Dermatol., 1992, 27:1001-1008.
3. ^ Brunton, Laurence. Goodman and Gilman's The Pharmacological Basis of Therapeutics, 11th ed. McGraw-Hill, 2006. p. 1664. p. 1704-5.
4. ^ Hardman et al. Hypercalcemia associated with calcipotriol (DOVONEX) treatment. Br Med J., 1993, 306:896.

[edit] External links

• Leo Pharmaceuticals Product Monograph- Detailed information from the manufacturers, includes the blood testing recommendation (.pdf document).
• Calcipotriene information - U.S. NLM/NIH

v • d • e Antipsoriatics (D05) Topical Tars Tar Antracens Dithranol Psoralens Trioxysalen - Methoxsalen Other Fumaric acid - vitamin D (Calcipotriol, Calcitriol, Tacalcitol) - Tazarotene Systemic Psoralens Trioxysalen - Methoxsalen - Bergapten Retinoids Etretinate - Acitretin

v • d • e Vitamins (A11) Fat soluble A Retinol · β-Carotene · Tretinoin · α-Carotene D D2 (Ergosterol, Ergocalciferol)  · D3 (7-Dehydrocholesterol, Previtamin D3, Cholecalciferol, 25-hydroxycholecalciferol, Calcitriol (1,25-dihydroxycholecalciferol), Calcitroic acid) D4 (Dihydroergocalciferol)  · D5  · D analogues (Dihydrotachysterol, Calcipotriol, Tacalcitol, Paricalcitol) E Tocopherol (Alpha, Beta, Gamma, Delta) · Tocotrienol · Tocofersolan K Naphthoquinone · Phylloquinone/K1 · Menatetrenone/K2 · Menadione/K3 Water soluble B B1 (Thiamine) · B2 (Riboflavin) · B3 (Niacin, Nicotinamide) · B5 (Pantothenic acid, Dexpanthenol, Pantethine) · B6 (Pyridoxine, Pyridoxal phosphate, Pyridoxamine) B7 (Biotin) · B9 (Folic acid, Dihydrofolic acid, Folinic acid) · B12 (Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide)  · Choline C Ascorbic acid  · Dehydroascorbic acid see also: enzyme cofactors, enzymes, Multivitamins

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