Calcipotriol

Calcipotriol
	File:Calcipotriol.svg
Clinical data
Pregnancy; category	B3 (Au), C (US);
Routes of; administration	Topical
ATC code	D05AX02 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only) ; US: ℞-only ;
Pharmacokinetic data
Bioavailability	5 to 6%
Metabolism	Hepatic
Excretion	Biliary
Identifiers
	IUPAC name (1R,3S)-5-[2-[(1R,3aR,7aS)-1-[(2S)-5-; cyclopropyl-5-hydroxy-pent-3-en-2-yl]-; 7a-methyl-2,3,3a,5,6,7-hexahydro-1H-; inden-4-ylidene]ethylidene]-4-methylidene-; cyclohexane-1,3-diol;
CAS Number	112965-21-6;
PubChem CID	443875;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C27H40O3
Molar mass	412.605 g/mol

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®.

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, kindney, 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.

Usage and Efficacy

Available as a cream, ointment or scalp solution (50mcg/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]

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 Dovobet®.

References

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

External links

Leo Pharmaceuticals Product Monograph- Detailed information from the manufacturers, includes the blood testing recommendation (.pdf document).

Calcipotriene information - U.S. NLM/NIH

Template:Pharma-stub Template:Antipsoriatics

[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. McCraw-Hill, 2006. p. 1664. p. 1704-5.

[4] Hardman et al. Hypercalcemia associated with calcipotriol (DOVONEX) treatment. Br Med J., 1993, 306:896.

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