Calcipotriol
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Calcipotriol
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| Systematic (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 |
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| Identifiers | |
| CAS number | |
| ATC code | D05 |
| PubChem | |
| Chemical data | |
| Formula | C27H40O3 |
| Mol. mass | 412.605 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 5 to 6% |
| Metabolism | Hepatic |
| Half life | ? |
| Excretion | Biliary |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| Routes | Topical |
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.
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[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, 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.
[edit] 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]
[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.
[edit] 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.
[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
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