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 | |
| Clinical data | |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a608018 |
| Pregnancy cat. | B3 (Au), C (US) |
| Legal status | POM (UK) ℞-only (US) |
| Routes | Topical |
| Pharmacokinetic data | |
| Bioavailability | 5 to 6% |
| Metabolism | Hepatic |
| Excretion | Biliary |
| Identifiers | |
| CAS number | 112965-21-6  |
| ATC code | D05AX02 |
| PubChem | CID 5288783 |
| DrugBank | DB02300 |
| ChemSpider | 4450880 |
| UNII | 143NQ3779B |
| KEGG | D01125 |
| ChEBI | CHEBI:50749 |
| ChEMBL | CHEMBL100918  |
| Chemical data | |
| Formula | C27H40O3 |
| Mol. mass | 412.605 g/mol |
| SMILES | eMolecules & PubChem |
|
|
 (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 or Daivonex.
Contents |
[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 for the vitamin D receptor (VDR), while being less than 1% as active as the calcitriol in regulating calcium metabolism. The vitamin D receptor 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 hypercalcaemia are rare.[4]
It is also available in combination with the synthetic glucocorticoid betamethasone as betamethasone/calcipotriol.
[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. McGraw-Hill, 2006. p. 1664. p. 1704-5.
- ^ Hardman et al. Hypercalcaemia 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
|
||||||||||||||||||||||||||||||||
|
|||||||||||||||||||||||||||||||||||
