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Calcipotriol

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(Redirected from Calcipotriene)

Calcipotriol
Clinical data
Trade namesDaivonex, others
Other namesCalcipotriene, MC 903, calcipotriene (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa608018
License data
Pregnancy
category
  • AU: B3
Routes of
administration		topical
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability5 to 6%
MetabolismLiver
ExcretionBiliary
Identifiers
  • (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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.119.473 Edit this at Wikidata
Chemical and physical data
FormulaC27H40O3
Molar mass412.614 g·mol−1
3D model (JSmol)
  • O[C@@H]1CC(\C(=C)[C@@H](O)C1)=C\C=C2/CCC[C@]4([C@H]2CC[C@@H]4[C@@H](/C=C/[C@@H](O)C3CC3)C)C
  • 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-/t17-,22-,23-,24+,25-,26+,27-/m1/s1 checkY
  • Key:LWQQLNNNIPYSNX-UROSTWAQSA-N checkY
 X markNcheckY (what is this?)  (verify)

Calcipotriol, also known as calcipotriene and sold under the brand name Dovonex among others, is a synthetic derivative of calcitriol, an active form of vitamin D. It is used topically in the treatment of psoriasis.[1]

It was patented in 1985 and approved for medical use in 1991.[2] It is on the World Health Organization's List of Essential Medicines.[3]

Calcipotriol is also available with the synthetic corticosteroid betamethasone dipropionate as the fixed-dose combination medication calcipotriol/betamethasone dipropionate for the treatment of plaque psoriasis.[4]

Medical uses

[edit]

Chronic plaque psoriasis is the chief medical use of calcipotriol.[5] It has also been used successfully in the treatment of alopecia areata.[6]

Contraindications

[edit]

Hypersensitivity, use on face, hypercalcaemia, or evidence of vitamin D toxicity are the only contraindications for calcipotriol use.[7]

Cautions include exposure to excessive natural or artificial light, due to the potential for calcipotriol to cause photosensitivity.[7]

Adverse effects

[edit]

Adverse effects by frequency:[5][7][8][9]

Very common (> 10% frequency)
  • Burning
  • Itchiness
  • Skin irritation
Common (1–10% frequency)
Uncommon (0.1–1% frequency)
Rare (< 0.1% frequency)

Interactions

[edit]

No drug interactions are known.[7]

Pharmacology

[edit]

Mechanism of action

[edit]

The efficacy of vitamin D receptor modulators (VDRMs) in the treatment of psoriasis was first noticed by the observation of patients receiving various forms of vitamin D in an osteoporosis study. Unexpectedly, some patients who also had psoriasis experienced dramatic reductions in lesion counts.[10] Calcipotriol has been shown to have comparable affinity with calcitriol for the vitamin D receptor (VDR) in vitro, while being less than 1% as active as the calcitriol in regulating calcium metabolism (when given orally to rats), making for an attactive drug candidate.[11] Human trials then demonstarated its safety and effectiveness as a topical medication.[12]

The precise mechanism of VDRMs such as calcipotriol in remitting psoriasis is not well understood. VDR is found inside the cells of many different tissues including the thyroid, bone, kidney, and T cells of the immune system. It is a nuclear receptor that directly binds to DNA and enables the transcription of genes. It has long been known that activating the vitamin D receptor (VDR) leads to decreased cell differentiation and proliferation in general, in lymphocytes specifically a suppression of activity. T cells are known to play a role in psoriasis, and it is thought that the VDR activation helps calm the overactive T cells.[13]

VDRMs also have a direct effect on the skin cells. In mouse studies, topical administration of calcipotriol and various other VDRMs to the ear and dorsal skin led to a dose-dependent increase in the production of the epithelial cell-derived cytokine TSLP by keratinocytes, and triggered atopic dermatitis at high concentrations. This process is also believed to be dependent the transcriptional activities of VDR.[14] As psoriasis is typically thought to be partially driven by Th1/Th17 inflammatory cytokines,[15] calcipotriol treatment at appropriate concentrations may alleviate psoriasis symptoms by repressing Th1/Th17 inflammation through TSLP production, which is linked to a Th2 response. This has not yet been confirmed.

Pharmacokinetics

[edit]

A small amount of topically applied calcipotriol is absorbed through the skin into the blood. This causes a very small but detectable effect on calcium homeostasis.[16] (At the time of its approval, topical calcipotriol was thought to have no effect on calcium metabolism based on the then-available clinical data.[13] This small systemic effect was discovered only after it was approved using improved measurement techniques.)

When absorbed into blood, calcipotriol undergoes rapid hepatic metabolism. Calcipotriol is metabolized to MC1046 (the α,β−unsaturated ketone analog), which is subsequently metabolized to its primary metabolite, the saturated ketone analog MC1080. MC1080 is then slowly metabolized to calcitroic acid.[17]

Society and culture

[edit]

Brand names

[edit]

It is sold under the brand name Dovonex in the United States, Daivonex outside North America, and Psorcutan in Germany.[citation needed]

References

[edit]
  1. ↑ Prendergast B, Harrison J, Kulkarni K, Baguneid M (27 October 2016). Oxford Handbook of Key Clinical Evidence. Oxford University Press. p. 101. ISBN 978-0-19-872942-6.
  2. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 452. ISBN 978-3-527-60749-5.
  3. ↑ The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. 2023. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  4. ↑ "Taclonex- calcipotriene and betamethasone dipropionate ointment". DailyMed. 21 May 2020. Retrieved 19 October 2020.
  5. 1 2 Rossi S, ed. (2013). Australian Medicines Handbook (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. ISBN 978-0-9805790-9-3.
  6. ↑ Kim DH, Lee JW, Kim IS, Choi SY, Lim YY, Kim HM, et al. (August 2012). "Successful treatment of alopecia areata with topical calcipotriol". Annals of Dermatology. 24 (3): 341–344. doi:10.5021/ad.2012.24.3.341. PMC 3412244. PMID 22879719.
  7. 1 2 3 4 "Dovonex, Calcitrene Ointment (calcipotriene) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. 15 October 2025. Retrieved 26 January 2014.
  8. ↑ "CALCIPOTRIENE (calcipotriene) solution [E. FOUGERA & CO. A division of Fougera Pharmaceuticals Inc.]". DailyMed. E. FOUGERA & CO. A division of Fougera Pharmaceuticals Inc. May 2012. Retrieved 26 January 2014.
  9. ↑ "PRODUCT INFORMATION DAIVONEX® CREAM Calcipotriol 50 microgram/g" (PDF). TGA eBusiness Services. LEO Pharma Pty Ltd. 28 April 2011. Retrieved 26 January 2014.
  10. ↑ Morimoto S, Kumahara Y (March 1985). "A patient with psoriasis cured by 1 alpha-hydroxyvitamin D3". Medical Journal of Osaka University. 35 (3–4): 51–54. PMID 4069059.
  11. ↑ Binderup L, Bramm E (March 1988). "Effects of a novel vitamin D analogue MC903 on cell proliferation and differentiation in vitro and on calcium metabolism in vivo". Biochemical Pharmacology. 37 (5): 889–895. doi:10.1016/0006-2952(88)90177-3. PMID 2830885.
  12. ↑ Kragballe K (December 1989). "Treatment of psoriasis by the topical application of the novel cholecalciferol analogue calcipotriol (MC 903)". Archives of Dermatology. 125 (12): 1647–1652. PMID 2531570.
  13. 1 2 Kragballe K, Iversen L (January 1993). "Calcipotriol. A new topical antipsoriatic". Dermatologic Clinics. 11 (1): 137–141. PMID 8435908.
  14. ↑ Li M, Hener P, Zhang Z, Kato S, Metzger D, Chambon P (August 2006). "Topical vitamin D3 and low-calcemic analogs induce thymic stromal lymphopoietin in mouse keratinocytes and trigger an atopic dermatitis". Proceedings of the National Academy of Sciences of the United States of America. 103 (31) (published 1 August 2006): 11736–11741. Bibcode:2006PNAS..10311736L. doi:10.1073/pnas.0604575103. PMC 1544239. PMID 16880407 – via Atypon Journals.
  15. ↑ Wong T, Hsu L, Liao W (1 February 2013). "Phototherapy in psoriasis: a review of mechanisms of action". Journal of Cutaneous Medicine and Surgery. 17 (1): 6–12. doi:10.2310/7750.2012.11124. PMC 3736829. PMID 23364144.
  16. ↑ Bourke JF, Mumford R, Whittaker P, Iqbal SJ, Le Van LW, Trevellyan A, et al. (December 1997). "The effects of topical calcipotriol on systemic calcium homeostasis in patients with chronic plaque psoriasis". Journal of the American Academy of Dermatology. 37 (6): 929–934. doi:10.1016/s0190-9622(97)70067-7. PMID 9418759.
  17. ↑ "Enstilar- calcipotriene and betamethasone dipropionate aerosol, foam". DailyMed. 18 October 2021. Retrieved 10 May 2025.
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