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Calcipotriol

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Title: Calcipotriol  
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Subject: Hypercalcaemia, Vitamin D, Ergocalciferol, Dihydrotachysterol, Cholecalciferol
Collection: Alcohols, Cyclopropanes, Indanes, Indenes, Secondary Alcohols, Secosteroids, Vitamin D
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Calcipotriol

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-methylidenecyclohyytyexane-1,3-diol
Clinical data
Trade names Daivobex, Dovobex, Sorilux
AHFS/Drugs.com
MedlinePlus
Pregnancy
category
  • AU: B3
  • US: C (Risk not ruled out)
Legal status
Routes of
administration
Topical
Pharmacokinetic data
Bioavailability 5 to 6%
Metabolism Hepatic
Excretion Biliary
Identifiers
CAS Registry Number  Y
ATC code D05
PubChem CID:
IUPHAR/BPS
DrugBank  Y
ChemSpider  Y
UNII  Y
KEGG  Y
ChEBI  Y
ChEMBL  N
Chemical data
Formula C27H40O3
Molecular mass 412.605 g/mol
 N   

Calcipotriol (INN) or calcipotriene (USAN) is a synthetic derivative of calcitriol, a form of vitamin D. It is used in the treatment of psoriasis, marketed under the trade name "Dovonex" in the United States, "Daivonex" outside of North America, and "Psorcutan" in Germany. This medication is safe for long-term application in psoriatic skin conditions.

Contents

  • Medical uses 1
  • Adverse effects 2
    • Contraindications 2.1
    • Interactions 2.2
  • Mechanism 3
  • References 4
  • External links 5

Medical uses

Chronic plaque psoriasis is the chief medical use of calcipotriol.[1] It has also been used successfully in the treatment of alopecia areata.[2]

Adverse effects

Adverse effects by frequency:[1][3][4][5]

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

Contraindications

Hypersensitivity, use on face, hypercalcaemia, or evidence of vitamin D toxicity are the only contraindications for calcipotriol use.[3]

Cautions include exposure to excessive natural or artificial light, due to the potential for calcipotriol to cause photosensitivity.[3]

Interactions

No drug interactions are known.[3]

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, some patients who also suffered from psoriasis experienced dramatic reductions in lesion counts.[6]

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.

References

  1. ^ a b Rossi, S, ed. (2013). Australian Medicines Handbook (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust.  
  2. ^ Kim, D. H.; Lee, J. W.; Kim, I. S.; Choi, S. Y.; Lim, Y. Y.; Kim, H. M.; Kim, B. J.; Kim, M. N. (2012). "Successful Treatment of Alopecia Areata with Topical Calcipotriol". Annals of Dermatology 24 (3): 341–344.  
  3. ^ a b c d "Dovonex, Calcitrene Ointment (calcipotriene) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 26 January 2014. 
  4. ^ "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. 
  5. ^ "PRODUCT INFORMATION DAIVONEX® CREAM Calcipotriol 50 microgram/g" (PDF). TGA eBusiness Services. LEO Pharma Pty Ltd. 28 April 2011. Retrieved 26 January 2014. 
  6. ^ Morimoto, S., Kumahara, Y. A patient with psoriasis cured by 1-α-hydroxyvitamin D3. Med. J. Osaka Univ., 1985, 35:51–54

External links

  • Calcipotriene information - U.S. NLM/NIH
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