Calcipotriol

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Calcipotriol
Calcipotriol.svg
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 monograph
MedlinePlus a608018
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 Number 112965-21-6 YesY
ATC code D05AX02 (WHO)
PubChem CID: 5288783
IUPHAR/BPS 2778
DrugBank DB02300 YesY
ChemSpider 4450880 YesY
UNII 143NQ3779B YesY
KEGG D01125 YesY
ChEBI CHEBI:50749 YesY
ChEMBL CHEMBL100918 N
Chemical data
Formula C27H40O3
Molecular mass 412.605 g/mol
  • 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 YesY
  • Key:LWQQLNNNIPYSNX-UROSTWAQSA-N YesY
 NYesY (what is this?)  (verify)

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.

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]

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]

Adverse effects

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

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

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Uncommon (0.1–1% frequency)
Rare (< 0.1% frequency)

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Interactions

No drug interactions are known.[3]

Pharmacology

Mechanism of action

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.

Pharmacokinetics

After application and systemic uptake, 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.[7]

The metabolites of calcipotriol are less potent than the parent compound.

Physical and chemical properties

Calcipotriol is a white to almost white crystalline compound.

References

  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 3.2 3.3 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Morimoto, S., Kumahara, Y. A patient with psoriasis cured by 1-α-hydroxyvitamin D3. Med. J. Osaka Univ., 1985, 35:51–54
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.

External links

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