Tacalcitol

Last updated
Tacalcitol
Tacalcitol.svg
Clinical data
Other names(1α,24R)-1,24-Dihydroxyvitamin D3
AHFS/Drugs.com International Drug Names
Routes of
administration 		Topical
ATC code
Identifiers
  • (1S,3R,5Z,7E,24R)-9,10-secocholesta-5,7,10-triene-1,3,24-triol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.220.855 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C27H44O3
Molar mass 416.646 g·mol−1
3D model (JSmol)
  • O[C@@H]1CC(\C(=C)[C@@H](O)C1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CC[C@@H](O)C(C)C)C
  • InChI=1S/C27H44O3/c1-17(2)25(29)13-8-18(3)23-11-12-24-20(7-6-14-27(23,24)5)9-10-21-15-22(28)16-26(30)19(21)4/h9-10,17-18,22-26,28-30H,4,6-8,11-16H2,1-3,5H3/b20-9+,21-10-/t18-,22-,23-,24+,25-,26+,27-/m1/s1 X mark.svgN
  • Key:BJYLYJCXYAMOFT-RSFVBTMBSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Tacalcitol (1,24-dihydroxyvitamin D3) is a synthetic vitamin D3 analog. [1] Tacalcitol is marketed under several names, including Curatoderm and Bonalfa.

Contents

It is on the World Health Organization's List of Essential Medicines. [2]

Mechanism

Tacalcitol reduces excessive cell turnover in the epidermis by interacting with vitamin D receptors on keratinocytes. [3] [4]

Uses

It is usually prescribed by a general practitioner or dermatologist for the treatment of psoriasis, chronic chapped lips and other severe dry skin conditions because of its ability to reduce excessive skin cell turnover. [1] It is available as an ointment or lotion.

It has also been used for vitiligo [5] [6] and Hailey-Hailey disease. [7]

References

  1. 1 2 Peters DC, Balfour JA (August 1997). "Tacalcitol". Drugs. 54 (2): 265–71, discussion 272. doi:10.2165/00003495-199754020-00005. PMID   9257082. S2CID   263503145.
  2. ↑ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl: 10665/345533 . WHO/MHP/HPS/EML/2021.02.
  3. ↑ Matsumoto K, Hashimoto K, Kiyoki M, Yamamoto M, Yoshikawa K (February 1990). "Effect of 1,24R-dihydroxyvitamin D3 on the growth of human keratinocytes". The Journal of Dermatology. 17 (2): 97–103. doi:10.1111/j.1346-8138.1990.tb03714.x. PMID   2158504. S2CID   38248260.
  4. ↑ Fukuoka M, Sakurai K, Ohta T, Kiyoki M, Katayama I (2001). "Tacalcitol, an active vitamin D3, induces nerve growth factor production in human epidermal keratinocytes" . Skin Pharmacol. Appl. Skin Physiol. 14 (4): 226–33. doi:10.1159/000056351. PMID   11464105. S2CID   24302198.
  5. ↑ Leone G, Pacifico A, Iacovelli P, Paro Vidolin A, Picardo M (March 2006). "Tacalcitol and narrow-band phototherapy in patients with vitiligo". Clin. Exp. Dermatol. 31 (2): 200–5. doi:10.1111/j.1365-2230.2005.02037.x. PMID   16487090. S2CID   39021489.
  6. ↑ Birlea SA, Costin GE, Norris DA (April 2008). "Cellular and molecular mechanisms involved in the action of vitamin D analogs targeting vitiligo depigmentation". Current Drug Targets. 9 (4): 345–59. doi:10.2174/138945008783954970. PMID   18393827.
  7. ↑ Aoki T, Hashimoto H, Koseki S, Hozumi Y, Kondo S (November 1998). "1alpha,24-dihydroxyvitamin D3 (tacalcitol) is effective against Hailey-Hailey disease both in vivo and in vitro". Br. J. Dermatol. 139 (5): 897–901. doi:10.1046/j.1365-2133.1998.02522.x. PMID   9892963. S2CID   72418207.
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