Tacalcitol

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

Tacalcitol
Clinical data
Other names(1α,24R)-1,24-Dihydroxyvitamin D3
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Topical
ATC code
Identifiers
IUPAC name
  • (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 InfoCard100.220.855
Chemical and physical data
FormulaC27H44O3
Molar mass416.64 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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 N
  • Key:BJYLYJCXYAMOFT-RSFVBTMBSA-N N
 NY (what is this?)  (verify)

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. Peters DC, Balfour JA (August 1997). "Tacalcitol". Drugs. 54 (2): 265–71, discussion 272. doi:10.2165/00003495-199754020-00005. PMID 9257082.
  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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