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Tacalcitol

Clinical data
Other names	(1α,24R)-1,24-Dihydroxyvitamin D3
AHFS/Drugs.com	International Drug Names
Routes of administration	Topical
ATC code	D05AX04 (WHO)
Identifiers
IUPAC name (1S,3R,5Z,7E,24R)-9,10-secocholesta-5,7,10-triene-1,3,24-triol
CAS Number	57333-96-7
PubChem CID	5283734
IUPHAR/BPS	2780
ChemSpider	4446823
UNII	C2W72OJ5ZU
ChEBI	CHEBI:32176
ChEMBL	ChEMBL340361
CompTox Dashboard (EPA)	DTXSID90905111
ECHA InfoCard	100.220.855
Chemical and physical data
Formula	C27H44O3
Molar mass	416.646 g·mol
3D model (JSmol)	Interactive image
SMILES O1CC(\C(=C)(O)C1)=C\C=C2/CCC3(2CC3(C)CC(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 Key:BJYLYJCXYAMOFT-RSFVBTMBSA-N
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Tacalcitol (1,24-dihydroxyvitamin D₃) is a synthetic vitamin D₃ analog. Tacalcitol is marketed under several names, including Curatoderm and Bonalfa.

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

Mechanism

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

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. It is available as an ointment or lotion.

It has also been used for vitiligo and Hailey-Hailey disease.

References

1. ^ 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 (inactive 10 December 2024). PMID 11464105. S2CID 24302198.{{cite journal}}: CS1 maint: DOI inactive as of December 2024 (link)
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.

• Secosteroids
• Vitamin D