Tacalcitol

Tacalcitol

Systematic (IUPAC) name
(1S,3R,5Z,7E,24R)-9,10-secocholesta-5,7,10-triene-1,3,24-triol
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Topical
Identifiers
CAS Number	57333-96-7
ATC code	D05AX04 (WHO)
PubChem	CID 5283734
IUPHAR/BPS	2780
ChemSpider	4446823
UNII	C2W72OJ5ZU
ChEMBL	CHEMBL340361
Synonyms	(1α,24R)-1,24-Dihydroxyvitamin D3
Chemical data
Formula	C27H44O3
Molar mass	416.64
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 Key:BJYLYJCXYAMOFT-RSFVBTMBSA-N
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Tacalcitol (1,24-dihydroxyvitamin D₃) is a synthetic vitamin D₃ analog.^[1]

Tacalcitol is marketed under several names, including Curatoderm and Bonalfa.

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^[2] and Hailey-Hailey disease.^[3]

References

1. 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.
2. 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.
3. 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.