Tacalcitol

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−1
3D model (JSmol)	Interactive image;
	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.

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

^ ^a ^b Peters DC, Balfour JA (August 1997). "Tacalcitol". Drugs. 54 (2): 265–71, discussion 272. doi:10.2165/00003495-199754020-00005. PMID 9257082. S2CID 263503145.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

v t e Vitamin D receptor modulators
VDRTooltip Vitamin D receptor	Agonists: 7-Dehydrocholesterol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin D₃) Dihydrotachysterol Doxercalciferol EB-1089 Eldecalcitol Ercalcidiol Ercalcitriol Ergocalciferol (vitamin D₂) Lithocholic acid Maxacalcitol Paricalcitol Tacalcitol Antagonists: ZK159222 TEI-9647
See also Receptor/signaling modulators

Tacalcitol

Mechanism

Uses

References

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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^Y
PubChem CID	5283734
IUPHAR/BPS	2780
ChemSpider	4446823^N
UNII	C2W72OJ5ZU
ChEBI	CHEBI:32176
ChEMBL	ChEMBL340361^N
CompTox Dashboard (EPA)	DTXSID90905111
ECHA InfoCard	100.220.855
Chemical and physical data
Formula	C₂₇H₄₄O₃
Molar mass	416.646 g·mol⁻¹
3D model (JSmol)	Interactive image
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)