tacalcitol
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 376121485
| IUPAC_name = (1S,3R,5Z,7E,24R)-9,10-secocholesta-5,7,10-triene-1,3,24-triol
| image = Tacalcitol.svg
| image_class = skin-invert-image
| tradename =
| Drugs.com = {{drugs.com|international|tacalcitol}}
| pregnancy_AU =
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| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = Topical
| bioavailability =
| protein_bound =
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| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 57333-96-7
| ATC_prefix = D05
| ATC_suffix = AX04
| PubChem = 5283734
| IUPHAR_ligand = 2780
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = C2W72OJ5ZU
| ChEBI = 32176
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 340361
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4446823
| C=27 | H=44 | O=3
| synonyms = (1α,24R)-1,24-Dihydroxyvitamin D3
| 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
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = BJYLYJCXYAMOFT-RSFVBTMBSA-N
}}
Tacalcitol (1,24-dihydroxyvitamin D3) is a synthetic vitamin D3 analog.{{cite journal | vauthors = Peters DC, Balfour JA | title = Tacalcitol | journal = Drugs | volume = 54 | issue = 2 | pages = 265–71; discussion 272 | date = August 1997 | pmid = 9257082 | doi = 10.2165/00003495-199754020-00005 | s2cid = 263503145 }} Tacalcitol is marketed under several names, including Curatoderm and Bonalfa.
It is on the World Health Organization's List of Essential Medicines.{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}
Mechanism
Tacalcitol reduces excessive cell turnover in the epidermis by interacting with vitamin D receptors on keratinocytes.{{cite journal | vauthors = Matsumoto K, Hashimoto K, Kiyoki M, Yamamoto M, Yoshikawa K | title = Effect of 1,24R-dihydroxyvitamin D3 on the growth of human keratinocytes | journal = The Journal of Dermatology | volume = 17 | issue = 2 | pages = 97–103 | date = February 1990 | pmid = 2158504 | doi = 10.1111/j.1346-8138.1990.tb03714.x | s2cid = 38248260 }}{{cite journal |vauthors=Fukuoka M, Sakurai K, Ohta T, Kiyoki M, Katayama I |title=Tacalcitol, an active vitamin D3, induces nerve growth factor production in human epidermal keratinocytes |journal=Skin Pharmacol. Appl. Skin Physiol. |volume=14 |issue=4 |pages=226–33 |year=2001 |pmid=11464105 |doi= 10.1159/000056351|doi-broken-date=10 December 2024 |s2cid=24302198 |url=http://content.karger.com/produktedb/produkte.asp?typ=fulltext&file=sph14226}}
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{{cite journal |vauthors=Leone G, Pacifico A, Iacovelli P, Paro Vidolin A, Picardo M |title=Tacalcitol and narrow-band phototherapy in patients with vitiligo |journal=Clin. Exp. Dermatol. |volume=31 |issue=2 |pages=200–5 |date=March 2006 |pmid=16487090 |doi=10.1111/j.1365-2230.2005.02037.x |s2cid=39021489 }}{{cite journal | vauthors = Birlea SA, Costin GE, Norris DA | title = Cellular and molecular mechanisms involved in the action of vitamin D analogs targeting vitiligo depigmentation | journal = Current Drug Targets | volume = 9 | issue = 4 | pages = 345–59 | date = April 2008 | pmid = 18393827 | doi = 10.2174/138945008783954970 }} and Hailey-Hailey disease.{{cite journal |vauthors=Aoki T, Hashimoto H, Koseki S, Hozumi Y, Kondo S |title=1alpha,24-dihydroxyvitamin D3 (tacalcitol) is effective against Hailey-Hailey disease both in vivo and in vitro |journal=Br. J. Dermatol. |volume=139 |issue=5 |pages=897–901 |date=November 1998 |pmid=9892963 |doi= 10.1046/j.1365-2133.1998.02522.x|s2cid=72418207 }}
References
{{Reflist|2}}
{{Antipsoriatics}}
{{Vitamin D receptor modulators}}
{{Vitamins}}