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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| IUPAC_name = (1''S'',3''R'',5''Z'',7''E'',24''R'')-9,10-secocholesta-5,7,10-triene-1,3,24-triol |
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| Watchedfields = changed |
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|synonyms = <small>(1''R'',3''S'',5''Z'')-5--7a-methyl-2,3,3a,5,6,7-hexahydro-1''H''-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol</small> |
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| verifiedrevid = 376121485 |
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| image = |
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| IUPAC_name = (1''S'',3''R'',5''Z'',7''E'',24''R'')-9,10-secocholesta-5,7,10-triene-1,3,24-triol |
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| CAS_number = 57333-96-7 |
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| image = Tacalcitol.svg |
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| ATC_prefix = D05 |
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| ATC_suffix = AX04 |
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<!--Clinical data--> |
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| PubChem = 5283734 |
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| DrugBank = |
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| tradename = |
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| Drugs.com = {{drugs.com|international|tacalcitol}} |
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| C=27 | H=44 | O=3 |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| molecular_weight = 416.64 |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| bioavailability = |
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| pregnancy_category = |
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| protein_bound = |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| metabolism = |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| elimination_half-life = |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = Topical |
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| routes_of_administration = Topical |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 57333-96-7 |
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| ATC_prefix = D05 |
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| ATC_suffix = AX04 |
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| PubChem = 5283734 |
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| IUPHAR_ligand = 2780 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = C2W72OJ5ZU |
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| ChEBI = 32176 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 340361 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4446823 |
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<!--Chemical data--> |
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| C=27 | H=44 | O=3 |
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| synonyms = (1α,24''R'')-1,24-Dihydroxyvitamin D<sub>3</sub> |
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| smiles = O1CC(\C(=C)(O)C1)=C\C=C2/CCC3(2CC3(C)CC(O)C(C)C)C |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = BJYLYJCXYAMOFT-RSFVBTMBSA-N |
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}} |
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}} |
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'''Tacalcitol''' is a synthetic vitamin D<sub>3</sub> analogue.<ref name="pmid11464105">{{cite journal |author=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= |url=http://content.karger.com/produktedb/produkte.asp?typ=fulltext&file=sph14226}}</ref> |
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'''Tacalcitol''' (1,24-dihydroxyvitamin D<sub>3</sub>) is a synthetic ] analog.<ref name="pmid9257082">{{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 }}</ref> Tacalcitol is marketed under several names, including '''Curatoderm''' and '''Bonalfa'''. |
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Tacalcitol is marketed under several names, including '''Curatoderm''' and '''Bonalfa'''. |
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It is on the ].<ref name="WHO22nd">{{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 }}</ref> |
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==Mechanism== |
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==Mechanism== |
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Tacalcitol reduces excessive cell turnover in the epidermis by interacting with ]s on ].<ref name="pmid2158504">{{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 }}</ref><ref name="pmid11464105">{{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}}</ref> |
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Tacalcitol exerts its biological activity by preventing the proliferation of keratinocytes. |
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==Uses== |
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==Uses== |
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It is usually prescribed by a general practitioner or dermatologist for the treatment of ], chronic ] and other severe dry skin conditions because of its ability to reduce excessive skin cell turnover.<ref name="pmid9257082" /> It is available as an ointment or lotion. |
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It is used to treat ]. |
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It has been used for ]<ref name="pmid16487090">{{cite journal |author=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 |year=2006 |month=March |pmid=16487090 |doi=10.1111/j.1365-2230.2005.02037.x |url=http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0307-6938&date=2006&volume=31&issue=2&spage=200}}</ref> and ].<ref name="pmid9892963">{{cite journal |author=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 |year=1998 |month=November |pmid=9892963 |doi= 10.1046/j.1365-2133.1998.02522.x|url=http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0007-0963&date=1998&volume=139&issue=5&spage=897}}</ref> |
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It has also been used for ]<ref name="pmid16487090">{{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 }}</ref><ref name="pmid18393827">{{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 }}</ref> and ].<ref name="pmid9892963">{{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 }}</ref> |
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== References == |
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== References == |
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{{reflist}} |
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{{Reflist|2}} |
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{{Antipsoriatics}} |
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{{Antipsoriatics}} |
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{{Vitamin D receptor modulators}} |
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] |
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] |
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] |
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{{Vitamins}} |
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{{dermatologic-drug-stub}} |
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] |
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