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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| IUPAC_name = (1''S'',3''R'',5''Z'',7''E'',24''R'')-9,10-secocholesta-5,7,10-triene-1,3,24-triol
| Watchedfields = changed
|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>
| verifiedrevid = 376121485
| image =
| IUPAC_name = (1''S'',3''R'',5''Z'',7''E'',24''R'')-9,10-secocholesta-5,7,10-triene-1,3,24-triol
| CAS_number = 57333-96-7
| image = Tacalcitol.svg
| ATC_prefix = D05

| ATC_suffix = AX04
<!--Clinical data-->
| PubChem = 5283734
| DrugBank = | tradename =
| Drugs.com = {{drugs.com|international|tacalcitol}}
| C=27 | H=44 | O=3
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| molecular_weight = 416.64
| pregnancy_US = <!-- A / B / C / D / X -->
| bioavailability =
| pregnancy_category =
| protein_bound =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| metabolism =
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| elimination_half-life =
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| excretion =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category=
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| routes_of_administration = Topical | routes_of_administration = Topical

<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =

<!--Identifiers-->
| 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

<!--Chemical data-->
| C=27 | H=44 | O=3
| synonyms = (1α,24''R'')-1,24-Dihydroxyvitamin D<sub>3</sub>
| smiles = O1CC(\C(=C)(O)C1)=C\C=C2/CCC3(2CC3(C)CC(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''' 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>


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

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>


==Mechanism== ==Mechanism==
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>
Tacalcitol exerts its biological activity by preventing the proliferation of keratinocytes.


==Uses== ==Uses==
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.
It is used to treat ].


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> 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>


== References == == References ==
{{reflist}} {{Reflist|2}}


{{Antipsoriatics}} {{Antipsoriatics}}
{{Vitamin D receptor modulators}}

] ]
] ]
{{Vitamins}}


{{dermatologic-drug-stub}}

]