Chlorotrianiseneのソースを表示

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 460033186
| IUPAC_name = 1,1',1<nowiki>''</nowiki>-(2-chloroethene-1,1,2-triyl)tris(4-methoxybenzene); 11-chloro-4,13-dimethoxy-12-(''p''-methoxyphenyl)stilbene
| image = Chlorotrianisene.svg
| width = 225px

<!--Clinical data-->
| tradename = Tace, Estregur, Anisene, Clorotrisin, Merbentyl, Triagen, others
| Drugs.com = {{drugs.com|MTM|chlorotrianisene}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = X
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->
| legal_status =
| routes_of_administration = [[Oral administration|By mouth]]<ref name="Martindale" /><ref name="Meikle2003" />
| class = [[Nonsteroidal estrogen]]

<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism = Mono-''O''-[[demethylation]] ([[liver]] [[CYP450]])<ref name="pmid7295335">{{Cite journal |vauthors=Ruenitz PC, Toledo MM |date=August 1981 |title=Chemical and biochemical characteristics of O-demethylation of chlorotrianisene in the rat |journal=Biochem. Pharmacol. |volume=30 |issue=16 |pages=2203–7 |doi=10.1016/0006-2952(81)90088-5 |pmid=7295335}}</ref><ref name="Jordan1986">{{Cite book |url=https://books.google.com/books?id=7WmLZfGXST0C&pg=PA212 |title=Estrogen/antiestrogen Action and Breast Cancer Therapy |vauthors=Jordan VC |publisher=Univ of Wisconsin Press |year=1986 |isbn=978-0-299-10480-1 |page=212}}</ref>
| metabolites = [[Desmethylchlorotrianisene]]<ref name="pmid7295335" /><ref name="Jordan1986" />
| elimination_half-life =
| excretion =

<!--Identifiers-->
| IUPHAR_ligand = 7146
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 569-57-3
| ATC_prefix = G03
| ATC_suffix = CA06
| ATC_supplemental =
| PubChem = 11289
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00269
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10815
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6V5034L121
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00269
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 3641
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1200761
| synonyms = CTA; Trianisylchloroethylene; tri-''p''-Anisylchloroethylene; TACE; tris(''p''-Methoxyphenyl)-chloroethylene; NSC-10108

<!--Chemical data-->
| C=23 | H=21 | Cl=1 | O=3
| SMILES = COc1ccc(C(Cl)=C(c2ccc(OC)cc2)c2ccc(OC)cc2)cc1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C23H21ClO3/c1-25-19-10-4-16(5-11-19)22(17-6-12-20(26-2)13-7-17)23(24)18-8-14-21(27-3)15-9-18/h4-15H,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BFPSDSIWYFKGBC-UHFFFAOYSA-N
}}
<!-- Definition and medical uses -->
'''Chlorotrianisene''' ('''CTA'''), also known as '''tri-''p''-anisylchloroethylene''' ('''TACE''') and sold under the brand name '''Tace''' among others, is a [[nonsteroidal estrogen]] related to [[diethylstilbestrol]] (DES) which was previously used in the treatment of [[menopausal symptoms]] and [[estrogen deficiency]] in women and [[prostate cancer]] in men, among other indications, but has since been discontinued and is now no longer available.<ref name="Elks2014">{{Cite book |url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA263 |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies |vauthors=Elks J |date=14 November 2014 |publisher=Springer |isbn=978-1-4757-2085-3 |pages=263–}}</ref><ref name="IndexNominum2000">{{Cite book |url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA219 |title=Index Nominum 2000: International Drug Directory |date=January 2000 |publisher=Taylor & Francis |isbn=978-3-88763-075-1 |pages=219–}}</ref><ref name="MortonHall2012">{{Cite book |url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA73 |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms |vauthors=Morton IK, Hall JM |date=6 December 2012 |publisher=Springer Science & Business Media |isbn=978-94-011-4439-1 |pages=73–}}</ref><ref name="Martindale">{{Cite book |url=https://www.medicinescomplete.com/mc/martindale/2009/9029-q.htm |title=Martindale: The Complete Drug Reference |publisher=Pharmaceutical Press |year=2009 |isbn=978-0-85369-840-1 |veditors=Sweetman SC |edition=36th |location=London |page=2085 |chapter=Sex hormones and their modulators}}</ref><ref name="pmid7500443">{{Cite journal |vauthors=Cox RL, Crawford ED |date=December 1995 |title=Estrogens in the treatment of prostate cancer |journal=The Journal of Urology |volume=154 |issue=6 |pages=1991–8 |doi=10.1016/S0022-5347(01)66670-9 |pmid=7500443}}</ref> It is taken [[oral administration|by mouth]].<ref name="Martindale" /><ref name="Meikle2003" />

<!-- Side effects and mechanism -->
CTA is an [[estrogen (medication)|estrogen]], or an [[agonist]] of the [[estrogen receptor]]s, the [[biological target]] of estrogens like [[estradiol]].<ref name="MortonHall2012" /><ref name="Martindale" /><ref name="LuniwalJetson2012">{{Cite book |title=Analogue-Based Drug Discovery III |vauthors=Luniwal A, Jetson R, Erhardt P |year=2012 |isbn=9783527651085 |veditors=Fischer J, Ganellin CR, Rotella DP |pages=165–185 |chapter=Selective Estrogen Receptor Modulators |doi=10.1002/9783527651085.ch7}}</ref><ref name="pmid6541293">{{Cite journal |vauthors=Jordan VC, Lieberman ME |date=September 1984 |title=Estrogen-stimulated prolactin synthesis in vitro. Classification of agonist, partial agonist, and antagonist actions based on structure |journal=Molecular Pharmacology |volume=26 |issue=2 |pages=279–85 |pmid=6541293}}</ref> It is a high-[[intrinsic activity|efficacy]] [[partial agonist|partial]] estrogen and shows some properties of a [[selective estrogen receptor modulator]], with predominantly [[estrogen (medication)|estrogen]]ic activity but also some [[antiestrogen]]ic activity.<ref name="FischerGanellin2012" /><ref name="Sneader2005" /> CTA itself is inactive and is a [[prodrug]] in the body.<ref name="Meikle2003" /><ref name="Hadden2013" />

<!-- History, society, and culture -->
CTA was introduced for medical use in 1952.<ref name="Publishing2013" /> It has been marketed in the [[United States]] and [[Europe]].<ref name="Publishing2013" /><ref name="IndexNominum2000" /> However, it has since been discontinued and is no longer available in any country.<ref name="Martindale" /><ref name="Micromedex" />