View source for Chemistry:Triphenylchloroethylene

{{short description|Synthetic form of estrogen}}
{{Drugbox
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| IUPAC_name = (1-chloro-2,2-diphenylethenyl)benzene
| image = Triphenylchloroethylene.png
| width = 200px

<!--Clinical data-->
| tradename = Gynosone, Oestrogyl
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| class = [[Biology:Nonsteroidal estrogen|Nonsteroidal estrogen]]

<!--Pharmacokinetic data-->
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<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 18084-97-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = AV6NM693EG
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| PubChem = 87450
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| ChemSpiderID = 78884
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| synonyms = TPCE; Triphenylchlorethylene; Chlorotriphenylethylene; Phenylstilbene chloride

<!--Chemical data-->
| C=20 | H=15 | Cl=1
| SMILES = C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Cl)C3=CC=CC=C3
| StdInChI_Ref = 
| StdInChI = 1S/C20H15Cl/c21-20(18-14-8-3-9-15-18)19(16-10-4-1-5-11-16)17-12-6-2-7-13-17/h1-15H
| StdInChIKey_Ref = 
| StdInChIKey = QEQFTTCZLHLKFX-UHFFFAOYSA-N
}}

'''Triphenylchloroethylene''' ('''TPCE'''; brand names '''Gynosone''', '''Oestrogyl'''), or '''triphenylchlorethylene''', also known as '''chlorotriphenylethylene''' or as '''phenylstilbene chloride''', is a synthetic [[Biology:Nonsteroidal estrogen|nonsteroidal estrogen]] of the [[Chemistry:Triphenylethylene|triphenylethylene]] group that was marketed in the 1940s for the treatment of menopausal [[Medicine:Symptom|symptom]]s, vaginal atrophy, lactation suppression, and all other [[Chemistry:Estrogen (medication)|estrogen]]-indicated conditions.<ref name="NegwerScharnow2001">{{cite book| vauthors = Negwer M, Scharnow HG |title=Organic-chemical drugs and their synonyms: (an international survey)|url=https://books.google.com/books?id=zmpqAAAAMAAJ|year=2001|publisher=Wiley-VCH|isbn=978-3-527-30247-5|pages=1861–1862|quote=C20H15Cl 18084-97-4 Chlorotriphenylethene = Triphenylchloroethylene = Phenylstilbene chloride = 1,1',1"-(1-Chloro-1-ethenyl-2-ylidene)tris[benzene] (•) S Gynosone, Oestrogyl, Phenylstilbene chloride U Synthetic estrogen}}</ref><ref name="pmid20259249">{{cite journal | vauthors = Emmens CW | title = Halogen-substituted oestrogens related to triphenylethylene | journal = The Journal of Endocrinology | volume = 5 | issue = 3 | pages = 170–173 | date = July 1947 | pmid = 20259249 | doi = 10.1677/joe.0.0050170 }}</ref><ref name="pmc2181944">{{cite journal | url = https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2181944/pdf/procrsmed00542-0002.pdf | journal = Proc R Soc Med|volume= 39|issue=11|date= Sep 1946 | title = "Gynosone" A New Synthetic Oestrogen | department = Advertisement | pmc=2181944}}</ref>

The [[Chemistry:Estrogen (medication)|estrogen]]ic effects of triphenylethylene, the parent compound of triphenylchloroethylene, were discovered in 1937.<ref name="Li2009">{{cite book| vauthors = Li JJ  | chapter = Genesis of Statins |title=Triumph of the Heart: The Story of Statins| chapter-url = https://books.google.com/books?id=-GPl1PA5EgMC&pg=PA33|date=3 April 2009|publisher=Oxford University Press, USA|isbn=978-0-19-532357-3|pages=33–}}</ref> Triphenylchloroethylene was first reported in 1938 and was found to have 20 to 100 times the estrogenic activity of the relatively weak triphenylethylene, a potentiation of effect that was afforded by its [[Chemistry:Halogen|halogen]] [[Chemistry:Substituent|substituent]].<ref name="pmid20259249" /><ref name="pmid21013428">{{cite journal | vauthors = Solmssen UV | title = Synthetic estrogens and the relation between their structure and their activity | journal = Chemical Reviews | volume = 37 | issue = 3 | pages = 481–598 | date = December 1945 | pmid = 21013428 | doi = 10.1021/cr60118a004 }}</ref> The drug has a relatively long duration of action when administered via [[Medicine:Subcutaneous injection|subcutaneous injection]] but a duration similar to that of [[Chemistry:Diethylstilbestrol|diethylstilbestrol]] or [[Chemistry:Estradiol benzoate|estradiol benzoate]] when administered [[Medicine:Oral administration|orally]].<ref name="pmid20259249" /><ref name="Jordan1986">{{cite book | vauthors = Jordon VC, Koch R, Lieberman ME | chapter = Structure-Activity Relationships of Nonsteroidal Estrogens and Antiestrogens | veditors = Jordan VC |title=Estrogen/antiestrogen Action and Breast Cancer Therapy| chapter-url = https://books.google.com/books?id=7WmLZfGXST0C&pg=PA23|year=1986|publisher=University of Wisconsin Press|isbn=978-0-299-10480-1|pages=23–}}</ref><ref name="MaximovMcDaniel2013">{{cite book| vauthors = Maximov PY, McDaniel RE, Jordan VC | chapter = Discovery and Pharmacology of Nonsteroidal Estrogens and Antiestrogens |title=Tamoxifen: Pioneering Medicine in Breast Cancer| chapter-url=https://books.google.com/books?id=p-W5BAAAQBAJ&pg=PA4|date=23 July 2013|publisher=Springer Science & Business Media|isbn=978-3-0348-0664-0|pages=4–}}</ref> Along with diethylstilbestrol and [[Chemistry:Triphenylmethylethylene|triphenylmethylethylene]], triphenylchloroethylene was studied in 1944 by Sir Alexander Haddow for the treatment of [[Medicine:Breast cancer|breast cancer]] and was found to be significantly effective, and this is historically notable in that it was the first time that high-dose estrogens were found to be effective in the treatment of breast cancer.<ref name="Jordan2013">{{cite book| vauthors = Lewis-Wambi J, Jordan VC | chapter = Diethylstilbestrol: A Tragedy in Reproductive Endocrinology But a Pioneering Cancer Treatment | veditors = Jordan VC |title=Estrogen Action, Selective Estrogen Receptor Modulators and Women's Health: Progress and Promise| chapter-url=https://books.google.com/books?id=ZM26CgAAQBAJ&pg=PA42|date=27 May 2013|publisher=World Scientific|isbn=978-1-84816-959-3|pages=42–}}</ref><ref name="Wagener2009">{{cite book| vauthors = Wagener DJ | chapter = The history of the hormonal treatment of cancer |title=The History of Oncology| chapter-url=https://books.google.com/books?id=53fmwacXu44C&pg=PA189|date=13 July 2009|publisher=Bohn Stafleu van Loghum|isbn=978-90-313-6143-4|pages=189–}}</ref>

[[Chemistry:Chlorotrianisene|Chlorotrianisene]], or tri-''p''-anisylchloroethylene (TACE), is a potent marketed estrogen and a [[Chemistry:Chemical derivative|derivative]] of triphenylchloroethylene in which each of the three phenyl rings has been substituted with a 4-[[Chemistry:Methoxy group|methoxy group]].<ref name="pmid21013428"/><ref name="Allahbadia2006">{{cite book| vauthors = Lisi F | chapter = Adjunctions to Clomiphene Citrate | veditors = Allahbadia G |title=Contemporary Perspectives on Assisted Reproductive Technology| chapter-url = https://books.google.com/books?id=Zx-lRwGFU4gC&pg=PA18|year=2006|publisher=Elsevier India|isbn=978-81-8147-782-8|pages=18–}}</ref> [[Chemistry:Estrobin|Estrobin]], or DBE, is a related, never-marketed estrogen in which there is a [[Chemistry:Bromine|bromine]] in place of the [[Chemistry:Chlorine|chlorine]] and two of the three phenyl rings have ethoxy groups.<ref name="pmid21013428" /> [[Chemistry:Broparestrol|Broparestrol]], or BDPE is a marketed [[Chemistry:Selective estrogen receptor modulator|selective estrogen receptor modulator]] (SERM) that has a bromine in place of the chlorine of triphenylchloroethylene and a 4-[[Chemistry:Ethyl group|ethyl group]] on one of the phenyl rings. The SERM [[Chemistry:Clomifene|clomifene]] is also a derivative of triphenylchloroethylene.<ref name="GardnerWeissman2012">{{cite book | vauthors = Shoham Z, Howles CM | chapter = Drugs used for ovarian stimulation: Clomiphene citrate, aromatase inhibitors, metformin, gonadotropins, gonadotropin-releasing hormone analogs and recombinant gonadotropins | veditors = Gardner DK, Weissman A, Howles CM, Shoham Z |title=Textbook of Assisted Reproductive Techniques Fourth Edition: Volume 2: Clinical Perspectives| chapter-url=https://books.google.com/books?id=Ap1_AwAAQBAJ&pg=PA51|date=27 June 2012|publisher=CRC Press|isbn=978-1-84184-972-0|pages=51–}}</ref>

== See also ==
* [[Chemistry:Triphenylbromoethylene|Triphenylbromoethylene]]
* [[Chemistry:Triphenyliodoethylene|Triphenyliodoethylene]]

== References ==
{{Reflist}}

{{Estrogens and antiestrogens}}
{{Estrogen receptor modulators}}

[[Category:Abandoned drugs]]
[[Category:Organochlorides]]
[[Category:Synthetic estrogens]]
[[Category:Triphenylethylenes]]


{{Sourceattribution|Triphenylchloroethylene}}