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{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| IUPAC_name = 1,1',1<nowiki>''</nowiki>-(Ethene-1,1,2-triyl)tribenzene
| image = Triphenylethylene.svg
| width =


| tradename =
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category =
| legal_AU = 
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =


| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =


| CAS_number_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = S4ZLZ1K74B
| CAS_number = 58-72-0
| CAS_supplemental =
| ATC_prefix =
| ATC_suffix =
| PubChem = 6025
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 5803


| C=20 | H=16
| smiles = C1=CC=C(C=C1)C=C(C2=CC=CC=C2)C3=CC=CC=C3
| StdInChI = 1S/C20H16/c1-4-10-17(11-5-1)16-20(18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-16H
| StdInChIKey = MKYQPGPNVYRMHI-UHFFFAOYSA-N
| synonyms =
}}

'''Triphenylethylene''' ('''TPE''') is a simple [[aromatic hydrocarbon]] that possesses weak [[estrogen]]ic activity.<ref name="CRAIGFurr2010">{{cite book| vauthors = Dragan YP, Pitot HC | chapter = The Effect of Triphenylethylene Antiestrogens on Parameters of Multisage Hepatocarcinogenesis in the Rat | veditors = Jordan VD, Furr BJ |title=Hormone Therapy in Breast and Prostate Cancer| chapter-url = https://books.google.com/books?id=dM0uvBnxiN0C&pg=PA95 |date=5 February 2010|publisher=Springer Science & Business Media|isbn=978-1-59259-152-7|pages=95–}}</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> Its estrogenic effects 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> TPE was derived from structural modification of the more potent estrogen [[diethylstilbestrol]], which is a member of the [[stilbestrol]] group of [[nonsteroidal]] estrogens.<ref name="AvendanoMenendez2015">{{cite book| vauthors = Avendano C, Menendez JC | chapter = Anticancer Drugs that Modulate Hormone Action |title=Medicinal Chemistry of Anticancer Drugs| chapter-url = https://books.google.com/books?id=VEibBwAAQBAJ&pg=PA87 |date=11 June 2015|publisher=Elsevier Science|isbn=978-0-444-62667-7|pages= 81-131 (87) | doi = 10.1016/B978-0-444-62649-3.00003-X }}</ref>

TPE is the [[parent compound]] of a group of nonsteroidal [[estrogen receptor]] [[ligand (biochemistry)|ligand]]s.<ref name="CRAIGFurr2010" /><ref name="MaximovMcDaniel2013" /><ref name="CanoAlsina2006">{{cite book| vauthors = Marin F, Barbancho MC | chapter = Clinical Pharmacology of Selective Estrogen Receptor Modulators (SERMs)| veditors = Cano A, Calaf i Alsina J, Duenas-Diez JL |title=Selective Estrogen Receptor Modulators: A New Brand of Multitarget Drugs| chapter-url = https://books.google.com/books?id=heJDAAAAQBAJ&pg=PA52|date=22 September 2006|publisher=Springer Science & Business Media|isbn=978-3-540-34742-2|pages=52–}}</ref> It includes the [[estrogen]]s [[chlorotrianisene]], [[desmethylchlorotrianisene]], [[estrobin]] (DBE), [[M2613]], [[triphenylbromoethylene]], [[triphenylchloroethylene]], [[triphenyliodoethylene]], [[triphenylmethylethylene]]; the [[selective estrogen receptor modulator]]s (SERMs) [[afimoxifene]], [[brilanestrant]], [[broparestrol]], [[clomifene]], [[clomifenoxide]], [[droloxifene]], [[endoxifen]], [[etacstil]], [[fispemifene]], [[idoxifene]], [[miproxifene]], [[miproxifene phosphate]], [[nafoxidine]], [[ospemifene]], [[panomifene]], and [[toremifene]]. The [[antiestrogen]] [[ethamoxytriphetol]] (MER-25) is also closely related, but is technically not a derivative of TPE and is instead a [[triphenylethanol]] derivative. The tamoxifen [[metabolite]] and [[aromatase inhibitor]] [[norendoxifen]] is also a TPE derivative. In addition to their estrogenic activity, various TPE derivatives like tamoxifen and clomifene have been found to act as [[Protein kinase C#Inhibitors|protein kinase C inhibitor]]s.<ref name="pmid3458960">{{cite journal | vauthors = O'Brian CA, Liskamp RM, Solomon DH, Weinstein IB | title = Triphenylethylenes: a new class of protein kinase C inhibitors | journal = Journal of the National Cancer Institute | volume = 76 | issue = 6 | pages = 1243–1246 | date = June 1986 | pmid = 3458960 | doi = 10.1093/jnci/76.6.1243 }}</ref>

The [[affinity (pharmacology)|affinity]] of triphenylethylene for the rat [[estrogen receptor]] is about 0.002% relative to [[estradiol (medication)|estradiol]].<ref name="pmid10746941">{{cite journal | vauthors = Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, Tong W, Shi L, Perkins R, Sheehan DM | display-authors = 6 | title = The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands | journal = Toxicological Sciences | volume = 54 | issue = 1 | pages = 138–153 | date = March 2000 | pmid = 10746941 | doi = 10.1093/toxsci/54.1.138 | doi-access = free }}</ref><ref name="pmid11258977">{{cite journal | vauthors = Fang H, Tong W, Shi LM, Blair R, Perkins R, Branham W, Hass BS, Xie Q, Dial SL, Moland CL, Sheehan DM | display-authors = 6 | title = Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens | journal = Chemical Research in Toxicology | volume = 14 | issue = 3 | pages = 280–294 | date = March 2001 | pmid = 11258977 | doi = 10.1021/tx000208y }}</ref> For comparison, the relative binding affinities of derivatives of triphenylethylene were 1.6% for [[tamoxifen]], 175% for [[afimoxifene]] (4-hydroxytamoxifen), 15% for [[droloxifene]], 1.4% for [[toremifene]] (4-chlorotamoxifen), 0.72% for [[clomifene]], and 0.72% for [[nafoxidine]].<ref name="WittliffKerr2005">{{cite book | vauthors = Wittliff JL, Kerr II DA, Andres SA | year = 2005 | chapter = Estrogens IV: Estrogen-Like Pharmaceuticals | veditors = Wexler P | title = Encyclopedia of Toxicology | edition = 2nd | volume = Dib-L | pages = 254–258 |publisher=Elsevier | isbn = 978-0-08-054800-5 | chapter-url = https://books.google.com/books?id=dEnbcGW44RYC&pg=PT3318 | doi = 10.1016/B0-12-369400-0/01087-5 }}</ref><ref name="pmid10746941" /><ref name="pmid11258977" />

== See also ==
* [[List of SERMs]]
* [[Benzothiophene]] – parent compound for another group of nonsteroidal SERMs that includes [[raloxifene]]
* [[Phenanthrene]] – parent compound of [[steroid]]al estrogens like [[estradiol]]
* [[Chrysene]] – parent compound of a group of nonsteroidal weak estrogens that includes [[2,8-dihydroxyhexahydrochrysene|2,8-DHHHC]] and [[tetrahydrochrysene]]
* [[Doisynolic acid]] – parent compound of a group of nonsteroidal estrogens that includes [[doisynoestrol]]
* [[Allenolic acid]] – parent compound of a group of nonsteroidal estrogens that includes [[methallenestril]]

== References ==
{{Reflist}}

{{Estrogen receptor modulators}}

[[Category:Selective estrogen receptor modulators]]
[[Category:Synthetic estrogens]]
[[Category:Triphenylethylenes| ]]

{{pharmacology-stub}}

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