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{{short description|Chemical compound}}
{{Drugbox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| IUPAC_name = (1-bromo-2,2-diphenylethenyl)benzene
| image = Triphenylbromoethylene.png
| width = 200px


| tradename = Bromylene, Eitriphin, Oestronyl, Prostilban, Tribenorm
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category =
| legal_AU = 
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =
| class = [[Nonsteroidal estrogen]]


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


| CAS_number_Ref =
| CAS_number = 1607-57-4
| CAS_supplemental =
| ATC_prefix =
| ATC_suffix =
| ATC_supplemental =
| PubChem = 15354
| IUPHAR_ligand =
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 14615
| UNII = MRW5MKO6LZ
| KEGG =
| ChEBI =
| ChEMBL =
| synonyms = TPBE; Tribromophenylethylene; Bromotriphenylethylene; Phenylstilbene bromide; Fenbrostilbenum


| C=20 | H=15 | Br=1
| SMILES = C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Br)C3=CC=CC=C3
| StdInChI_Ref =
| StdInChI = 1S/C20H15Br/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 = VUQVJIUBUPPCDB-UHFFFAOYSA-N
}}

'''Triphenylbromoethylene''' ('''TPBE'''; brand names '''Bromylene''', '''Eitriphin''', '''Oestronyl''', '''Prostilban''', '''Tribenorm'''), also known as '''bromotriphenylethylene''' or as '''phenylstilbene bromide''', is a [[synthetic compound|synthetic]] [[nonsteroidal estrogen]] of the [[triphenylethylene]] group that was marketed in the 1940s similarly to the closely related estrogen [[triphenylchloroethylene]].<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|page=1861|quote=C20H15Br. 1607-57-4. Bromotriphenylethene = Triphenylbromoethylene = Phenylstilbene bromide = 1,1',1"-(1-Bromo-1-ethenyl-2-yli- dene)tris[benzene] (•) S Bromylene, Fenbrostilbenum, Oestronyl, Phenylstilbene bromide, Prostilban, Tribenorm U Synthetic estrogen}}</ref><ref name="PatersonGilbert1949">{{cite journal | vauthors = Paterson E, Gilbert CW | title = Metabolism of the oestrogen triphenylbromoethylene | journal = Nature | volume = 163 | issue = 4151 | pages = 801–802 | date = May 1949 | pmid = 18128458 | doi = 10.1038/163801a0 | bibcode = 1949Natur.163..801P | s2cid = 13052481 }}</ref>

A di[[ethoxy]]lated [[chemical derivative|derivative]] of triphenylbromoethylene, [[estrobin]] (DBE), is also an [[estrogen (medication)|estrogen]], but, in contrast, was never marketed.<ref name="Emmens2013">{{cite book | vauthors = Emmens CW |title=Hormone Assay|url=https://books.google.com/books?id=cCzgBAAAQBAJ&pg=PA394|date=22 October 2013|publisher=Elsevier Science|isbn=978-1-4832-7286-3|pages=394–}}</ref> An [[ethyl group|ethyl]]ated derivative of triphenylbromoethylene, [[broparestrol]] (BDPE), is a [[selective estrogen receptor modulator]] (SERM) that has been marketed.<ref name="Elks2014">{{cite book | vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA183|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=183–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA139|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=139–}}</ref>

== See also ==
* [[Chlorotrianisene]]
* [[M2613]]
* [[Triphenyliodoethylene]]

== References ==
{{Reflist}}

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

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

{{genito-urinary-drug-stub}}

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