Triphenylbromoethylene

Triphenylbromoethylene (TPBE; brand names Bromylene, Eitriphin, Oestronyl, Prostilban, Tribenorm), also known as bromotriphenylethylene or as phenylstilbene bromide, is a synthetic nonsteroidal estrogen of the triphenylethylene group that was marketed in the 1940s similarly to the closely related estrogen triphenylchloroethylene.[1][2]

Triphenylbromoethylene
Clinical data
Trade namesBromylene, Eitriphin, Oestronyl, Prostilban, Tribenorm
Other namesTPBE; Tribromophenylethylene; Bromotriphenylethylene; Phenylstilbene bromide; Fenbrostilbenum
Drug classNonsteroidal estrogen
Identifiers
IUPAC name
  • (1-bromo-2,2-diphenylethenyl)benzene
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.015.029
Chemical and physical data
FormulaC20H15Br
Molar mass335.244 g·mol−1
3D model (JSmol)
SMILES
  • C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Br)C3=CC=CC=C3
InChI
  • InChI=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
  • Key:VUQVJIUBUPPCDB-UHFFFAOYSA-N

A diethoxylated derivative of triphenylbromoethylene, estrobin (DBE), is also an estrogen, but, in contrast, was never marketed.[3] An ethylated derivative of triphenylbromoethylene, broparestrol (BDPE), is a selective estrogen receptor modulator (SERM) that has been marketed.[4][5]

See also

References
  1. Negwer M, Scharnow HG (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 1861. ISBN 978-3-527-30247-5. 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
  2. Paterson E, Gilbert CW (May 1949). "Metabolism of the oestrogen triphenylbromoethylene". Nature. 163 (4151): 801–802. Bibcode:1949Natur.163..801P. doi:10.1038/163801a0. PMID 18128458. S2CID 13052481.
  3. Emmens CW (22 October 2013). Hormone Assay. Elsevier Science. pp. 394–. ISBN 978-1-4832-7286-3.
  4. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 183–. ISBN 978-1-4757-2085-3.
  5. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 139–. ISBN 978-3-88763-075-1.
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