Broparestrol

Broparestrol (INN) (brand names Acnestrol, Longestrol; former developmental code name LN-107), also known as α-bromo-α,β-diphenyl-β-p-ethylphenylethylene (BDPE), is a synthetic, nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group[1] that has been used in Europe as a dermatological agent and for the treatment of breast cancer.[2][3][4][5][6] The drug is described as slightly estrogenic[7] and potently antiestrogenic,[8][9] and inhibits mammary gland development and suppresses prolactin levels in animals.[10] It is structurally related to clomifene and diethylstilbestrol.[6][10] Broparestrol is a mixture of E- and Z- isomers (LN-1643 and LN-2299, respectively), both of which are active and are similarly antiestrogenic but, unlike broparestrol, were never marketed.[2]

Broparestrol
Clinical data
Trade namesAcnestrol, Longestrol
Other namesLN-107; α-Bromo-α,β-diphenyl-β-p-ethylphenylethylene; BDPE
Pregnancy
category
  • X (Contraindicated)
Routes of
administration		By mouth
Drug classSelective estrogen receptor modulator
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • 1-(2-bromo-1,2-diphenylethenyl)-4-ethylbenzene
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC22H19Br
Molar mass363.298 g·mol−1
3D model (JSmol)
SMILES
  • CCc1ccc(cc1)/C(=C(\c2ccccc2)/Br)/c3ccccc3
InChI
  • InChI=1S/C22H19Br/c1-2-17-13-15-19(16-14-17)21(18-9-5-3-6-10-18)22(23)20-11-7-4-8-12-20/h3-16H,2H2,1H3/b22-21+
  • Key:OQCYTSHIQNPJIC-QURGRASLSA-N

See also

References
  1. V. H. T. James; J. R. Pasqualini (22 October 2013). Proceedings of the Fourth International Congress on Hormonal Steroids: Mexico City, September 1974. Elsevier Science. pp. 223–. ISBN 978-1-4831-4566-2.
  2. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 183–. ISBN 978-1-4757-2085-3.
  3. George W.A. Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1401–1402. ISBN 978-1-351-78989-9.
  4. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 139–. ISBN 978-3-88763-075-1.
  5. Muller (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 23–. ISBN 978-3-7692-2114-5.
  6. I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 56–. ISBN 978-94-011-4439-1.
  7. Villee, Claude A.; Hagerman, Dwain D. (1957). "Compounds with Antiestrogenic Activity in Vitro1". Endocrinology. 60 (4): 552–558. doi:10.1210/endo-60-4-552. ISSN 0013-7227. PMID 13414683.
  8. Al-Hassan, Mohammed I. (1987). "Synthesis of broparestrol using palladium-catalyzed cross-coupling". Journal of Organometallic Chemistry. 321 (1): 119–121. doi:10.1016/0022-328X(87)80330-3. ISSN 0022-328X.
  9. Bentham Science Publishers (May 1994). Current Medicinal Chemistry. Bentham Science Publishers. pp. 95–.
  10. Drosdowsky M, Edery M, Guggiari M, Montes-Rendon A, Rudali G, Vives C (1980). "Inhibition of prolactin-induced mammary cancer in C3Hf (XVII) mice with the trans isomer of bromotriphenylethylene". Cancer Res. 40 (5): 1674–9. PMID 6245799.


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