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Broparestrol

Clinical data
Trade names	Acnestrol, Longestrol
Other names	LN-107; α-Bromo-α,β-diphenyl-β-p-ethylphenylethylene; BDPE
Pregnancy category	X (Contraindicated)
Routes of administration	By mouth
Drug class	Selective estrogen receptor modulator
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 1-(2-bromo-1,2-diphenylethenyl)-4-ethylbenzene
CAS Number	479-68-5 Z-isomer: 22393-63-1
PubChem CID	3032769
ChemSpider	2297663
UNII	4F4UXV47YI Z-isomer: D6CYJ2NI2L
CompTox Dashboard (EPA)	DTXSID201203500
Chemical and physical data
Formula	C22H19Br
Molar mass	363.298 g·mol
3D model (JSmol)	Interactive image
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

Broparestrol (INNTooltip International Nonproprietary Name) (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 that has been used in Europe as a dermatological agent and for the treatment of breast cancer. The drug is described as slightly estrogenic and potently antiestrogenic, and inhibits mammary gland development and suppresses prolactin levels in animals. It is structurally related to clomifene and diethylstilbestrol. 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.

See also

• List of selective estrogen receptor modulators

References

1. Hospital M, Busetta B, Courseille C, Precigoux G (1975). "X-ray conformation of some estrogens and their binding to uterine receptors". Journal of Steroid Biochemistry. 6 (3–4): 221–5. doi:10.1016/0022-4731(75)90136-3. PMID 171486.
2. ^ Elks J (14 November 2014). "Broparestrol". The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 183–. ISBN 978-1-4757-2085-3.
3. Milne GW (8 May 2018). "Broparestrol". Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1401–1402. ISBN 978-1-351-78989-9.
4. "Broparestrol". 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 ed.). CRC Press. pp. 23–. ISBN 978-3-7692-2114-5.
6. ^ Morton IK, Hall JM (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 CA, Hagerman DD (April 1957). "Compounds with antiestrogenic activity in vitro". Endocrinology. 60 (4): 552–558. doi:10.1210/endo-60-4-552. 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. Magarian RA, Overacre LB, Singh S, Meyer KL (1994). "The medicinal chemistry of nonsteroidal antiestrogens: a review". Current Medicinal Chemistry. 1: 61-104 (95). doi:10.2174/0929867301666220210212635. S2CID 89392480.
10. ^ Drosdowsky M, Edery M, Guggiari M, Montes-Rendon A, Rudali G, Vives C (May 1980). "Inhibition of prolactin-induced mammary cancer in C3Hf (XVII) mice with the trans isomer of bromotriphenylethylene". Cancer Research. 40 (5): 1674–1679. PMID 6245799.

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