Broparestrol

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−1
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^[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]

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. ^ ^{a b} 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. ^ ^{a b} 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. ^ ^{a b} 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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