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Broparestrol

From Wikipedia, the free encyclopedia
(Redirected fromLN-1643)
Chemical compound
Pharmaceutical compound
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
  • 1-(2-bromo-1,2-diphenylethenyl)-4-ethylbenzene
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC22H19Br
Molar mass363.298 g·mol−1
3D model (JSmol)
  • CCc1ccc(cc1)/C(=C(\c2ccccc2)/Br)/c3ccccc3
  • 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 namesAcnestrol,Longestrol; former developmental code nameLN-107), also known asα-bromo-α,β-diphenyl-β-p-ethylphenylethylene (BDPE), is asynthetic,nonsteroidalselective estrogen receptor modulator (SERM) of thetriphenylethylene group[1] that has been used inEurope as adermatological agent and for the treatment ofbreast cancer.[2][3][4][5][6] The drug is described as slightlyestrogenic[7] and potentlyantiestrogenic,[8][9] and inhibitsmammary gland development and suppressesprolactin levels in animals.[10] It is structurally related toclomifene anddiethylstilbestrol.[6][10] Broparestrol is a mixture ofE- andZ-isomers (LN-1643 and LN-2299, respectively), both of which are active, and are similarly antiestrogenic but, unlike broparestrol, were never marketed.[2]

See also

[edit]

References

[edit]
  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. ^abElks 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. ^abMorton 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. ^abDrosdowsky 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.
Estrogens
ERTooltip Estrogen receptor agonists
Progonadotropins
Antiestrogens
ERTooltip Estrogen receptor antagonists
(incl.SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)
Aromatase inhibitors
Antigonadotropins
Others
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
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