Zuclomifene

Zuclomifene (INN; or zuclomiphene (USAN)) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was never marketed.[1][2][3][4] It is one of the two stereoisomers of clomifene, which itself is a mixture of 38% zuclomifene and 62% enclomifene.[4] Zuclomifene is the (Z)-stereoisomer of clomifene, while enclomifene is the (E)-stereoisomer.[1][2] Whereas zuclomifene is described as mildly estrogenic, enclomifene is described as antiestrogenic.[4][5] In accordance, unlike enclomifene, zuclomifene is antigonadotropic due to activation of the estrogen receptor and reduces testosterone levels in men.[4] It is also about five times more potent than enclomifene in inducing ovulation.[5]

Zuclomifene
Clinical data
Other namesZuclomiphene; trans-Clomifene; Transclomiphene; (Z)-Clomifene; ICI-46476; RMI-16312; Zuclomifene citrate; Zuclomiphene citrate
Routes of
administration		Oral
Identifiers
IUPAC name
  • 2-[4-[(Z)-2-Chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC26H28ClNO
Molar mass405.97 g·mol−1
3D model (JSmol)
SMILES
  • CCN(CC)CCOC1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\Cl)/C3=CC=CC=C3
InChI
  • InChI=1S/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3/b26-25-
  • Key:GKIRPKYJQBWNGO-QPLCGJKRSA-N

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 298–. ISBN 978-1-4757-2085-3.
  2. I.K. Morton; Judith M. Hall (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 79–. ISBN 978-0-7514-0499-9.
  3. "Enclomifene - Repros Therapeutics". Adis Insight.
  4. Hill S, Arutchelvam V, Quinton R (2009). "Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men". IDrugs. 12 (2): 109–19. PMID 19204885.
  5. Janos Fischer; C. Robin Ganellin; David P. Rotella (15 October 2012). Analogue-based Drug Discovery III. John Wiley & Sons. pp. 5–. ISBN 978-3-527-65110-8.


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