Zuclomifene

Zuclomifene

Clinical data
Other names	Zuclomiphene; 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	15690-55-8
PubChem CID	1548955
ChemSpider	1265969
UNII	3JU1DU3652
KEGG	D09037
CompTox Dashboard (EPA)	DTXSID601317947
Chemical and physical data
Formula	C26H28ClNO
Molar mass	405.97 g·mol−1
3D model (JSmol)	Interactive image
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

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]

References

1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 298–. ISBN   978-1-4757-2085-3.
2. Morton IK, Hall JM (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". AdisInsight. Springer Nature Switzerland AG.
4. Hill S, Arutchelvam V, Quinton R (February 2009). "Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men". IDrugs. 12 (2): 109–119. PMID   19204885.
5. Luniwal A, Jetson R, Erhardt P (15 October 2012). "Selective Estrogen Receptors Modulators". In Fischer J, Ganellin CR, Rotella DP (eds.). Analogue-based Drug Discovery III. John Wiley & Sons. pp. 5–. ISBN   978-3-527-65110-8.