Enclomifene

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Enclomifene
Enclomifene.png
Clinical data
Trade namesAndroxal
SynonymsEnclomiphene; cis-Clomifene; Cisclomiphene; (E)-Clomifene; RMI-16289; Enclomid; Enclomifene citrate; Enclomiphene citrate
Routes of
administration
By mouth
Drug classSelective estrogen receptor modulator; Progonadotropin
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC26H28ClNO
Molar mass405.966 g/mol
3D model (JSmol)

Enclomifene (INN) (tentative brand name Androxal), or enclomiphene (USAN), is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that is under development for the treatment of male hypogonadism.[1][2][3][4] As of December 2016, it is in the pre-registration phase of development and is under review by the Food and Drug Administration in the United States and the European Medicines Agency in the European Union.[3] In January 2018, the Committee for Medicinal Products for Human Use of the European Medicines Agency recommended refusal of marketing authorization for enclomifene for the treatment of secondary hypogonadism.[3]

Enclomifene acts by antagonizing the estrogen receptor (ER) in the pituitary gland, which reduces negative feedback by estrogen on the hypothalamic-pituitary-gonadal axis, thereby increasing gonadotropin secretion and hence gonadal production of testosterone.[4] It is one of the two stereoisomers of clomifene, which itself is a mixture of 38% zuclomifene and 62% enclomifene.[4] Enclomifene is the (E)-stereoisomer of clomifene, while zuclomifene is the (Z)-stereoisomer.[1][2] Whereas zuclomifene is more estrogenic, enclomifene is more antiestrogenic.[4] In accordance, unlike enclomifene, zuclomifene is antigonadotropic due to activation of the ER and is able to reduce testosterone levels in men to near-castrate levels.[4] As such, isomerically pure enclomifene is more favorable than clomifene as a progonadotropin for the treatment of male hypogonadism.[4]

See also[edit]

References[edit]

  1. ^ a b 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. ^ a b 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. ^ a b c http://webcache.googleusercontent.com/search?q=cache:rTob_FmpvpUJ:adisinsight.springer.com/drugs/800019625+&cd=1&hl=en&ct=clnk&gl=us
  4. ^ a b c d e f Hill S, Arutchelvam V, Quinton R (2009). "Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men" (PDF). IDrugs. 12 (2): 109–19. PMID 19204885.

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