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Clinical data
Trade names Androxal
Synonyms Enclomiphene; cis-Clomifene; Cisclomiphene; (E)-Clomifene; RMI-16289; Enclomid; Enclomifene citrate; Enclomiphene citrate
Routes of
By mouth
Drug class Selective estrogen receptor modulator; Progonadotropin
CAS Number
PubChem CID
Chemical and physical data
Formula C26H28ClNO
Molar mass 405.966 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]

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