Enclomifene

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Enclomifene
Enclomifene.png
Clinical data
Trade names Androxal
Synonyms Enclomiphene; cis-Clomifene; Cisclomiphene; (E)-Clomifene; RMI-16289; Enclomid; Enclomifene citrate; Enclomiphene citrate
Routes of
administration
Oral
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
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 FDA in the United States and the EMA in Europe.[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 non-racemic mixture of 38% zuclomifene and 62% enclomifene.[4] Enclomifene is the (E)-enantiomer of clomifene, while zuclomifene is the (Z)-enantiomer.[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, enantiopure enclomifene is more favorable than clomifene as a progonadotropin for the treatment of male hypogonadism.[4]

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