Enclomiphene

Description

Enclomiphene is a synthetic and nonsteroidal antiestrogen. It is the more potent isomer and the one responsible for its ovulation-inducing actions. The half-life of enclomiphene is relatively short, so serum concentrations rise and fall quickly during and after treatment. Antiestrogens represent the first-line treatment strategy in WHO class-2 anovulatory infertility.

The Uses of Enclomiphene

trans-Clomiphene is a Clomiphene (C587025) stereoisomer, a synthetic estrogen agonist-antagonist. Gonad-stimulating principle. Treatment for infertility.

Definition

ChEBI: Clomiphene is a tertiary amine. It has a role as an estrogen antagonist and an estrogen receptor modulator. It derives from a hydride of a stilbene.

Preparation

CONDENSATION OF 4-HYDROXYBENZOPHENONE WITH 2-(DIETHYLAMINO)ETHYL CHLORIDE FOLLOWED BY TREATMENT WITH BENZYL MAGNESIUM CHLORIDE AND DEHYDRATION TO GIVE 2-(P-(1,2-DIPHENYLVINYL)PHENOXY)TRIETHYLAMINE WHICH IS CHLORINATED AND TREATED WITH CITRIC ACID /CITRATE/

Biological Activity

Enclomiphene is the trans-isomer of clomiphene citrate (CC). It has a higher rate of clearance and is less active than the cis-isomer, cis-clomiphene. Clomiphene citrate has been evaluated for antineoplastic activity against breast cancer.

Mode of action

Enclomiphene is a non-steroidal estrogen receptor antagonist that promotes gonadotropin-dependent testosterone secretion by the testes. The main mechanism of its action is thought to be its antagonistic effects on the hypothalamic-pituitary axis and stimulation of GnRH secretion.

References

[1] SIMON HILL Richard Q Vijayaraman Arutchelvam. Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men.[J]. Idrugs, 2009, 12 2: 109-119.
[2] KATHERINE M RODRIGUEZ Larry I L Alexander W Pastuszak. Enclomiphene citrate for the treatment of secondary male hypogonadism.[J]. Expert Opinion on Pharmacotherapy, 2016, 17 11: 1561-1567. DOI:10.1080/14656566.2016.1204294.
[3] JOSHUA A EARL Edward D K. Enclomiphene citrate: A treatment that maintains fertility in men with secondary hypogonadism.[J]. Expert Review of Endocrinology & Metabolism, 2019, 14 3: 157-165. DOI:10.1080/17446651.2019.1612239.