Enclomiphene Property

Melting point:

149.0-150.5°

Boiling point:

509.0±50.0 °C(Predicted)

Density 

1.104±0.06 g/cm3(Predicted)

pka

9.60±0.25(Predicted)

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+

InChIKey

GKIRPKYJQBWNGO-OCEACIFDSA-N

SMILES

C(N(CC)CC)COC1=CC=C(/C(/C2=CC=CC=C2)=C(/Cl)\C2=CC=CC=C2)C=C1

Hazard and Precautionary Statements (GHS)

Enclomiphene Chemical Properties,Usage,Production

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.

Uses

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.