2386. Clomiphene

Nomenclature

CAS number: 911-45-5
2-[4-(2-Chloro-1,2-diphenylethenyl)phenoxy]-N,N-diethylethanamine; 2-[p-(2-chloro-1,2-diphenylvinyl)phenoxy]triethylamine; 2-[p-(β-chloro-α-phenylstyryl)phenoxy]triethylamine; 1-[p-(β-diethylaminoethoxy)phenyl]-1,2-diphenylchloroethylene; clomifene; chloramiphene; MRL-41; WSM-5008.
C26H28ClNO; mol wt 405.96.
C 76.92%, H 6.95%, Cl 8.73%, N 3.45%, O 3.94%.

Description and references

Synthetic estrogen agonist-antagonist. Prepn: R. E. Allen et al., US 2914563 (1959 to Merrell); F. P. Palopoli et al., J. Med. Chem. 10, 84 (1967). Stereochemistry of the geometric isomers: Ernst et al., J. Pharm. Sci. 65, 148 (1976). Induction of ovulation: R. B. Greenblatt, Fertil. Steril. 12, 402 (1961). Clinical trial in anovulatory women: J. Garcia et al., ibid. 28, 707 (1977). Use in male infertility: P. J. Sorbie, R. Perez-Marrero, J. Urol. 131, 425 (1984). HPLC determn of isomers in human plasma: C. L. Baustian, T. J. Mikkelson, J. Pharm. Biomed. Anal. 4, 237 (1986). Review of development, pharmacology and clinical experience: R. P. Dickey, D. E. Holtkamp, Hum. Reprod. Update 2, 483-506 (1996).

Chemical structure

Derivative

Citrate.

Nomenclature

CAS number: 50-41-9
Clomid (Aventis); Clostilbegyt (Egis); Pergotime (Serono); Serofene (Serono); Serophene (Serono).
C26H28ClNO.C6H8O7; mol wt 598.08.
C 64.26%, H 6.07%, Cl 5.93%, N 2.34%, O 21.40%.

Properties

Crystals, mp 116.5-118°. Slightly sol in water, chloroform; freely sol in methanol; sparingly sol in alcohol. Insol in ether.

Derivative

cis-Form.

Nomenclature

CAS number: 15690-55-8
Zuclomiphene.

Properties

Hydrochloride salt mp 156.5-158.0°. uv max (methanol): 230, 291 nm (ε 20500, 12700).

Derivative

trans-Form.

Nomenclature

CAS number: 15690-57-0
Enclomiphene.

Properties

Hydrochloride salt mp 149.0-150.5°. uv max (methanol): 239, 297 nm (ε 22100, 11600).

Therapeutic Category

Gonad-stimulating principle.

Keywords

Gonad-Stimulating Principle