Clomiphene
Title: Clomiphene
CAS Registry Number: 911-45-5
CAS Name: 2-[4-(2-Chloro-1,2-diphenylethenyl)phenoxy]-N,N-diethylethanamine
Additional Names: 2-[p-(2-chloro-1,2-diphenylvinyl)phenoxy]triethylamine; 2-[p-(b-chloro-a-phenylstyryl)phenoxy]triethylamine; 1-[p-(b-diethylaminoethoxy)phenyl]-1,2-diphenylchloroethylene; clomifene; chloramiphene
Manufacturers' Codes: MRL-41; WSM-5008
Molecular Formula: C26H28ClNO
Molecular Weight: 405.96
Percent Composition: C 76.92%, H 6.95%, Cl 8.73%, N 3.45%, O 3.94%
Literature 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).
 
Derivative Type: Citrate
CAS Registry Number: 50-41-9
Trademarks: Clomid (Aventis); Clostilbegyt (Egis); Pergotime (Serono); Serofene (Serono); Serophene (Serono)
Molecular Formula: C26H28ClNO.C6H8O7
Molecular Weight: 598.08
Percent Composition: 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.
Melting point: mp 116.5-118°
 
Derivative Type: cis-Form
CAS Registry Number: 15690-55-8
Additional Names: Zuclomiphene
Properties: Hydrochloride salt mp 156.5-158.0°. uv max (methanol): 230, 291 nm (e 20500, 12700).
Melting point: mp 156.5-158.0°
Absorption maximum: uv max (methanol): 230, 291 nm (e 20500, 12700)
 
Derivative Type: trans-Form
CAS Registry Number: 15690-57-0
Additional Names: Enclomiphene
Properties: Hydrochloride salt mp 149.0-150.5°. uv max (methanol): 239, 297 nm (e 22100, 11600).
Melting point: mp 149.0-150.5°
Absorption maximum: uv max (methanol): 239, 297 nm (e 22100, 11600)
 
Therap-Cat: Gonad-stimulating principle.
Keywords: Gonad-Stimulating Principle.

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