Clomifene Property

Melting point:

117.25°C

Boiling point:

509.0±50.0 °C(Predicted)

Density 

1.0166 (rough estimate)

refractive index 

1.5790 (estimate)

storage temp. 

Amber Vial, -20°C Freezer

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.54±0.25(Predicted)

color 

White to Pale Yellow

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

InChIKey

GKIRPKYJQBWNGO-UHFFFAOYSA-N

SMILES

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

NIST Chemistry Reference

Clomiphene(911-45-5)

EPA Substance Registry System

Clomiphene (911-45-5)

Safety

Hazardous Substances Data

911-45-5(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Clomifene Chemical Properties,Usage,Production

Description

Clomiphene is an antiestrogen thought to increase sperm parameters in males attempting to conceive. The objective of this review was to evaluate the efficacy and safety of Clomiphene citrate in the treatment of male patients with infertility. It is an oral agent used to treat infertility in women desiring pregnancy. Clomiphene has been linked to a low rate of transient serum aminotransferase elevations during therapy and to rare instances of clinically apparent liver injury, which can be severe and even fatal.A triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue.

Hormonal modulation

CLOMIPHENE exerts its effects centrally with a result of increased LH and FSH secretion and increased testicular testosterone production. Many studies have described significant increases in serum testosterone, LH, and FSH with CLOMIPHENE treatment. Studies have revealed comparable increases in serum testosterone levels in hypogonadal men treated with CLOMIPHENE compared with TRT. CLOMIPHENE has also been compared with aromatase inhibitors, such as anastrozole, and CLOMIPHENE has proven to be more effective in increasing testosterone levels.

Originator

Clomid,Lepetit,Italy,1966

Uses

Clomifene is used for infertility in order to increase reproductive properties of oligoovulatory women who have three or four ovulatory cycles per year, leading to normal monthly ovulation.

Uses

Antiestrogen.

Indications

Clomifene acts by enhancing follicular growth caused by ovulation. The primary indication for using clomifene is induction of ovulation in non-ovulating women who still have some estrogen production.

Definition

ChEBI: Zuclomifene is a stilbenoid.

Manufacturing Process

A mixture of 20 g of 1-[p-(β-diethylaminoethoxy)phenyl]-1,2-diphenylethanol in 200 cc of ethanol containing an excess of hydrogen chloride was refluxed 3 hours. The solvent and excess hydrogen chloride were removed under vacuum, and the residue was dissolved in a mixture of ethyl acetate and methylene chloride. 1-[p-(β-diethylaminoethoxy)phenyl]-1,2-diphenylethylene hydrochloride was obtained, melting at 148° to 157°C. This hydrochloride salt was treated with N-chlorosuccinimide in dry chloroform under reflux. The product then obtained was converted to the free base and treated with citric acid. The dihydrogen citrate salt of 1-[p-(β-diethylaminoethoxy)phenyl]-1,2- diphenylchloroethylene was obtained, melting at 116.5° to 118°C.
The intermediate 1-[p-(β-diethylaminoethoxy)phenyl]-1,2-diphenylethanol was obtained by treating 4-(β-diethylaminoethoxy)benzophenone with benzylmagnesium chloride. It melted at 95° to 96°C.

brand name

Clomid (Sanofi Aventis); Serophene (Serono).

Therapeutic Function

Antiestrogen

Synthesis

Clomifene, 2-[p-(2-chloro-1,2-diphenylvinyl)phenoxy]triethylamine (28.2.4), is synthesized from 4-hydroxybenzophenone by reacting it with 2-diethylaminoethylchloride in the presence of an alkali, which gives 4-(2-diethylaminoethoxy)benzophenone (28.2.1). This is reacted with benzylmagnesium chloride in a Grignard reaction, forming as a result the corresponding carbinol (28.2.2). Dehydrating this with hydrogen chloride gives 2-[p-(1,2-diphenylvinyl) phenoxy]triethylamine (28.2.4), the vinylic hydrogen atom of which is replaced with a chlorine atom using N-chlorosuccinimide, giving clomifene (28.2.4) .