Clomiphene Citrate

Chemical properties

White crystalline powder with a melting point range of 116.5-118°C. It has slight solubility in ethanol, chloroform, and water, but is insoluble in ether.

Originator

Clomid,Lepetit,Italy,1966

The Uses of Clomiphene Citrate

Selective estrogen receptor modulator, which acts by inhibiting the action of estrogen on the pituitary. Clomiphene Citrate is an activator of PKC and Gonad-stimulating principle.

The Uses of Clomiphene Citrate

Clomiphene is a selective estrogen receptor modulator that impairs the activation of estrogen receptors (ERs) by 17β-estradiol. It potently binds both ERα and ERβ (Ki = 0.9 and 1.2 nM, respectively). Clomiphene enhances the release of gonadotropin-releasing hormone, stimulating the release of follicle-stimulating hormone and luteinizing hormone, culminating in ovulation.

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

Description

Clomiphene is a medication that increases your chances of pregnancy by helping your body produce an egg (ovulation). This medication treats irregular or absent ovulation among people trying to get pregnant. The brand names of this medication are Clomid? and Serophene?.

Mechanism of action

Clomiphene citrate increases the levels of certain hormones that trigger ovulation.

Side Effects

Allergic reactions—skin rash, itching, hives, swelling of the face, lips, tongue, or throat

Change in vision

Ovarian hyperstimulation syndrome—stomach or pelvic pain, bloating, nausea, vomiting, diarrhea, weight gain

Pancreatitis—severe stomach pain that spreads to your back or gets worse after eating or when touched, fever, nausea, vomiting

Side effects that usually do not require medical attention (report to your care team if they continue or are bothersome):

Breast pain or tenderness

Headache

Hot flashes

Irregular menstrual cycles or spotting