Cyproterone Property

Melting point:

208-210°C

Boiling point:

521.0±50.0 °C(Predicted)

Density 

1.29±0.1 g/cm3(Predicted)

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

12.86±0.70(Predicted)

color 

Off-White to Yellow

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H351Suspected of causing cancer

H360May damage fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P281Use personal protective equipment as required.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

Cyproterone Chemical Properties,Usage,Production

Chemical Properties

White Solid

Uses

insecticide

Uses

Cyproterone is used to control sexual attraction in men in cases of sexual deviations, as well as for inoperable prostate gland carcinoma. In women, it is used for severe cases of androgenization, and in children with idiopathic premature sexual maturity.

Uses

An antiandrogen, suppresses Testosterone and its metabolites. Derivatives of Cyproterone are administered to patients suffering from hypersexuality and to help facilitate the sexual transformation of male-to-female transsexuals.

Definition

ChEBI: Cyproterone is a 20-oxo steroid, a 17alpha-hydroxy steroid, a chlorinated steroid, a 3-oxo-Delta(4) steroid and a tertiary alpha-hydroxy ketone. It has a role as an androgen antagonist. It derives from a hydride of a pregnane.

World Health Organization (WHO)

Cyproterone was introduced in the late sixties. It is an orallyactive anti-androgen with competitive inhibitory effects on androgen-sensitive target organs. It also has anti-gonadotropic and progestative properties. In 1995 the drug was found to have a hepatotoxic effect.

Synthesis

Cyproterone, 6-chloro-17|á-hydroxy-1|á,2|á-methylenpregna-4,6-dien-3,20- dione acetate (29.2.14), is made from 17|á-hydroxyprogesterone acetate (28.3.36). Dehydrating this using chloranyl (tetrachloro-p-benzoquinone) results in formation of an additional double bond at position C6¨CC7 (29.2.8), and subsequent dehydration using selenium dioxide to form the corresponding divinyl ketone, 17|á-acetoxy-1,4,6-pregnatrien- 3,20-dione (29.2.9). Reacting this with diazomethane results in a 1,3-dipolar addition reaction at C1¨CC2 of the double bond of the steroid system, which forms a derivative of dihydropyrazole (29.2.10). This compound cleaves when reacted with chloric acid, releasing nitrogen molecules and forming a cyclopropane derivative (29.1.11). Next, the double bond at C6¨CC7 is selectively oxidized by benzoyl peroxide, and the resulting epoxide (29.2.12) undergoes a reaction with hydrochloric acid in acetic acid, resulting in the formation of chlorine and its subsequent dehydration, and a simultaneous opening of the cyclopropane ring, forming the compound (29.2.13). Heating this in collidine results in intramolecular alkylation, causing cyclization into a cyclopropane ring, which forms cyproterone (29.2.14).