Cyproterone

Bezeichnung:Cyproterone

CAS-Nr2098-66-0

Englisch Name:Cyproterone

CBNumberCB9105300

SummenformelC22H27ClO3

Molgewicht374.9

MOL-Datei2098-66-0.mol

Cyproterone physikalisch-chemischer Eigenschaften

Schmelzpunkt	208-210°C
Siedepunkt	521.0±50.0 °C(Predicted)
Dichte	1.29±0.1 g/cm3(Predicted)
storage temp.	Refrigerator
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	12.86±0.70(Predicted)
Farbe	Off-White to Yellow

Gefahreninformationscode (GHS)

Cyproterone Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
White Solid
Verwenden
insecticide
Verwenden
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.
Verwenden
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.
Weltgesundheitsorganisation (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.
Synthese
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).

Cyproterone Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

2098-66-0, Cyproterone Verwandte Suche:

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