2098-66-0 Usage
Description
Cyproterone is a white solid antiandrogen medication that is primarily used to suppress testosterone and its metabolites. It is effective in controlling sexual attraction in men with sexual deviations and in cases of inoperable prostate gland carcinoma. Additionally, it is utilized in women for severe androgenization and in children with idiopathic premature sexual maturity. Cyproterone and its derivatives are also administered to patients suffering from hypersexuality and to aid in the sexual transformation of male-to-female transsexuals.
Uses
Used in Pharmaceutical Industry:
Cyproterone is used as an antiandrogen for controlling sexual attraction in men with sexual deviations and in cases of inoperable prostate gland carcinoma. It helps in managing severe androgenization in women and idiopathic premature sexual maturity in children.
Used in Sexual Health:
Cyproterone is used as a therapeutic agent for patients suffering from hypersexuality, helping to regulate their sexual behavior and improve their quality of life.
Used in Transsexual Treatment:
Cyproterone is used as a hormone suppressant to facilitate the sexual transformation of male-to-female transsexuals, aiding in the process of transitioning and reducing the effects of testosterone.
Used in Insecticide Industry:
Cyproterone is also utilized as an active ingredient in insecticides, where it helps control and manage insect populations, particularly in agricultural settings.
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-17α-hydroxy-1α,2α-methylenpregna-4,6-dien-3,20-
dione acetate (29.2.14), is made from 17α-hydroxyprogesterone acetate (28.3.36).
Dehydrating this using chloranyl (tetrachloro-p-benzoquinone) results in formation of an
additional double bond at position C6–C7 (29.2.8), and subsequent dehydration using selenium dioxide to form the corresponding divinyl ketone, 17α-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–C2 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–C7 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).
Check Digit Verification of cas no
The CAS Registry Mumber 2098-66-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,9 and 8 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2098-66:
(6*2)+(5*0)+(4*9)+(3*8)+(2*6)+(1*6)=90
90 % 10 = 0
So 2098-66-0 is a valid CAS Registry Number.
InChI:InChI=1/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3/t12?,13-,14?,15?,16?,20+,21+,22+/m1/s1
2098-66-0Relevant articles and documents
Cyproterone acetate loading to lipid nanoparticles for topical acne treatment: Particle characterisation and skin uptake
Stecova, Jana,Mehnert, Wolfgang,Blaschke, Tobias,Kleuser, Burkhard,Sivaramakrishnan, Ramadurai,Zouboulis, Christos C.,Seltmann, Holger,Korting, Hans Christian,Kramer, Klaus D.,Schaefer-Korting, Monika
, p. 991 - 1000 (2008/01/27)
Purpose. Topical cyproterone acetate (CPA) treatment of skin diseases should reduce side effects currently excluding the use in males and demanding contraceptive measures in females. To improve skin penetration of the poorly absorbed drug, we intended to identify the active moiety and to load it to particulate carrier systems. Materials and Methods. CPA metabolism in human fibroblasts, keratinocytes and a sebocyte cell line as well as androgen receptor affinity of native CPA and the hydrolysis product cyproterone were determined. CPA 0.05% loaded solid lipid nanoparticles (SLN), nanostructured lipid carriers (NLC), a nanoemulsion and micropheres were characterized for drug-particle interaction and CPA absorption using human skin ex-vivo. Results. Native CPA proved to be the active agent. Application of CPA attached to SLN increased skin penetration at least four-fold over the uptake from cream and nanoemulsion. Incorporation into the lipid matrix of NLC and microspheres resulted in a 2-3-fold increase in CPA absorption. Drug amounts within the dermis were low with all preparations. No difference was seen in the penetration into intact and stripped skin. Conclusion. With particulate systems topical CPA treatment may be an additional therapeutic option for acne and other diseases of the pilosebaceous unit.
Novel 17-esters of 17α-hydroxy gestogens, compositions containing such compounds, processes for their preparation and methods of treatment therewith
-
, (2008/06/13)
This invention relates to novel 17α-esters of gestogens having an antitumour activity and to the preparation thereof. The invention is also concerned with pharmaceutical compositions containing the said compounds, and method of treatment therewith.
