| Name | Cyproterone Acetate |
|---|---|
| Synonyms | cyprosteroneacetate; 1,2-alpha-methylene-6-chloro-delta-(sup4,6)-pregnadiene-17-alpha-ol-3,20-dio; 1,2-alpha-methylene-6-chloro-delta(sup6)-17-alpha-hydroxyprogesteroneacetat; 1,2-alpha-methylene-6-chloro-pregna-4,6-diene-3,20-dione17-alpha-acetate; 17-alpha-acetoxy-6-chloro-1-alpha,2-alpha-methylenepregna-4,6-diene-3,20-dio; 20-dione,6-chloro-17-hydroxy-1-alpha,2-alpha-methylene-pregna-6-diene-3; 6)-pregnadiene-17-alpha-ol-3,20-dione17-2-alpha-methylene-6-chloro-(sup4; 6-chlor-delta(sup6)-1,2-alpha-methylen-17-alpha-hydroxyprogesteronacetat SH-714 ANDROCUR CYPROSTAT nsc-81430 Cyproviron Androcurone acetate cyproteron-racetate cyprosteroneacetate CYPROTERONE ACETATE CYPROFERONE ACETATE CIPROTERONE ACETATE Androcur, Cyprostat CyproteroneAcetateEdmf CyproteroneAcetateedmfep5 cyproterone17-alpha-acetate * Color Pronk (cyproterone) Cyproterone acetate(Androcur) Cyproterone Acetate BP2000,EP2000 Cyproterone acetate for peak identification 6-Chloro-1α,2α-methylene-3,20-dioxopregna-4,6-dien-17-yl acetate 20-dione,6-chloro-17-hydroxy-1-alpha,2-alpha-methylene-pregna-6-diene-3 6)-pregnadiene-17-alpha-ol-3,20-dione17-2-alpha-methylene-6-chloro-(sup4 6-chlor-delta(sup6)-1,2-alpha-methylen-17-alpha-hydroxyprogesteronacetat 1,2-alpha-methylene-6-chloro-pregna-4,6-diene-3,20-dione17-alpha-acetate 6-chloro-1,2-alpha-methylene-6-dehydro-17-alpha-hydroxyprogesteroneacetate 6-chloro-delta(sup6)-1,2-alpha-methylene-17-alpha-hydroxyprogesteroneacetat 1,2-alpha-methylene-6-chloro-delta(sup6)-17-alpha-hydroxyprogesteroneacetat 6-chloro-1,2-alpha-methylene-17-alpha-hydroxy-delta(sup6)-progesteroneaceta 4,6-PREGNADIEN-6-CHLORO-1-ALPHA, 2-ALPHA-METHYLENE-17-OL-3,20-DIONE ACETATE 1,2-alpha-methylene-6-chloro-delta-(sup4,6)-pregnadiene-17-alpha-ol-3,20-dio 17-alpha-acetoxy-6-chloro-1-alpha,2-alpha-methylenepregna-4,6-diene-3,20-dio 6-chloro-17-hydroxy-1-alpha,2-alpha-methylenepregna-4,6-diene-3,20-dioneacet 6-Chloro-1β,2β-dihydro-17-hydroxy-3μH-cyclopropa(1,2)-pregna-1,4,6-triene-3,20-dione acetate (1β,2β)-17-(acetyloxy)-6-chloro-1,2-dihydro-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione 6-chloro-1b,2b-dihydro-17-hydroxy-3'h-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione 17-acetate 6-CHLORO-1BETA,2BETA-DIHYDRO-17-HYDROXY-3'H-CYCLOPROPA[1,2]-PREGNA-1,4,6-TRIENE-3,20-DIONE ACETATE 6-chloro-1-beta,2-beta-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione 17-acetate 3H-Cyclopropa1,2pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-6-chloro-1,2-dihydro-, (1.beta.,2.beta.)- |
| CAS NO | 427-51-0 |
| EINECS | 207-048-3 |
| Molecular Weight | 416.94 |
| Molecular Formula | C24H29ClO4 |
| Product Categories | Intracellular receptor; Antibiotics; Steroids; Intermediates & Fine Chemicals; Pharmaceuticals; Steroid and Hormone; VETRANAL; Hormone Drugs |
| Mol File | 427-51-0.mol |
Cyproterone acetate Chemical Properties | |
|---|---|
| Melting point | 200-201°C |
| Boiling point | 528.8°C (rough estimate) |
| density | 1.0677 (rough estimate) |
| storage temp | 2-8°C |
| refractive index | 1.4429 (estimate) |
| solubility | Practically insoluble in water, very soluble in methylene chloride, freely soluble in acetone, soluble in methanol, sparingly soluble in anhydrous ethanol. |
| form | neat |
| λmax | 281nm(MeOH)(lit.) |
| Merck | 14,2774 |
| EPA Substance Registry System | 3'H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-6-chloro-1,2-dihydro-, (1.beta.,2.beta.)- (427-51-0) |
| Safety Information | |
|---|---|
| Hazard Codes | Xn,Xi |
| Risk Statements | 20/21/22-40-36/37/38 |
| Safety Statements | 22-36-26 |
| WGK Germany | 3 |
| RTECS | GZ2230000 |
| HS Code | 29372900 |
| Hazardous Substances Data | 427-51-0(Hazardous Substances Data) |
| Cyproterone acetate Usage And Synthesis | |
|---|---|
| Chemical Properties | Crystalline Solid |
| Originator | Androcur ,Schering,W. Germany,1973 |
| Uses | Used as an antiandrogen. Combinded with estrogen in the treatment of acne |
| Uses | The free alcohol is an anti-androgen; cyproterone acetate is both an anti-androgen and a progestogen. Combined with estrogen it is used in the treatment of acne. |
| Uses | antiparasitic, fasciolicide |
| Indications | Cyproterone acetate is a progestational antiandrogen that blocks androgen receptor binding and suppresses androgen-sensitive tissues. It is available in a topical form in Europe for the treatment of hirsutism. |
| Manufacturing Process | 2.34 g of 1,2α-methylene-δ4,6-pregnadiene-17α-ol-3,20-dione-17-acetate are dissolved in 18.25 cc of ethylene chloride which contains 844 rng of perbenzoic acid. The solution is stored for 16 hours at +5°C and 7 hours at room temperature. It is then diluted with methylene chloride and, with aqueous ferrous sulfate solution, sodium bicarbonate solution and with water washed until neutral. The organic phase is dried over sodium sulfate and then concentrated to dryness. 1.62 g of the thus obtained crude 1,2α-methylene-6,7α-oxido-δ4- pregnene-17α-ol-3,20-dione-17-acetate are dissolved in 109 cc of glacial acetic acid. This solution is then saturated at room temperature with hydrogen chloride gas and stored for 20 hours, It is then diluted with methylene chloride and washed with water until neutral. The organic phase is dried over sodium sulfate and then concentrated to dryness. The thus obtained crude 6-chloro-1α-chloromethyl-δ4,6-pregnadiene17α-ol-3,20-dione-17-acetate is heated to boiling in 20 cc of collidine for 20 minutes under nitrogen. After dilution with ether it is washed with 4 N hydrochloric acid and washed with water until neutral. After drying over sodium sulfate and concentration to vacuum the remaining residue is subjected to chromatography over silica gel. Using a benzene-ethyl acetate mixture (19:1) there is eluated 900 mg of 6-chloro-1,2α-methyleneδ4,6-pregnadiene-17α-ol-3,20-dione-17-acetate, which upon recrystallization from isopropyl ether melts at 200° to 201°C. |
| Therapeutic Function | Antiandrogen |
| Cyproterone acetate Preparation Products And Raw materials | |
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