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| | Cyproterone acetate Basic information |
| Product 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 | | CAS: | 427-51-0 | | MF: | C24H29ClO4 | | MW: | 416.94 | | EINECS: | 207-048-3 | | Product Categories: | Intracellular receptor;Antibiotics;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;Steroid and Hormone;VETRANAL;Hormone Drugs;427-51-0 | | 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) | | refractive index | 1.4429 (estimate) | | storage temp. | Sealed in dry,Store in freezer, under -20°C | | solubility | Practically insoluble in water, very soluble in methylene chloride, freely soluble in acetone, soluble in methanol, sparingly soluble in anhydrous ethanol. | | form | neat | | color | White to Off-White | | 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) |
| | Cyproterone acetate Usage And Synthesis |
| Description | Cyproterone acetate (CPA) is an androgen receptor antagonist. It binds to human androgen receptors (Ki = 14 nM) and inhibits dihydrotestosterone-induced androgen receptor activation in CV-1 cells (IC50 = 26 nM). CPA (30 mg/kg) decreases ventral prostate weight in castrated immature rats. It also suppresses accessory sexual glands and fertility in adult male rats when administered at a dose of 10 mg/kg. CPA (0.3 μM) also induces apoptosis in primary adult female rat hepatocytes. Formulations containing cyproterone acetate have been used in the treatment of androgenization in females. | | 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. | | Definition | ChEBI: Cyproterone acetate is a steroid ester resulting from the formal condensation of the carboxy group of acetic acid with the 17-hydroxy group of cyproterone. It is an antiandrogenic drug which has recently been recognized to promote the occurrence and growth of intracranial meningiomas. It has a role as an androgen antagonist, a progestin and a geroprotector. It is a 20-oxo steroid, a 3-oxo-Delta(4) steroid, a chlorinated steroid, a steroid ester and an acetate ester. It is functionally related to a cyproterone. | | 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 | | Metabolism | Cyproterone is metabolised by various pathways including
hydroxylation and conjugation; about 35% of a dose is
excreted in urine, the remainder being excreted in the bile.
The principal metabolite, 15β-hydroxycyproterone, has
anti-androgenic activity |
| | Cyproterone acetate Preparation Products And Raw materials |
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