427-51-0 Usage
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
Different sources of media describe the Uses of 427-51-0 differently. You can refer to the following data:
1. Used as an antiandrogen. Combinded with estrogen in the treatment of acne
2. 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.
3. 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
Clinical Use
#N/A
Drug interactions
Potentially hazardous interactions with other drugs
None known
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
Check Digit Verification of cas no
The CAS Registry Mumber 427-51-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,2 and 7 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 427-51:
(5*4)+(4*2)+(3*7)+(2*5)+(1*1)=60
60 % 10 = 0
So 427-51-0 is a valid CAS Registry Number.
InChI:InChI=1/C24H29ClO4/c1-12(26)24(29-13(2)27)8-6-16-14-10-20(25)19-11-21(28)15-9-18(15)23(19,4)17(14)5-7-22(16,24)3/h10-11,14-18H,5-9H2,1-4H3/t14?,15-,16?,17?,18+,22+,23+,24+/m1/s1
427-51-0Relevant articles and documents
Preparation process of cyproterone acetate (by machine translation)
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Paragraph 0024; 0032, (2018/09/11)
The invention relates to a preparation process of cyproterone acetate, which comprises the following steps: ketal reaction; cyclopropanecarboxylic hydrolysis reaction; acetyl reaction; epoxy reaction; chlorinated reaction; a cyclization reaction; the invention can overcome the original process product is difficult to solve in the benzene remains the problem of, and the start is simple in raw material, reaction is stable, the total yield is high. (by machine translation)
KIT FOR FEMALE MAMMALS, COMPRISING A COMBINATION OF GESTAGEN AND OESTROGEN
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, (2008/06/13)
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Pharmaceutical combined preparation, kit and method for hormonal contraception
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, (2008/06/13)
PCT No. PCT/DE96/01192 Sec. 371 Date Jun. 3, 1998 Sec. 102(e) Date Jun. 3, 1998 PCT Filed Jun. 27, 1996 PCT Pub. No. WO97/01342 PCT Pub. Date Jan. 16, 1997The present invention describes a two-stage pharmaceutical combined preparation for hormonal contraception containing at least 30 daily unit doses, which preparation, in its first stage, comprises as hormonal active ingredient a combination of an oestrogen preparation and, in a dose that is at least sufficient to inhibit ovulation, a gestagen preparation, in single stage form and, in the second stage comprises as hormonal active ingredient an oestrogen preparation only, wherein the first stage comprises a minimum of 25 and a maximum of 77 daily discrete or continuous unit doses and the second stage comprises 5, 6 or 7 daily discrete or continuous unit doses, and wherein the total number of daily units is equal to the total number of days of the desired cycle of a minimum of 30 and a maximum of 84 days. This combined preparation, in the form of a monthly pack, which is used for female fertility control, permits as low as possible an oestrogen content in each individual unit dose and also has a low total hormone content per cycle of administration, with high contraceptive reliability, low incidence of follicle development, and satisfactory cycle control with reliable avoidance of intermediate bleeding as well as undesired side effects.
