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Cyproterone acetate(CAS No. 427-51-0)

Cyproterone acetate C24H29ClO4 (cas 427-51-0) Molecular Structure

427-51-0 Structure

Identification and Related Records

【Name】
Cyproterone acetate
【CAS Registry number】
427-51-0
【Synonyms】
SH 714
Cyproteron-r acetate
6-Chloro-1beta,2beta-dihydro-17-hydroxy-3H-cyclopropa(1,2)-pregna-1,4,6-triene-3,20-dione acetate
Cyproteroneacetate
Cyproterone acetate (JAN/USAN)
Cyproviron
1,2-alpha-Methylene-6-chloro-(sup 4,6)-pregnadiene-17-alpha-ol-3,20-dione 17-alpha-acetate
6-Chloro-delta(sup 6)-1,2-alpha-methylene-17-alpha-hydroxyprogesterone acetate
3H-Cyclopropa[1,2]pregna-1,4,6-triene-3, 20-dione, 17- (acetyloxy)-6-chloro-1,2-dihydro-, (1.beta., 2.beta.)-
6-Chloro-delta-6-1,2alpha-methylene-17alpha-hydroxyprogesterone acetate
17-alpha-Acetoxy-6-chloro-1-alpha,2-alpha-methylenepregna-4,6-diene-3,20-dione
1,2-alpha-Methylene-6-chloro-pregna-4,6-diene-3,20-dione 17-alpha-acetate
Cyproterone acetate [USAN:JAN]
Cyproterone 17-O-acetate
6-Chloro-1-beta,2-beta-dihydro-17-hydroxy-3H-cyclopropa(1,2)pregna-1,4,6-triene-3,20-dione 17-acetate
SH 80714
3H-Cyclopropa(1,2)pregna-1,4,6-triene-3,20-dione, 6-chloro-1-beta,2-beta-dihydro-17-hydroxy-, acetate
6-Chloro-17-hydroxy-1.alpha.,2.alpha.-methylenepregna-4, 6-diene-3,20-dione acetate
Pregna-4,6-diene-3,20-dione, 6-chloro-17-hydroxy-1.alpha.,2.alpha.-methylene-, acetate
Cyproterone 17.alpha.-acetate
1, 2.alpha.-Methylene-6-chloro-(sup 4,6)-pregnadiene-17.alpha.-ol-3, 20-dione 17alpha-acetate
Progesterone, 6-chloro-6-dehydro-17-hydroxy-1.alpha.,2.alpha.-methylene-, acetate
Cyproterone 17alpha-acetate
3'H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20- dione,17-(acetyloxy)-6-chloro-1,2-dihydro-,(1a,2a)-
Cyproteron acetate
Cyprosterone acetate
Androcur
6-chloro-1-β,2-β-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione 17-acetate
【EINECS(EC#)】
207-048-3
【Molecular Formula】
C24H29ClO4 (Products with the same molecular formula)
【Molecular Weight】
416.94
【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-/m0/s1
【Canonical SMILES】
CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(=O)C5CC5C34C)Cl)C)OC(=O)C
【Isomers smiles】
CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=C(C4=CC(=O)[C@@H]5C[C@@H]5
[C@]34C)Cl)C)OC(=O)C
【MOL File】
427-51-0.mol

Chemical and Physical Properties

【Appearance】
Odour
【Density】
1.27 g/cm3
【Melting Point】
200-201oC
【Boiling Point】
525.9oC at 760 mmHg
【Vapour】
3.78E-11mmHg at 25°C
【Refractive Index】
1.582
【Flash Point】
177.6 oC
【Solubilities】
Practically insoluble in water; very soluble in dichloromethane and acetone; soluble in methanol; sparingly soluble in ethanol.
【Color/Form】
Crystals from diisopropyl ether.
White crystalline powder
【Storage temp】
2-8°C
【Spectral properties】
UV max (methanol): 281 nm
Specific rotation= +152 deg to +157 deg @ 20 deg C
【Computed Properties】
Molecular Weight:416.93766 [g/mol]
Molecular Formula:C24H29ClO4
XLogP3-AA:3.6
H-Bond Donor:0
H-Bond Acceptor:4
Rotatable Bond Count:3
Tautomer Count:10
Exact Mass:416.175437
MonoIsotopic Mass:416.175437
Topological Polar Surface Area:60.4
Heavy Atom Count:29
Formal Charge:0
Complexity:903
Isotope Atom Count:0
Defined Atom Stereocenter Count:8
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Ring Count:4
Effective Rotor Count:4.2
Conformer Sampling RMSD:0.8
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R20/21/22;R40
【Safety Statements 】
S26;S36
【Safety】

Safety Information of Cyproterone acetate (CAS NO.427-51-0):
Hazard Codes:Xn,Xi  
Risk Statements:20/21/22-40-36/37/38
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
40:Limited evidence of a carcinogenic effect 
36/37/38:Irritating to eyes, respiratory system and skin  
Safety Statements:22-36-26
22:Do not breathe dust
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice    
WGK Germany:3
RTECS:GZ2230000
Hazardous Substances Data:427-51-0(Hazardous Substances Data)
Questionable carcinogen with experimental tumorigenic and teratogenic data. Moderately toxic by intraperitoneal route. Human reproductive effects by ingestion and possibly other routes: abnormal spermatogenesis, changes in the testes, epididymis, and sperm duct, impotence, and other paternal effects. Experimental reproductive effects. Mutation data reported. Used as a drug to arrest precocious puberty in children and hirsutism in women. A steroid. When heated to decomposition it emits toxic fumes of Cl.

【Formulations/Preparations】
...commercially available as tablets and as an injectable solution.
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
【Specification】

Crystalline Solid
usageEng:Used as an antiandrogen. Combinded with estrogen in the treatment of acne
Safety Statements:22-36-26
22:Do not breathe dust
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
【Report】

EPA Genetic Toxicology Program.

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Usage】
Used as an antiandrogen. Combinded with estrogen in the treatment of acne

Biomedical Effects and Toxicity

【Pharmacological Action】
- Compounds which inhibit or antagonize the biosynthesis or actions of androgens.
- Substances that inhibit or prevent the proliferation of NEOPLASMS.
- Chemical substances or agents with contraceptive activity in males. Use for male contraceptive agents in general or for which there is no specific heading.
【Therapeutic Uses】
Androgen Antagonists; Antineoplastic Agents; Contraceptive Agents, Male; Progestational Hormones, Synthetic
The drug is used for the treatment of prostatic carcinoma in Europe.
Cyproterone acetate has a strong gonadotropin-inhibiting effect and has clinical use as an anti-androgen for the treatment of hyperandrogenic disorders such as hirsutism, acne and seborrhea in women. It is used as an oral contraceptive in combination with ethinylestradiol. It is given in combination with estradiol valerate to women over 35 up to the climacteric because its effects on the coagulation system are minimal. Cyproterone acetate is also used in the treatment of prostate cancer and hypersexuality disorders and is being investigated as a means of oral contraception in men.
The administration of 100 mg per day of cyproterone acetate to normal young men causes a 50% decrease in plasma concentrations of LH and FSH and a 75% decrease in plasma testosterone; the effects of the drug result both from inhibition of testosterone production and from interference with androgen action ... . The agent has been used for the treatment of acne, male pattern baldness, hirsutism, and virilizing syndromes ... . It also has been tried in the treatment of precocious puberty ... and prostatic hyperplasia and carcinoma ... and to inhibit libido in men with severe deviations of sexual behavior... . Although cyproterone acetate is still under investigation, the agent has orphan drug status in the United States for the treatment of severe hirsutism.
Progesterone itself is a weak antiandrogen, and in the search for orally active progestogens, cyproterone acetate was found to be a potent androgen antagonist ... . Cyproterone acetate also possesses progestational activity and suppresses the secretion of gonadotropins ... . The agent competes with dihydrotestosterone for binding to the androgen receptor ...; when given to pregnant animals, cyproterone acetate blocks the actions of androgen in the male fetus and hence induces a form of male pseudohermaphroditism ... . In the castrated animal, the antagonist, at a dose about five times that of testosterone, reduces the androgenic response by about 50%; with larger doses of cyproterone acetate, the antagonism is almost complete ... .
The development of the androgen, cyproterone acetate provided a new alternative for prostate cancer therapy. originally developed as a synthetic progestin for use as an oral contraceptive, the antiandrogenic action of this agent was identified by the feminization of the offspring it induced after administration to gestating female rats.
【Biomedical Effects and Toxicity】
A group of eight young women were treated with a single oral dose of 100 mg cyproterone acetate followed by a single intramuscular dose of 300 mg four weeks later, and the plasma concentration of both parent compound and the 15beta-hydroxy metabolite were quantified in seven of the women. The bioavailability of cyproterone acetate after oral administration was about 88%; the mean maximum serum concentration reached 255 ng/ml after two to three days and then declined, with a half-life of about 4.3 days. The serum concentrations of the 15beta-hydroxymetabolite exceeded those of the parent compound 6 hours after oral administration and four days after intramuscular injection. Thereafter, the concentration of the 15beta-hydroxy metabolite decreased at a rate parallel to that of cyproterone acetate, indicating that the formation of this metabolite was the rate-limiting metabolic step.
A group of 15 women were treated with a single oral dose of 2.0 mg cyproterone acetate plus 0.035 mg ethinylestradiol. After one week, three cycles of multiple treatments were started with the same preparation. After the single dose, the maximum concentration of cyproterone acetate was 15.2 ng/ml, which decreased biphasically with half-lives of 0.8 and 54 hours, respectively; 3.5% of the dose was free, while 96.5% was bound to serum proteins. During the multiple treatment cycles, a twofold higher accumulation of cyproterone acetate was observed, and its half-life increased to 78 hours.

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