CAS 427-51-0

Cyproterone acetate

Description:

Cyproterone acetate is a synthetic steroidal anti-androgen and progestin, primarily used in the treatment of conditions such as androgen-dependent disorders, including hirsutism and acne, as well as in hormone therapy for transgender women. It functions by blocking the effects of androgens, such as testosterone, at the receptor level, and also exhibits progestational activity. The compound is characterized by its chemical formula C22H27ClO3 and a molecular weight of approximately 403.91 g/mol. Cyproterone acetate is typically administered orally and is known for its relatively high bioavailability. It is soluble in organic solvents like ethanol and chloroform but has limited solubility in water. The substance is often formulated in various dosage forms, including tablets and injectable solutions. Side effects may include weight gain, mood changes, and potential impacts on liver function, necessitating monitoring during treatment. Due to its hormonal activity, cyproterone acetate is contraindicated in certain populations, including pregnant individuals.

Formula: C₂₄H₂₉ClO₄

InChI: InChI=1S/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

InChI key: InChIKey=UWFYSQMTEOIJJG-FDTZYFLXSA-N

SMILES: C[C@]12[C@@]3([C@@](C3)(C(=O)C=C1C(Cl)=C[C@@]4([C@@]2(CC[C@@]5(C)[C@]4(CC[C@]5(OC(C)=O)C(C)=O)[H])[H])[H])[H])[H]

Synonyms:

• (1R,7aR,8aS,8bS,10aS)-1-acetyl-5-chloro-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,7,7a,8,8a,8b,8c,9,10,10a-tetradecahydrocyclopenta[a]cyclopropa[g]phenanthren-1-yl acetate
• (1β,2β)-17-(Acetyloxy)-6-chloro-1,2-dihydro-3′H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione
• 1,2-alpha-Methylene-6-chloro-(sup 4,6)-pregnadiene-17-alpha-ol-3,20-dione 17-alpha-acetate
• 1,2-alpha-Methylene-6-chloro-delta(sup 6)-17-alpha-hydroxyprogesterone acetate
• 1,2-alpha-Methylene-6-chloro-pregna-4,6-diene-3,20-dione 17-alpha-acetate
• 1,2α-Methylene-6-chloro-17α-acetoxy-4,6-pregnadiene-3,20-dione
• 1,2α-Methylene-6-chloro-pregna-4,6-diene-3,20-dione 17α-acetate
• 1,2α-Methylene-6-chloro-Δ4,6-pregnadien-17α-ol-3,20-dione acetate
• 1,2α-Methylene-6-chloro-Δ^4,6-pregnadien-17α-ol-3,20-dione acetate
• 17-acetate de 6-chloro-1-β,2-β-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione
• 17-acetato de 6-cloro-1-β,2-β-dihidro-17-hidroxi-3'H-ciclopropa[1,2]pregna-1,4,6-trieno-3,20-diona
• 17-alpha-Acetoxy-6-chloro-1-alpha,2-alpha-methylenepregna-4,6-diene-3,20-dione
• 17α-Acetoxy-6-chloro-1α,2α-methylenepregna-4,6-diene-3,20-dione
• 3'H-Cyclopropa(1,2)pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-6-chloro-1,2-dihydro-, (1beta,2beta)-
• 3'H-Cyclopropa(1,2)pregna-1,4,6-triene-3,20-dione, 6-chloro-1-beta,2-beta-dihydro-17-hydroxy-, acetate
• 3'H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione
• 3'H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-6-chloro-1,2-dihydro-, (1β,2β)-
• 3'H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione, 6-chloro-1β,2β-dihydro-17-hydroxy-, acetate
• 3′H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione
• 3′H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-6-chloro-1,2-dihydro-, (1β,2β)-
• 3′H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione, 6-chloro-1β,2β-dihydro-17-hydroxy-, acetate
• 6-Chlor-1-β,2-β-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-trien-3,20-dion-17-acetat
• 6-Chlor-delta(sup 6)-1,2-alpha-methylen-17-alpha-hydroxyprogesteronacetat
• 6-Chlor-delta(sup 6)-1,2-alpha-methylen-17-alpha-hydroxyprogesteronacetat [German]
• 6-Chloro-1,2-alpha-methylene-17-alpha-hydroxy-delta(sup 6)-progesterone acetate
• 6-Chloro-1,2-alpha-methylene-6-dehydro-17-alpha-hydroxyprogesterone acetate
• 6-Chloro-1,2α-methylene-17α-hydroxy-Δ6-progesterone acetate
• 6-Chloro-1,2α-methylene-17α-hydroxy-Δ⁶-progesterone acetate
• 6-Chloro-1,2α-methylene-6-dehydro-17α-hydroxyprogesterone 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
• 6-Chloro-17-hydroxy-1-alpha,2-alpha-methylenepregna-4,6-diene-3,20-dione acetate
• 6-Chloro-17-hydroxy-1α,2α-methylenepregna-4,6-diene-3,20-dione acetate
• 6-Chloro-1beta,2beta-dihydro-17-hydroxy-3'H-cyclopropa(1,2)-pregna-1,4,6-triene-3,20-dione acetate
• 6-Chloro-delta(sup 6)-1,2-alpha-methylene-17-alpha-hydroxyprogesterone acetate
• 6-Chloro-delta-6-1,2alpha-methylene-17alpha-hydroxyprogesterone acetate
• 6-chloro-1-β,2-β-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione 17-acetate
• Androcur
• Androcur Depot
• CPA
• Ccris 4385
• Cyclopropa[1,2]cyclopenta[a]phenanthrene, 3′H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione deriv.
• Cyprostat
• Cyproteron acetate
• Cyproteron-R acetate
• Cyproterone 17-O-acetate
• Cyproterone 17alpha-acetate
• Cyproterone 17α-acetate
• Cyproviron
• Hsdb 3592
• Nsc 81430
• Pregna-4,6-diene-3,20-dione, 6-chloro-17-hydroxy-1-alpha,2-alpha-methylene-, acetate
• Pregna-4,6-diene-3,20-dione, 6-chloro-17-hydroxy-1α,2α-methylene-, acetate
• Sh 714
• Sh 80714

Cyproterone Acetate-13C2,d3 (Major)

Controlled Product

CAS: 427-51-0

Applications Labelled Cyproterone Acetate. The free alcohol is an anti-androgen; the acetate is both an anti-androgen and a progestogen. Combined with estrogen it is used in the treatment of acne.
References Moltz, L., et al.: Contraception, 21, 393 (1980), Hammerstein, J., et al.: J. Steroid Biochem., 29, 591 (1983)

Formula: C₂₂₁₃C₂H₂₆D₃ClO₄

Color and Shape: Neat

Molecular weight: 421.94

Ref: TR-C989102