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Substance Name: Cyproterone acetate [USAN:JAN]
RN: 427-51-0
UNII: 4KM2BN5JHF
InChIKey: UWFYSQMTEOIJJG-FDTZYFLXSA-N

Note

  • An agent with anti-androgen and progestational properties. It shows competitive binding with dihydrotestosterone at androgen receptor sites.

Molecular Formula

  • C24-H29-Cl-O4

Molecular Weight

  • 416.9421
 

Classification Codes

  • Androgen Antagonists
  • Anti-Androgen
  • Antineoplastic Agents
  • Contraceptive Agents
  • Contraceptive Agents, Male
  • Drug / Therapeutic Agent
  • Hormone Antagonists
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Human Data
  • Mutation Data
  • Reproductive Control Agents
  • Reproductive Effect
  • Tumor Data
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Names and Synonyms

Name of Substance

  • Cyproterone acetate
  • Cyproterone acetate [USAN:JAN]

MeSH Heading

  • Cyproterone acetate

Synonyms

  • 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
  • 17-alpha-Acetoxy-6-chloro-1-alpha,2-alpha-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)-
  • 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-17-hydroxy-1-alpha,2-alpha-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
  • Androcur
  • CCRIS 4385
  • Cyprostat
  • Cyproteron acetate
  • Cyproteron-R acetate
  • Cyproterone 17-O-acetate
  • Cyproterone 17alpha-acetate
  • Cyproterone acetate
  • EINECS 207-048-3
  • HSDB 3592
  • NSC 81430
  • NSC-81430
  • Pregna-4,6-diene-3,20-dione, 6-chloro-17-hydroxy-1-alpha,2-alpha-methylene-, acetate
  • SH 714
  • SH 80714
  • UNII-4KM2BN5JHF

Systematic Names

  • 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
  • 6-Chloro-1-beta,2-beta-dihydro-17-hydroxy-3'H-cyclopropa(1,2)pregna-1,4,6-triene-3,20-dione 17-acetate
  • Cyproterone acetate

Superlist Name

  • Cyproterone acetate

Registry Numbers

CAS Registry Number

  • 427-51-0

FDA UNII

  • 4KM2BN5JHF

System Generated Number

  • 0000427510

Structure Descriptors

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

InChIKey

UWFYSQMTEOIJJG-FDTZYFLXSA-N

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man LDLo oral 171mg/kg/17W- (171mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LIVER: LIVER FUNCTION TESTS IMPAIRED		 Israel Journal of Medical Sciences. Vol. 30, Pg. 238, 1994.
man TDLo oral 514mg/kg/7W-I (514mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"		 Australian and New Zealand Journal of Medicine. Vol. 26, Pg. 724, 1996.
mouse LD50 intraperitoneal 3300mg/kg (3300mg/kg)   Drugs in Japan Vol. 6, Pg. APP-4, 1982.
mouse LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. APP-4, 1982.
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. APP-4, 1982.
rat LD50 intraperitoneal 565mg/kg (565mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 349, 1982.
rat LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. APP-4, 1982.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. APP-4, 1982.