Cyproterone acetate (CHEM003704)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2014-09-11 05:14:37 UTC
Update Date2026-03-26 21:34:31 UTC
Accession NumberCHEM003704
Identification
Common NameCyproterone acetate
ClassSmall Molecule
DescriptionAn anti-androgen that, in the form of its acetate (cyproterone acetate), also has progestational properties. It is used in the treatment of hypersexuality in males, as a palliative in prostatic carcinoma, and, in combination with estrogen, for the therapy of severe acne and hirsutism in females.
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Drug
  • Ester
  • Ether
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Acetic acid (8R,9S,10S,13S,14S,17R)-17-acetyl-6-(S)-chloro-10,13-dimethyl-3-(R)-oxo-1,2,3,8,9,10,11,12,13,14,15,16,17,20-tetradecahydro-cyclopropa[1,2]cyclopenta[a]phenanthren-17-yl esterChEBI
Apo-cyproteroneChEBI
Cyproterone 17-O-acetateChEBI
Acetate (8R,9S,10S,13S,14S,17R)-17-acetyl-6-(S)-chloro-10,13-dimethyl-3-(R)-oxo-1,2,3,8,9,10,11,12,13,14,15,16,17,20-tetradecahydro-cyclopropa[1,2]cyclopenta[a]phenanthren-17-yl esterGenerator
Cyproterone 17-O-acetic acidGenerator
Cyproterone acetic acidGenerator
AndrocurMeSH
Cyproterone acetate, (1 alpha,2 alpha)-isomerMeSH
Cyproterone acetate, (1 alpha,2 alpha,9 beta,10 alpha)-isomerMeSH
Cyproterone acetate, (17 alpha)-isomerMeSH
Chemical FormulaC24H29ClO4
Average Molecular Mass416.938 g/mol
Monoisotopic Mass416.175 g/mol
CAS Registry Number427-51-0
IUPAC Name(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-2,16-dimethyl-6-oxopentacyclo[9.7.0.0²,⁸.0³,⁵.0¹²,¹⁶]octadeca-7,9-dien-15-yl acetate
Traditional Namecyproterone acetate
SMILES[H][C@@]12C[C@]1([H])[C@@]1(C)C(=CC2=O)C(Cl)=C[C@@]2([H])[C@]3([H])CC[C@](OC(C)=O)(C(C)=O)[C@@]3(C)CC[C@]12[H]
InChI IdentifierInChI=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 KeyUWFYSQMTEOIJJG-FDTZYFLXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • Steroid ester
  • 3-oxosteroid
  • 6-halo-steroid
  • Halo-steroid
  • Oxosteroid
  • Cyclohexenone
  • Alpha-acyloxy ketone
  • Ketone
  • Carboxylic acid ester
  • Haloalkene
  • Chloroalkene
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Vinyl chloride
  • Vinyl halide
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point200-201°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP3.81ALOGPS
logP3.64ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)17.83ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.44 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity111.81 m³·mol⁻¹ChemAxon
Polarizability44.65 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-9211100001-d28e5fdc8591481f22f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01t9-3971000000-1dfca0904cf6f0055e70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009600000-b58e59a860b40f6fa16aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r1-1079100000-2b2076ee4e989b996df7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000m-6090000000-a52f873929348166d62aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-2007900000-9919c0052c65d1218b0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-2009100000-dd4f568fa03074230f01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7019000000-5bd7b03633e9ae6146acSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureCompletely absorbed following oral administration.
Mechanism of ToxicityThe direct antiandrogenic effect of cyproterone is blockage of the binding of dihydrotestosterone to the specific receptors in the prostatic carcinoma cell. In addition, cyproterone exerts a negative feed-back on the hypothalamo-pituitary axis, by inhibiting the secretion of luteinizing hormone resulting in diminished production of testicular testosterone.
MetabolismPrimarily hepatic. Cyproterone acetate is metabolized by the CYP3A4 enzyme, forming the active metabolite 15beta-hydroxycyproterone acetate, which retains its antiandrogen activity, but has reduced progestational activity. Route of Elimination: It is excreted approximately 60% in the bile and 33% through the kidneys. Half Life: Elimination Following oral or intramuscular administration, the plasma half-life is 38 and 96 hours, respectively.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the palliative treatment of patients with advanced prostatic carcinoma.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04839
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCyproterone_Acetate
Chemspider IDNot Available
ChEBI ID50743
PubChem Compound ID9880
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Aranya Manosroi, “Synthesis of cyproterone acetate.” U.S. Patent US20040024230, issued February 05, 2004.

MSDSNot Available
General ReferencesNot Available