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Identification
NameCyproterone acetate
Accession NumberDB04839
TypeSmall Molecule
GroupsApproved, Investigational
Description

An 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. [Pubchem]

Structure
Thumb
Synonyms
Cyproterone 17-O-acetate
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alti-cpatablet50 mgoralAltimed Pharma Inc.1997-09-222005-05-27Canada
Androcurtablet50 mgoralBayer Inc1987-12-31Not applicableCanada
Androcur Depotsolution100 mgintramuscularBayer Inc1990-12-31Not applicableCanada
Cyproteronetablet50 mgoralAa Pharma Inc2004-04-20Not applicableCanada
Cyproteronetablet50 mgoralBdh Inc.1998-10-082000-08-03Canada
Med-cyproteronetablet50 mgoralGeneric Medical Partners Inc2012-10-02Not applicableCanada
Mylan-cyproteronetablet50 mgoralMylan Pharmaceuticals Ulc1997-09-192011-03-04Canada
Novo-cyproteronetablet50 mgoralNovopharm Limited1997-09-172015-10-26Canada
Riva-cyproteronetablet50 mgoralLaboratoire Riva Inc2012-11-28Not applicableCanada
Riva-cyproterone 50 mgtablet50 mgoralLaboratoire Riva Inc2000-05-122003-07-28Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CyprostatBayer
Brand mixtures
NameLabellerIngredients
Cléo -35Aspri Pharma Canada Inc
Cyestra-35Paladin Labs Inc
Diane-35Bayer Inc
Novo-cyproterone/ethinyl EstradiolTeva Canada Limited
Ran-cyproterone/ethinyl EstradiolRanbaxy Pharmaceuticals Canada Inc.
SaltsNot Available
Categories
UNII4KM2BN5JHF
CAS number427-51-0
WeightAverage: 416.938
Monoisotopic: 416.175437123
Chemical FormulaC24H29ClO4
InChI KeyInChIKey=UWFYSQMTEOIJJG-HEULQOMWNA-N
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-/s2
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
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]
Taxonomy
DescriptionThis compound 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
  • Steroid ester
  • 20-oxosteroid
  • Oxosteroid
  • Halo-steroid
  • 6-halo-steroid
  • 3-oxosteroid
  • Alpha-acyloxy ketone
  • Acetate salt
  • Ketone
  • Carboxylic acid ester
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the palliative treatment of patients with advanced prostatic carcinoma.
PharmacodynamicsCyproterone is an antiandrogen. It suppresses the actions of testosterone (and its metabolite dihydrotestosterone) on tissues. It acts by blocking androgen receptors which prevents androgens from binding to them and suppresses luteinizing hormone (which in turn reduces testosterone levels).
Mechanism of actionThe 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.
Related Articles
AbsorptionCompletely absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Primarily 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.

SubstrateEnzymesProduct
Cyproterone acetate
Not Available
15beta-hydroxycyproterone acetateDetails
Route of eliminationIt is excreted approximately 60% in the bile and 33% through the kidneys.
Half lifeElimination Following oral or intramuscular administration, the plasma half-life is 38 and 96 hours, respectively.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9673
Caco-2 permeable+0.7033
P-glycoprotein substrateSubstrate0.7292
P-glycoprotein inhibitor IInhibitor0.5265
P-glycoprotein inhibitor IINon-inhibitor0.9016
Renal organic cation transporterNon-inhibitor0.8036
CYP450 2C9 substrateNon-substrate0.8
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7834
CYP450 1A2 substrateNon-inhibitor0.8944
CYP450 2C9 inhibitorNon-inhibitor0.7229
CYP450 2D6 inhibitorNon-inhibitor0.8951
CYP450 2C19 inhibitorNon-inhibitor0.737
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8919
Ames testNon AMES toxic0.7067
CarcinogenicityNon-carcinogens0.926
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8261 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9704
hERG inhibition (predictor II)Non-inhibitor0.6939
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Solutionintramuscular100 mg
Tabletoral50 mg
Tabletoral
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point200-201Wiechert, R.; U S . Patent 3,234,093; February 8, 1966; assigned to Schering AG, Germany.
Predicted Properties
PropertyValueSource
Water Solubility0.00152 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity111.81 m3·mol-1ChemAxon
Polarizability44.65 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR13C NMR SpectrumNot Available
References
Synthesis Reference

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

US20040024230
General References
  1. Giorgi EP, Shirley IM, Grant JK, Stewart JC: Androgen dynamics in vitro in the human prostate gland. Effect of cyproterone and cyproterone acetate. Biochem J. 1973 Mar;132(3):465-74. [PubMed:4125095 ]
  2. Pham-Huu-Trung MT, de Smitter N, Bogyo A, Girard F: Effects of cyproterone acetate on adrenal steroidogenesis in vitro. Horm Res. 1984;20(2):108-15. [PubMed:6237971 ]
  3. Stadtler FA, Langner V: The effect of cyproterone and gonadotrophins on the adrenal gland of juvenile and adult rats. A morphological and morphometrical study. Pathol Res Pract. 1985 Mar;179(4-5):493-8. [PubMed:4001026 ]
  4. Honer C, Nam K, Fink C, Marshall P, Ksander G, Chatelain RE, Cornell W, Steele R, Schweitzer R, Schumacher C: Glucocorticoid receptor antagonism by cyproterone acetate and RU486. Mol Pharmacol. 2003 May;63(5):1012-20. [PubMed:12695529 ]
  5. Holdaway IM, Croxson MS, Evans MC, France J, Sheehan A, Wilson T, Ibbertson HK: Effect of cyproterone acetate on glucocorticoid secretion in patients treated for hirsutism. Acta Endocrinol (Copenh). 1983 Oct;104(2):222-6. [PubMed:6227191 ]
External Links
ATC CodesG03HB01G03HA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Cyproterone acetate.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Cyproterone acetate.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Cyproterone acetate.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Cyproterone acetate.
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with Cyproterone acetate.
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Cyproterone acetate.
AprepitantThe serum concentration of Cyproterone acetate can be increased when it is combined with Aprepitant.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Cyproterone acetate.
AsenapineThe serum concentration of Asenapine can be decreased when it is combined with Cyproterone acetate.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Cyproterone acetate.
BetaxololThe serum concentration of Betaxolol can be decreased when it is combined with Cyproterone acetate.
BexaroteneThe serum concentration of Cyproterone acetate can be decreased when it is combined with Bexarotene.
BortezomibThe serum concentration of Bortezomib can be decreased when it is combined with Cyproterone acetate.
BosentanThe serum concentration of Cyproterone acetate can be decreased when it is combined with Bosentan.
C1 Esterase Inhibitor (Human)Cyproterone acetate may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Cyproterone acetate.
CapromabCyproterone acetate may decrease effectiveness of Capromab as a diagnostic agent.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Cyproterone acetate.
Choline C 11The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Cyproterone acetate.
Citric AcidThe therapeutic efficacy of Citric Acid can be decreased when used in combination with Cyproterone acetate.
ClomipramineThe serum concentration of Clomipramine can be decreased when it is combined with Cyproterone acetate.
ClozapineThe serum concentration of Clozapine can be decreased when it is combined with Cyproterone acetate.
ConivaptanThe serum concentration of Cyproterone acetate can be increased when it is combined with Conivaptan.
DabrafenibThe serum concentration of Cyproterone acetate can be decreased when it is combined with Dabrafenib.
DacarbazineThe serum concentration of Dacarbazine can be decreased when it is combined with Cyproterone acetate.
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Cyproterone acetate.
DasatinibThe serum concentration of Cyproterone acetate can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Cyproterone acetate can be decreased when it is combined with Deferasirox.
DicoumarolThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Cyproterone acetate.
DrospirenoneThe serum concentration of Drospirenone can be decreased when it is combined with Cyproterone acetate.
DuloxetineThe serum concentration of Duloxetine can be decreased when it is combined with Cyproterone acetate.
Edetic AcidThe therapeutic efficacy of Edetic Acid can be decreased when used in combination with Cyproterone acetate.
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Cyproterone acetate.
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Cyproterone acetate.
Estrone sulfateThe serum concentration of Estropipate can be decreased when it is combined with Cyproterone acetate.
EthanolThe therapeutic efficacy of Cyproterone acetate can be decreased when used in combination with Ethanol.
Ethyl biscoumacetateThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Cyproterone acetate.
FluconazoleThe metabolism of Cyproterone acetate can be decreased when combined with Fluconazole.
FlutamideThe serum concentration of Flutamide can be decreased when it is combined with Cyproterone acetate.
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Cyproterone acetate.
FluvoxamineThe serum concentration of Fluvoxamine can be decreased when it is combined with Cyproterone acetate.
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Cyproterone acetate.
FosaprepitantThe serum concentration of Cyproterone acetate can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Cyproterone acetate can be increased when it is combined with Fusidic Acid.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Cyproterone acetate.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Cyproterone acetate.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Cyproterone acetate.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Cyproterone acetate.
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Cyproterone acetate.
IdelalisibThe serum concentration of Cyproterone acetate can be increased when it is combined with Idelalisib.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Cyproterone acetate.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Cyproterone acetate.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Cyproterone acetate.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Cyproterone acetate.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Cyproterone acetate.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Cyproterone acetate.
IsoniazidThe serum concentration of Isoniazid can be decreased when it is combined with Cyproterone acetate.
IvacaftorThe serum concentration of Cyproterone acetate can be increased when it is combined with Ivacaftor.
LidocaineThe serum concentration of Lidocaine can be decreased when it is combined with Cyproterone acetate.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Cyproterone acetate.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Cyproterone acetate.
LuliconazoleThe serum concentration of Cyproterone acetate can be increased when it is combined with Luliconazole.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Cyproterone acetate.
MexiletineThe serum concentration of Mexiletine can be decreased when it is combined with Cyproterone acetate.
MifepristoneThe serum concentration of Cyproterone acetate can be increased when it is combined with Mifepristone.
MirtazapineThe serum concentration of Mirtazapine can be decreased when it is combined with Cyproterone acetate.
MitotaneThe serum concentration of Cyproterone acetate can be decreased when it is combined with Mitotane.
NelfinavirThe metabolism of Cyproterone acetate can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Cyproterone acetate can be increased when it is combined with Netupitant.
NicotineThe serum concentration of Nicotine can be decreased when it is combined with Cyproterone acetate.
NorgestimateThe serum concentration of Norgestimate can be decreased when it is combined with Cyproterone acetate.
OlanzapineThe serum concentration of Olanzapine can be decreased when it is combined with Cyproterone acetate.
PalbociclibThe serum concentration of Cyproterone acetate can be increased when it is combined with Palbociclib.
PhenindioneThe therapeutic efficacy of Phenindione can be decreased when used in combination with Cyproterone acetate.
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Cyproterone acetate.
PhenytoinThe metabolism of Cyproterone acetate can be increased when combined with Phenytoin.
PimozideThe serum concentration of Pimozide can be decreased when it is combined with Cyproterone acetate.
PomalidomideThe serum concentration of Pomalidomide can be decreased when it is combined with Cyproterone acetate.
PropranololThe serum concentration of Propranolol can be decreased when it is combined with Cyproterone acetate.
RasagilineThe serum concentration of Rasagiline can be decreased when it is combined with Cyproterone acetate.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Cyproterone acetate.
RiluzoleThe serum concentration of Riluzole can be decreased when it is combined with Cyproterone acetate.
RopiniroleThe serum concentration of Ropinirole can be decreased when it is combined with Cyproterone acetate.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Cyproterone acetate.
SiltuximabThe serum concentration of Cyproterone acetate can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Cyproterone acetate can be increased when it is combined with Simeprevir.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Cyproterone acetate.
St. John's WortThe serum concentration of Cyproterone acetate can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Cyproterone acetate can be increased when it is combined with Stiripentol.
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Cyproterone acetate.
TasimelteonThe serum concentration of Tasimelteon can be decreased when it is combined with Cyproterone acetate.
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with Cyproterone acetate.
ThiothixeneThe serum concentration of Thiothixene can be decreased when it is combined with Cyproterone acetate.
TocilizumabThe serum concentration of Cyproterone acetate can be decreased when it is combined with Tocilizumab.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Cyproterone acetate.
TreprostinilThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Cyproterone acetate.
TrifluoperazineThe serum concentration of Trifluoperazine can be decreased when it is combined with Cyproterone acetate.
UlipristalThe therapeutic efficacy of Cyproterone acetate can be decreased when used in combination with Ulipristal.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Cyproterone acetate.
WarfarinThe therapeutic efficacy of Warfarin can be decreased when used in combination with Cyproterone acetate.
Food Interactions
  • Avoid alcohol.
  • Take after a meal.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Agoulnik IU, Weigel NL: Coactivator selective regulation of androgen receptor activity. Steroids. 2009 Aug;74(8):669-74. doi: 10.1016/j.steroids.2009.02.007. Epub 2009 Mar 9. [PubMed:19463689 ]
  4. Cabeza M, Flores M, Bratoeff E, de la Pena A, Mendez E, Ceballos G: Intracellular Ca2+ stimulates the binding to androgen receptors in platelets. Steroids. 2004 Oct-Nov;69(11-12):767-72. [PubMed:15579329 ]
  5. Sonneveld E, Jansen HJ, Riteco JA, Brouwer A, van der Burg B: Development of androgen- and estrogen-responsive bioassays, members of a panel of human cell line-based highly selective steroid-responsive bioassays. Toxicol Sci. 2005 Jan;83(1):136-48. Epub 2004 Oct 13. [PubMed:15483189 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
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Drug created on September 26, 2007 09:23 / Updated on August 17, 2016 12:24