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Identification
NameCyproterone acetate
Accession NumberDB04839
TypeSmall Molecule
GroupsApproved, Investigational
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. [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 mgOralBdh Inc.1998-10-082000-08-03Canada
CyproteroneTablet50 mgOralAa Pharma Inc2004-04-20Not applicableCanada
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 KeyUWFYSQMTEOIJJG-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]
Pharmacology
IndicationFor the palliative treatment of patients with advanced prostatic carcinoma.
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Androgen receptorProteinyes
antagonist
HumanP10275 details
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
Interactions
Drug Interactions
DrugInteractionDrug group
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
AcenocoumarolThe serum concentration of Acenocoumarol can be decreased when it is combined with Cyproterone acetate.Approved
AcetaminophenThe serum concentration of Acetaminophen can be decreased when it is combined with Cyproterone acetate.Approved
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Cyproterone acetate.Withdrawn
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Cyproterone acetate.Approved
AicarThe therapeutic efficacy of Aicar can be decreased when used in combination with Cyproterone acetate.Experimental
AlbendazoleThe serum concentration of Albendazole can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
AlmotriptanThe serum concentration of Almotriptan can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Cyproterone acetate.Approved
AlosetronThe serum concentration of Alosetron can be decreased when it is combined with Cyproterone acetate.Approved, Withdrawn
AminophenazoneThe serum concentration of Aminophenazone can be decreased when it is combined with Cyproterone acetate.Approved, Withdrawn
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with Cyproterone acetate.Approved
AmiodaroneThe serum concentration of Amiodarone can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
AmitriptylineThe serum concentration of Amitriptyline can be decreased when it is combined with Cyproterone acetate.Approved
AnagrelideThe serum concentration of Anagrelide can be decreased when it is combined with Cyproterone acetate.Approved
AnilineThe serum concentration of Aniline can be decreased when it is combined with Cyproterone acetate.Experimental
AntipyrineThe serum concentration of Antipyrine can be decreased when it is combined with Cyproterone acetate.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Cyproterone acetate.Investigational
ApixabanThe serum concentration of Apixaban can be decreased when it is combined with Cyproterone acetate.Approved
AprepitantThe serum concentration of Aprepitant can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Cyproterone acetate.Approved, Investigational
ASA404The serum concentration of ASA404 can be decreased when it is combined with Cyproterone acetate.Investigational
AsenapineThe serum concentration of Asenapine can be decreased when it is combined with Cyproterone acetate.Approved
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Cyproterone acetate.Approved
AV650The serum concentration of AV650 can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
AxitinibThe serum concentration of Axitinib can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
AzelastineThe serum concentration of Azelastine can be decreased when it is combined with Cyproterone acetate.Approved
BalaglitazoneThe therapeutic efficacy of Balaglitazone can be decreased when used in combination with Cyproterone acetate.Investigational
BendamustineThe serum concentration of Bendamustine can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
Benzyl alcoholThe serum concentration of Benzyl alcohol can be decreased when it is combined with Cyproterone acetate.Approved
BetaxololThe serum concentration of Betaxolol can be decreased when it is combined with Cyproterone acetate.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Cyproterone acetate.Approved, Investigational
BortezomibThe serum concentration of Bortezomib can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
BromazepamThe serum concentration of Bromazepam can be decreased when it is combined with Cyproterone acetate.Approved, Illicit
BrompheniramineThe serum concentration of Brompheniramine can be decreased when it is combined with Cyproterone acetate.Approved
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Cyproterone acetate.Withdrawn
BupivacaineThe serum concentration of Bupivacaine can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
BupropionThe serum concentration of Bupropion can be decreased when it is combined with Cyproterone acetate.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Cyproterone acetate.Approved
CaffeineThe serum concentration of Caffeine can be decreased when it is combined with Cyproterone acetate.Approved
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Cyproterone acetate.Approved
CapsaicinThe serum concentration of Capsaicin can be decreased when it is combined with Cyproterone acetate.Approved
CarbamazepineThe serum concentration of Carbamazepine can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
CarbinoxamineThe serum concentration of Carbinoxamine can be decreased when it is combined with Cyproterone acetate.Approved
CarmustineThe serum concentration of Carmustine can be decreased when it is combined with Cyproterone acetate.Approved
CarvedilolThe serum concentration of Carvedilol can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Cyproterone acetate.Experimental
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Cyproterone acetate.Withdrawn
ChlorpromazineThe serum concentration of Chlorpromazine can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Cyproterone acetate.Approved
ChlorzoxazoneThe serum concentration of Chlorzoxazone can be decreased when it is combined with Cyproterone acetate.Approved
Choline C 11The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Cyproterone acetate.Approved
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Cyproterone acetate.Experimental
CilostazolThe serum concentration of Cilostazol can be decreased when it is combined with Cyproterone acetate.Approved
CinacalcetThe serum concentration of Cinacalcet can be decreased when it is combined with Cyproterone acetate.Approved
CinnarizineThe serum concentration of Cinnarizine can be decreased when it is combined with Cyproterone acetate.Approved
CisaprideThe serum concentration of Cisapride can be decreased when it is combined with Cyproterone acetate.Approved, Investigational, Withdrawn
CitalopramThe serum concentration of Citalopram can be decreased when it is combined with Cyproterone acetate.Approved
ClenbuterolThe serum concentration of Clenbuterol can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
ClevidipineThe serum concentration of Clevidipine can be decreased when it is combined with Cyproterone acetate.Approved
ClomipramineThe serum concentration of Clomipramine can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
ClonidineThe serum concentration of Clonidine can be decreased when it is combined with Cyproterone acetate.Approved
ClopidogrelThe serum concentration of Clopidogrel can be decreased when it is combined with Cyproterone acetate.Approved, Nutraceutical
ClozapineThe serum concentration of Clozapine can be decreased when it is combined with Cyproterone acetate.Approved
Coenzyme Q10The serum concentration of Coenzyme Q10 can be increased when it is combined with Cyproterone acetate.Experimental
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be decreased when it is combined with Cyproterone acetate.Approved
CyclobenzaprineThe serum concentration of Cyclobenzaprine can be decreased when it is combined with Cyproterone acetate.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Cyproterone acetate.Approved, Investigational
DacarbazineThe serum concentration of Dacarbazine can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DalfampridineThe serum concentration of Dalfampridine can be decreased when it is combined with Cyproterone acetate.Approved
DapagliflozinThe serum concentration of Dapagliflozin can be decreased when it is combined with Cyproterone acetate.Approved
DapsoneThe serum concentration of Dapsone can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DasatinibThe serum concentration of Dasatinib can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Cyproterone acetate.Approved
DeoxyspergualinThe therapeutic efficacy of Deoxyspergualin can be decreased when used in combination with Cyproterone acetate.Investigational
DesipramineThe serum concentration of Desipramine can be decreased when it is combined with Cyproterone acetate.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Cyproterone acetate.Approved
DexfenfluramineThe serum concentration of Dexfenfluramine can be decreased when it is combined with Cyproterone acetate.Approved, Illicit, Withdrawn
DexmedetomidineThe serum concentration of Dexmedetomidine can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
DextromethorphanThe serum concentration of Dextromethorphan can be decreased when it is combined with Cyproterone acetate.Approved
DiazepamThe serum concentration of Diazepam can be decreased when it is combined with Cyproterone acetate.Approved, Illicit, Vet Approved
DiclofenacThe serum concentration of Diclofenac can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Cyproterone acetate.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Cyproterone acetate.Approved
DinoprostoneThe serum concentration of Dinoprostone can be decreased when it is combined with Cyproterone acetate.Approved
DiphenhydramineThe serum concentration of Diphenhydramine can be decreased when it is combined with Cyproterone acetate.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Cyproterone acetate.Approved, Investigational
DomperidoneThe serum concentration of Domperidone can be decreased when it is combined with Cyproterone acetate.Approved, Investigational, Vet Approved
DoxepinThe serum concentration of Doxepin can be decreased when it is combined with Cyproterone acetate.Approved
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Cyproterone acetate.Approved
DuloxetineThe serum concentration of Duloxetine can be decreased when it is combined with Cyproterone acetate.Approved
EltrombopagThe serum concentration of Eltrombopag can be decreased when it is combined with Cyproterone acetate.Approved
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Cyproterone acetate.Approved
EnfluraneThe serum concentration of Enflurane can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
EnfuvirtideThe serum concentration of Enfuvirtide can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
ErgotamineThe serum concentration of Ergotamine can be decreased when it is combined with Cyproterone acetate.Approved
ErlotinibThe serum concentration of Erlotinib can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Cyproterone acetate.Approved, Investigational, Vet Approved
EstroneThe serum concentration of Estrone can be decreased when it is combined with Cyproterone acetate.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be decreased when it is combined with Cyproterone acetate.Approved
EthanolThe therapeutic efficacy of Cyproterone acetate can be decreased when used in combination with Ethanol.Approved
Ethanolamine OleateThe serum concentration of Ethanolamine Oleate can be decreased when it is combined with Cyproterone acetate.Approved
EthosuximideThe serum concentration of Ethosuximide can be decreased when it is combined with Cyproterone acetate.Approved
EtoposideThe serum concentration of Etoposide can be decreased when it is combined with Cyproterone acetate.Approved
EtoricoxibThe serum concentration of Etoricoxib can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
ExenatideThe therapeutic efficacy of Exenatide can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
FelbamateThe serum concentration of Felbamate can be decreased when it is combined with Cyproterone acetate.Approved
FingolimodThe serum concentration of Fingolimod can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
FlunarizineThe serum concentration of Flunarizine can be decreased when it is combined with Cyproterone acetate.Approved
FlunitrazepamThe serum concentration of Flunitrazepam can be decreased when it is combined with Cyproterone acetate.Approved, Illicit
FluorouracilThe serum concentration of Fluorouracil can be decreased when it is combined with Cyproterone acetate.Approved
FluoxetineThe serum concentration of Fluoxetine can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
FlutamideThe serum concentration of Flutamide can be decreased when it is combined with Cyproterone acetate.Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Cyproterone acetate.Approved
FluvoxamineThe serum concentration of Fluvoxamine can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
Folic AcidThe serum concentration of Folic Acid can be decreased when it is combined with Cyproterone acetate.Approved, Nutraceutical, Vet Approved
FrovatriptanThe serum concentration of Frovatriptan can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
GenisteinThe serum concentration of Genistein can be decreased when it is combined with Cyproterone acetate.Investigational
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Cyproterone acetate.Withdrawn
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Cyproterone acetate.Approved
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Cyproterone acetate.Approved
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Cyproterone acetate.Approved
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Cyproterone acetate.Approved
GlucosamineThe serum concentration of Glucosamine can be decreased when it is combined with Cyproterone acetate.Approved
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Cyproterone acetate.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be decreased when it is combined with Cyproterone acetate.Withdrawn
GuanabenzThe serum concentration of Guanabenz can be decreased when it is combined with Cyproterone acetate.Approved
GusperimusThe therapeutic efficacy of Gusperimus can be decreased when used in combination with Cyproterone acetate.Investigational
HaloperidolThe serum concentration of Haloperidol can be decreased when it is combined with Cyproterone acetate.Approved
HalothaneThe serum concentration of Halothane can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
HesperetinThe serum concentration of Hesperetin can be decreased when it is combined with Cyproterone acetate.Approved
HexobarbitalThe serum concentration of Hexobarbital can be decreased when it is combined with Cyproterone acetate.Approved
IloperidoneThe serum concentration of Iloperidone can be decreased when it is combined with Cyproterone acetate.Approved
ImatinibThe serum concentration of Imatinib can be decreased when it is combined with Cyproterone acetate.Approved
ImipramineThe serum concentration of Imipramine can be decreased when it is combined with Cyproterone acetate.Approved
ImiquimodThe serum concentration of Imiquimod can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Cyproterone acetate.Approved
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Cyproterone acetate.Approved
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Cyproterone acetate.Approved
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Cyproterone acetate.Approved
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Cyproterone acetate.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Cyproterone acetate.Approved
IsofluraneThe serum concentration of Isoflurane can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
IsoniazidThe serum concentration of Isoniazid can be decreased when it is combined with Cyproterone acetate.Approved
IxazomibThe serum concentration of Ixazomib can be decreased when it is combined with Cyproterone acetate.Approved
LeflunomideThe serum concentration of Leflunomide can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
LevobupivacaineThe serum concentration of Levobupivacaine can be decreased when it is combined with Cyproterone acetate.Approved
LidocaineThe serum concentration of Lidocaine can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Cyproterone acetate.Approved
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Cyproterone acetate.Approved
LomefloxacinThe serum concentration of Lomefloxacin can be decreased when it is combined with Cyproterone acetate.Approved
LorcaserinThe serum concentration of Lorcaserin can be decreased when it is combined with Cyproterone acetate.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Cyproterone acetate.Approved, Investigational
LumiracoxibThe serum concentration of Lumiracoxib can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
MalathionThe serum concentration of Malathion can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
MaprotilineThe serum concentration of Maprotiline can be decreased when it is combined with Cyproterone acetate.Approved
MelatoninThe serum concentration of Melatonin can be decreased when it is combined with Cyproterone acetate.Approved, Nutraceutical, Vet Approved
MenadioneThe serum concentration of Menadione can be decreased when it is combined with Cyproterone acetate.Approved, Nutraceutical
MephenytoinThe serum concentration of Mephenytoin can be decreased when it is combined with Cyproterone acetate.Investigational, Withdrawn
MeprobamateThe serum concentration of Meprobamate can be decreased when it is combined with Cyproterone acetate.Approved, Illicit
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Cyproterone acetate.Approved
MethadoneThe serum concentration of Methadone can be decreased when it is combined with Cyproterone acetate.Approved
MethoxyfluraneThe serum concentration of Methoxyflurane can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Cyproterone acetate.Experimental
MexiletineThe serum concentration of Mexiletine can be decreased when it is combined with Cyproterone acetate.Approved
MianserinThe serum concentration of Mianserin can be decreased when it is combined with Cyproterone acetate.Approved
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Cyproterone acetate.Approved
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Cyproterone acetate.Approved
MirtazapineThe serum concentration of Mirtazapine can be decreased when it is combined with Cyproterone acetate.Approved
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
MitoxantroneThe serum concentration of Mitoxantrone can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
muraglitazarThe serum concentration of muraglitazar can be decreased when it is combined with Cyproterone acetate.Investigational
NabumetoneThe serum concentration of Nabumetone can be decreased when it is combined with Cyproterone acetate.Approved
NaproxenThe serum concentration of Naproxen can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
NicardipineThe serum concentration of Nicardipine can be decreased when it is combined with Cyproterone acetate.Approved
NicotineThe serum concentration of Nicotine can be decreased when it is combined with Cyproterone acetate.Approved
NifedipineThe serum concentration of Nifedipine can be decreased when it is combined with Cyproterone acetate.Approved
NilvadipineThe serum concentration of Nilvadipine can be decreased when it is combined with Cyproterone acetate.Approved
Nitric OxideThe serum concentration of Nitric Oxide can be decreased when it is combined with Cyproterone acetate.Approved
NortriptylineThe serum concentration of Nortriptyline can be decreased when it is combined with Cyproterone acetate.Approved
OlanzapineThe serum concentration of Olanzapine can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
OmeprazoleThe serum concentration of Omeprazole can be decreased when it is combined with Cyproterone acetate.Approved, Investigational, Vet Approved
OndansetronThe serum concentration of Ondansetron can be decreased when it is combined with Cyproterone acetate.Approved
OuabainOuabain may decrease the cardiotoxic activities of Cyproterone acetate.Approved
OxaliplatinThe serum concentration of Oxaliplatin can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
OxtriphyllineThe serum concentration of Oxtriphylline can be decreased when it is combined with Cyproterone acetate.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Cyproterone acetate.Approved, Vet Approved
PalonosetronThe serum concentration of Palonosetron can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
PantoprazoleThe serum concentration of Pantoprazole can be decreased when it is combined with Cyproterone acetate.Approved
ParamethadioneThe serum concentration of Paramethadione can be decreased when it is combined with Cyproterone acetate.Approved
PazopanibThe serum concentration of Pazopanib can be decreased when it is combined with Cyproterone acetate.Approved
PentamidineThe serum concentration of Pentamidine can be decreased when it is combined with Cyproterone acetate.Approved
PentoxifyllineThe serum concentration of Pentoxifylline can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
PerphenazineThe serum concentration of Perphenazine can be decreased when it is combined with Cyproterone acetate.Approved
PhenacetinThe serum concentration of Phenacetin can be decreased when it is combined with Cyproterone acetate.Withdrawn
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Cyproterone acetate.Approved, Withdrawn
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with Cyproterone acetate.Approved
PilocarpineThe serum concentration of Pilocarpine can be decreased when it is combined with Cyproterone acetate.Approved
PimozideThe serum concentration of Pimozide can be decreased when it is combined with Cyproterone acetate.Approved
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
PipotiazineThe serum concentration of Pipotiazine can be decreased when it is combined with Cyproterone acetate.Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Cyproterone acetate.Approved
PomalidomideThe serum concentration of Pomalidomide can be decreased when it is combined with Cyproterone acetate.Approved
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Cyproterone acetate.Approved
PraziquantelThe serum concentration of Praziquantel can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
PrimaquineThe serum concentration of Primaquine can be decreased when it is combined with Cyproterone acetate.Approved
ProgesteroneThe serum concentration of Progesterone can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
ProguanilThe serum concentration of Proguanil can be decreased when it is combined with Cyproterone acetate.Approved
PromazineThe serum concentration of Promazine can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
PropafenoneThe serum concentration of Propafenone can be decreased when it is combined with Cyproterone acetate.Approved
PropofolThe serum concentration of Propofol can be decreased when it is combined with Cyproterone acetate.Approved, Investigational, Vet Approved
PropranololThe serum concentration of Propranolol can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
PyrazinamideThe serum concentration of Pyrazinamide can be decreased when it is combined with Cyproterone acetate.Approved
QuinidineThe serum concentration of Quinidine can be decreased when it is combined with Cyproterone acetate.Approved
QuinineThe serum concentration of Quinine can be decreased when it is combined with Cyproterone acetate.Approved
RamelteonThe serum concentration of Ramelteon can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
RanitidineThe serum concentration of Ranitidine can be decreased when it is combined with Cyproterone acetate.Approved
RasagilineThe serum concentration of Rasagiline can be decreased when it is combined with Cyproterone acetate.Approved
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
ResveratrolThe serum concentration of Resveratrol can be decreased when it is combined with Cyproterone acetate.Experimental, Investigational
RifabutinThe serum concentration of Rifabutin can be decreased when it is combined with Cyproterone acetate.Approved
RiluzoleThe serum concentration of Riluzole can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
RitonavirThe serum concentration of Ritonavir can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
RizatriptanThe serum concentration of Rizatriptan can be decreased when it is combined with Cyproterone acetate.Approved
RofecoxibThe serum concentration of Rofecoxib can be decreased when it is combined with Cyproterone acetate.Investigational, Withdrawn
RopiniroleThe serum concentration of Ropinirole can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
RopivacaineThe serum concentration of Ropivacaine can be decreased when it is combined with Cyproterone acetate.Approved
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Cyproterone acetate.Approved
RotigotineThe serum concentration of Rotigotine can be decreased when it is combined with Cyproterone acetate.Approved
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Cyproterone acetate.Approved
SelegilineThe serum concentration of Selegiline can be decreased when it is combined with Cyproterone acetate.Approved, Investigational, Vet Approved
SertralineThe serum concentration of Sertraline can be decreased when it is combined with Cyproterone acetate.Approved
SevofluraneThe serum concentration of Sevoflurane can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
SildenafilThe serum concentration of Sildenafil can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Cyproterone acetate.Approved
SitagliptinThe therapeutic efficacy of Sitagliptin can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
SulfadiazineThe serum concentration of Sulfadiazine can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
TacrineThe serum concentration of Tacrine can be decreased when it is combined with Cyproterone acetate.Withdrawn
TamoxifenThe serum concentration of Tamoxifen can be decreased when it is combined with Cyproterone acetate.Approved
TelithromycinThe serum concentration of Telithromycin can be decreased when it is combined with Cyproterone acetate.Approved
TemafloxacinThe serum concentration of Temafloxacin can be decreased when it is combined with Cyproterone acetate.Withdrawn
TerbinafineThe serum concentration of Terbinafine can be decreased when it is combined with Cyproterone acetate.Approved, Investigational, Vet Approved
ThalidomideThe serum concentration of Thalidomide can be decreased when it is combined with Cyproterone acetate.Approved, Investigational, Withdrawn
TheobromineThe serum concentration of Theobromine can be decreased when it is combined with Cyproterone acetate.Approved
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with Cyproterone acetate.Approved
ThiabendazoleThe serum concentration of Thiabendazole can be decreased when it is combined with Cyproterone acetate.Approved, Vet Approved
ThiazolidinedioneThe therapeutic efficacy of Thiazolidinedione can be decreased when used in combination with Cyproterone acetate.Investigational
ThioridazineThe serum concentration of Thioridazine can be decreased when it is combined with Cyproterone acetate.Approved
ThiothixeneThe serum concentration of Thiothixene can be decreased when it is combined with Cyproterone acetate.Approved
TirapazamineThe serum concentration of Tirapazamine can be decreased when it is combined with Cyproterone acetate.Investigational
TizanidineThe serum concentration of Tizanidine can be decreased when it is combined with Cyproterone acetate.Approved
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Cyproterone acetate.Approved
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Cyproterone acetate.Approved
ToremifeneThe serum concentration of Toremifene can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
TrabectedinThe serum concentration of Trabectedin can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Cyproterone acetate.Approved, Investigational
TriamtereneThe serum concentration of Triamterene can be decreased when it is combined with Cyproterone acetate.Approved
TrifluoperazineThe serum concentration of Trifluoperazine can be decreased when it is combined with Cyproterone acetate.Approved
TrimethadioneThe serum concentration of Trimethadione can be decreased when it is combined with Cyproterone acetate.Approved
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Cyproterone acetate.Withdrawn
UlipristalThe serum concentration of Ulipristal can be decreased when it is combined with Cyproterone acetate.Approved
VerapamilThe serum concentration of Verapamil can be decreased when it is combined with Cyproterone acetate.Approved
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
WarfarinThe serum concentration of Warfarin can be decreased when it is combined with Cyproterone acetate.Approved
ZileutonThe serum concentration of Zileuton can be decreased when it is combined with Cyproterone acetate.Approved, Investigational, Withdrawn
ZiprasidoneThe serum concentration of Ziprasidone can be decreased when it is combined with Cyproterone acetate.Approved
ZolmitriptanThe serum concentration of Zolmitriptan can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
ZolpidemThe serum concentration of Zolpidem can be decreased when it is combined with Cyproterone acetate.Approved
ZopicloneThe serum concentration of Zopiclone can be decreased when it is combined with Cyproterone acetate.Approved
Food Interactions
  • Avoid alcohol.
  • Take after a meal.
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
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
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

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