abiraterone acetate Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antiandrogens 4176 154229-18-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • abiraterone acetate
  • zytiga
  • CB-7630
  • CB7630
Abiraterone acetate is converted in vivo to abiraterone, an androgen biosynthesis inhibitor, that inhibits 17 alpha-hydroxylase/C17,20-lyase (CYP17). This enzyme is expressed in testicular, adrenal, and prostatic tumor tissues and is required for androgen biosynthesis. CYP17 catalyzes two sequential reactions: 1) the conversion of pregnenolone and progesterone to their 17alpha-hydroxy derivatives by 17alpha-hydroxylase activity and 2) the subsequent formation of dehydroepiandrosterone (DHEA) and androstenedione, respectively, by C17,20 lyase activity. DHEA and androstenedione are androgens and are precursors of testosterone. Inhibition of CYP17 by abiraterone can also result in increased mineralocorticoid production by the adrenals. Androgen sensitive prostatic carcinoma responds to treatment that decreases androgen levels. Androgen deprivation therapies, such as treatment with GnRH agonists or orchiectomy, decrease androgen production in the testes but do not affect androgen production by the adrenals or in the tumor. Abiraterone acetate decreased serum testosterone and other androgens in patients in the placebo-controlled clinical trial. It is not necessary to monitor the effect of abiraterone acetate on serum testosterone levels.
  • Molecular weight: 391.56
  • Formula: C26H33NO2
  • CLOGP: 6.11
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 0
  • TPSA: 39.19
  • ALOGS: -5.59
  • ROTB: 3

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1 g O

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
Sept. 5, 2011 EMA
April 28, 2011 FDA JANSSEN BIOTECH

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC L02BX03 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ENDOCRINE THERAPY
HORMONE ANTAGONISTS AND RELATED AGENTS
Other hormone antagonists and related agents
FDA MoA N0000182632 Cytochrome P450 17A1 Inhibitors
FDA EPC N0000182633 Cytochrome P450 17A1 Inhibitor
FDA MoA N0000182137 Cytochrome P450 2D6 Inhibitors
FDA MoA N0000187062 Cytochrome P450 2C8 Inhibitors
MeSH PA D000970 Antineoplastic Agents
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D006727 Hormone Antagonists
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
CHEBI has role CHEBI:50266 prodrug
CHEBI has role CHEBI:35610 antineoplastic agent
MeSH PA D065088 Steroid Synthesis Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Malignant tumor of prostate indication 399068003 DOID:10283
Hyperbilirubinemia contraindication 14783006 DOID:2741
Hypertensive disorder contraindication 38341003 DOID:10763
Hypokalemia contraindication 43339004
Body fluid retention contraindication 43498006
Chronic heart failure contraindication 48447003
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.68 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
500MG ZYTIGA JANSSEN BIOTECH N202379 April 14, 2017 RX TABLET ORAL 8822438 Aug. 24, 2027 USE IN COMBINATION WITH PREDNISONE FOR THE TREATMENT OF PATIENTS WITH METASTATIC CASTRATION-RESISTANT PROSTATE CANCER
500MG ZYTIGA JANSSEN BIOTECH N202379 April 14, 2017 RX TABLET ORAL 8822438 Aug. 24, 2027 USE IN COMBINATION WITH PREDNISONE FOR THE TREATMENT OF PATIENTS WITH METASTATIC CASTRATION-RESISTANT PROSTATE CANCER WHO HAD RECEIVED PRIOR DOCETAXEL CHEMOTHERAPY
500MG ZYTIGA JANSSEN BIOTECH N202379 April 14, 2017 RX TABLET ORAL 8822438 Aug. 24, 2027 USE IN COMBINATION WITH PREDNISONE FOR THE TREATMENT OF PATIENTS WITH METASTATIC HIGH-RISK CASTRATION-SENSITIVE PROSTATE CANCER
125MG YONSA SUN PHARMA GLOBAL N210308 May 22, 2018 RX TABLET ORAL 10292990 May 20, 2034 USE IN COMBINATION WITH METHYLPREDNISOLONE FOR THE TREATMENT OF PATIENTS WITH PROSTATE CANCER

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
250MG ZYTIGA JANSSEN BIOTECH N202379 April 28, 2011 RX TABLET ORAL Feb. 7, 2021 ABIRATERONE ACETATE IN COMBINATION WITH PREDNISONE FOR THE TREATMENT OF PATIENTS WITH METASTATIC HIGH-RISK CASTRATION-SENSITIVE PROSTATE CANCER
500MG ZYTIGA JANSSEN BIOTECH N202379 April 14, 2017 RX TABLET ORAL Feb. 7, 2021 ABIRATERONE ACETATE IN COMBINATION WITH PREDNISONE FOR THE TREATMENT OF PATIENTS WITH METASTATIC HIGH-RISK CASTRATION-SENSITIVE PROSTATE CANCER

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Steroid 17-alpha-hydroxylase/17,20 lyase Enzyme INHIBITOR IC50 8.54 CHEMBL IUPHAR
Cytochrome P450 3A4 Enzyme IC50 5.57 CHEMBL
Cytochrome P450 11B1, mitochondrial Enzyme IC50 5.79 CHEMBL
Cytochrome P450 11B2, mitochondrial Enzyme IC50 5.76 CHEMBL
Cytochrome P450 17A1 Enzyme IC50 7.90 CHEMBL

External reference:

IDSource
D000069501 MESH_DESCRIPTOR_UI
4030721 VUID
N0000182731 NUI
C2607886 UMLSCUI
D09701 KEGG_DRUG
299803 MMSL
1100071 RXNORM
27860 MMSL
013721 NDDF
4030721 VANDF
699679004 SNOMEDCT_US
CHEMBL254328 ChEMBL_ID
CHEMBL271227 ChEMBL_ID
EM5OCB9YJ6 UNII
7375 INN_ID
154229-19-3 SECONDARY_CAS_RN
AER PDB_CHEM_ID
CHEBI:68639 CHEBI
9288 IUPHAR_LIGAND_ID
DB05812 DRUGBANK_ID
9821849 PUBCHEM_CID
C089740 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Abiraterone Acetate HUMAN PRESCRIPTION DRUG LABEL 1 0093-1125 TABLET, FILM COATED 250 mg ORAL ANDA 18 sections
Abiraterone HUMAN PRESCRIPTION DRUG LABEL 1 0143-9597 TABLET 250 mg ORAL ANDA 19 sections
Abiraterone Acetate HUMAN PRESCRIPTION DRUG LABEL 1 0378-6920 TABLET 250 mg ORAL ANDA 18 sections
Abiraterone Acetate HUMAN PRESCRIPTION DRUG LABEL 1 0378-6924 TABLET, FILM COATED 250 mg ORAL ANDA 18 sections
Abiraterone Acetate HUMAN PRESCRIPTION DRUG LABEL 1 42291-024 TABLET 250 mg ORAL ANDA 18 sections
YONSA HUMAN PRESCRIPTION DRUG LABEL 1 47335-401 TABLET 125 mg ORAL NDA 17 sections
Abiraterone Acetate HUMAN PRESCRIPTION DRUG LABEL 1 51407-181 TABLET 250 mg ORAL ANDA 18 sections
Zytiga HUMAN PRESCRIPTION DRUG LABEL 1 57894-150 TABLET 250 mg ORAL NDA 19 sections
Abiraterone acetate HUMAN PRESCRIPTION DRUG LABEL 1 57894-155 TABLET 250 mg ORAL NDA AUTHORIZED GENERIC 19 sections
Zytiga HUMAN PRESCRIPTION DRUG LABEL 1 57894-184 TABLET, FILM COATED 250 mg ORAL NDA 19 sections
Zytiga HUMAN PRESCRIPTION DRUG LABEL 1 57894-195 TABLET, FILM COATED 500 mg ORAL NDA 19 sections
Abiraterone acetate HUMAN PRESCRIPTION DRUG LABEL 1 57894-199 TABLET, FILM COATED 500 mg ORAL NDA 19 sections
Abiraterone Acetate HUMAN PRESCRIPTION DRUG LABEL 1 60505-4327 TABLET 250 mg ORAL ANDA 18 sections
Abiraterone Acetate HUMAN PRESCRIPTION DRUG LABEL 1 60687-455 TABLET 250 mg ORAL ANDA 19 sections
Abiraterone acetate HUMAN PRESCRIPTION DRUG LABEL 1 64679-021 TABLET 250 mg ORAL ANDA 18 sections
Abiraterone acetate HUMAN PRESCRIPTION DRUG LABEL 1 64980-418 TABLET 250 mg ORAL ANDA 18 sections
Abiraterone Acetate HUMAN PRESCRIPTION DRUG LABEL 1 69238-1165 TABLET 250 mg ORAL ANDA 18 sections
Abiraterone HUMAN PRESCRIPTION DRUG LABEL 1 69539-049 TABLET 250 mg ORAL ANDA 18 sections
Abiraterone HUMAN PRESCRIPTION DRUG LABEL 1 72205-030 TABLET 250 mg ORAL ANDA 18 sections
Abiraterone acetate HUMAN PRESCRIPTION DRUG LABEL 1 72606-566 TABLET 250 mg ORAL ANDA 18 sections