enzalutamide Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
non-steroid antiandrogens 4628 915087-33-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • enzalutamide
  • xtandi
  • MDV3100
  • MDV-3100
Enzalutamide is an androgen receptor inhibitor that acts on different steps in the androgen receptor signaling pathway. Enzalutamide has been shown to competitively inhibit androgen binding to androgen receptors and inhibit androgen receptor nuclear translocation and interaction with DNA. A major metabolite, N‑desmethyl enzalutamide, exhibited similar in vitro activity to enzalutamide. Enzalutamide decreased proliferation and induced cell death of prostate cancer cells in vitro, and decreased tumor volume in a mouse prostate cancer xenograft model.
  • Molecular weight: 464.44
  • Formula: C21H16F4N4O2S
  • CLOGP: 3.35
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 1
  • TPSA: 76.44
  • ALOGS: -5.53
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.16 g O

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
Aug. 31, 2012 FDA ASTELLAS
March 24, 2014 PMDA Astellas Pharma Inc

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC L02BB04 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ENDOCRINE THERAPY
HORMONE ANTAGONISTS AND RELATED AGENTS
Anti-androgens
FDA MoA N0000000243 Androgen Receptor Antagonists
FDA EPC N0000175560 Androgen Receptor Inhibitor
FDA MoA N0000185506 Cytochrome P450 3A4 Inducers
FDA MoA N0000185507 Cytochrome P450 2C9 Inducers
FDA MoA N0000185607 Cytochrome P450 2C19 Inducers
CHEBI has role CHEBI:35497 antiandrogen
CHEBI has role CHEBI:35610 cytostatic

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Metastasis from malignant tumor of prostate indication 314994000
Malignant tumor of prostate indication 399068003 DOID:10283

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.88 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
40MG XTANDI ASTELLAS N203415 Aug. 31, 2012 RX CAPSULE ORAL July 13, 2021 TREATMENT OF PATIENTS WITH NON-METASTATIC CASTRATION-RESISTANT PROSTATE CANCER
40MG XTANDI ASTELLAS N213674 Aug. 4, 2020 RX TABLET ORAL July 13, 2021 TREATMENT OF PATIENTS WITH NON-METASTATIC CASTRATION-RESISTANT PROSTATE CANCER
80MG XTANDI ASTELLAS N213674 Aug. 4, 2020 RX TABLET ORAL July 13, 2021 TREATMENT OF PATIENTS WITH NON-METASTATIC CASTRATION-RESISTANT PROSTATE CANCER
40MG XTANDI ASTELLAS N203415 Aug. 31, 2012 RX CAPSULE ORAL Dec. 16, 2022 TREATMENT OF PATIENTS WITH METASTATIC CASTRATION-SENSITIVE PROSTATE CANCER (MCSPC)
40MG XTANDI ASTELLAS N213674 Aug. 4, 2020 RX TABLET ORAL Dec. 16, 2022 TREATMENT OF PATIENTS WITH METASTATIC CASTRATION-SENSITIVE PROSTATE CANCER (MCSPC)
80MG XTANDI ASTELLAS N213674 Aug. 4, 2020 RX TABLET ORAL Dec. 16, 2022 TREATMENT OF PATIENTS WITH METASTATIC CASTRATION-SENSITIVE PROSTATE CANCER (MCSPC)

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Androgen receptor Nuclear hormone receptor ANTAGONIST EC50 7.31 CHEMBL CHEMBL

External reference:

IDSource
D10218 KEGG_DRUG
4031716 VUID
N0000185726 NUI
4031716 VANDF
C3496793 UMLSCUI
CHEBI:68534 CHEBI
CHEMBL1082407 ChEMBL_ID
DB08899 DRUGBANK_ID
C540278 MESH_SUPPLEMENTAL_RECORD_UI
15951529 PUBCHEM_CID
6812 IUPHAR_LIGAND_ID
9621 INN_ID
93T0T9GKNU UNII
1307298 RXNORM
192757 MMSL
28802 MMSL
d07900 MMSL
014630 NDDF
703125003 SNOMEDCT_US
703684000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Xtandi HUMAN PRESCRIPTION DRUG LABEL 1 0469-0125 CAPSULE 40 mg ORAL NDA 28 sections
Xtandi HUMAN PRESCRIPTION DRUG LABEL 1 0469-0625 TABLET 40 mg ORAL NDA 28 sections
Xtandi HUMAN PRESCRIPTION DRUG LABEL 1 0469-0725 TABLET 80 mg ORAL NDA 28 sections