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

Stem definitionDrug idCAS RN
non-steroid antiandrogens 367 90357-06-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ICI 176334
  • ICI-176334
  • bicalutamide
  • casodex
Bicalutamide is a non-steroidal androgen receptor inhibitor. It competitively inhibits the action of androgens by binding to cytosol androgen receptors in the target tissue. Prostatic carcinoma is known to be androgen sensitive and responds to treatment that counteracts the effect of androgen and/or removes the source of androgen.
  • Molecular weight: 430.37
  • Formula: C18H14F4N2O4S
  • CLOGP: 2.71
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 107.26
  • ALOGS: -4.67
  • ROTB: 6

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
50 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.94 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Oct. 4, 1995 FDA ASTRAZENECA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC L02AE51 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ENDOCRINE THERAPY
HORMONES AND RELATED AGENTS
Gonadotropin releasing hormone analogues
ATC L02BB03 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
CHEBI has role CHEBI:35497 antiandrogen
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:35703 xenobiotic
CHEBI has role CHEBI:78298 environmental contaminants
MeSH PA D000726 Androgen Antagonists
MeSH PA D000970 Antineoplastic Agents
MeSH PA D006727 Hormone Antagonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Metastatic Prostate Carcinoma indication
Advanced Prostatic Carcinoma off-label use
Interstitial pneumonia contraindication 64667001
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Drug-induced hepatitis contraindication 235876009
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.19 acidic
pKa2 11.84 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Androgen receptor Nuclear hormone receptor ANTAGONIST Ki 7.72 CHEMBL CHEMBL
Cytochrome P450 2C19 Enzyme IC50 6 CHEMBL
Progesterone receptor Transcription factor IC50 5.25 CHEMBL
Progesterone receptor Transcription factor Ki 5.14 CHEMBL
Androgen receptor Transcription factor IC50 6.17 CHEMBL
Androgen receptor Transcription factor Ki 7.85 CHEMBL

External reference:

IDSource
A0Z3NULLU9DP UNII
4020950 VUID
N0000148428 NUI
D00961 KEGG_DRUG
4020950 VANDF
C0285590 UMLSCUI
CHEBI:3090 CHEBI
CHEMBL409 ChEMBL_ID
CHEMBL63560 ChEMBL_ID
DB01128 DRUGBANK_ID
7021 INN_ID
C053541 MESH_SUPPLEMENTAL_RECORD_UI
2375 PUBCHEM_CID
2863 IUPHAR_LIGAND_ID
151495 RXNORM
165839 MMSL
4282 MMSL
4824 MMSL
d03850 MMSL
005064 NDDF
108766001 SNOMEDCT_US
386908000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 0904-6019 TABLET 50 mg ORAL ANDA 26 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 16714-816 TABLET, FILM COATED 50 mg ORAL ANDA 28 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 16729-023 TABLET 50 mg ORAL ANDA 26 sections
bicalutamide Human Prescription Drug Label 1 47335-485 TABLET, FILM COATED 50 mg ORAL ANDA 26 sections
CASODEX HUMAN PRESCRIPTION DRUG LABEL 1 54868-4503 TABLET 50 mg ORAL NDA 25 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 54868-6133 TABLET, FILM COATED 50 mg ORAL ANDA 28 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 60429-177 TABLET, FILM COATED 50 mg ORAL ANDA 26 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 60505-2642 TABLET 50 mg ORAL ANDA 26 sections
bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 62175-132 TABLET, FILM COATED 50 mg ORAL ANDA 26 sections
CASODEX HUMAN PRESCRIPTION DRUG LABEL 1 62559-680 TABLET 50 mg ORAL NDA 27 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 62559-890 TABLET 50 mg ORAL NDA 27 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 63629-8308 TABLET 50 mg ORAL ANDA 25 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 63672-0005 TABLET, FILM COATED 50 mg ORAL ANDA 28 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 65841-613 TABLET, FILM COATED 50 mg ORAL ANDA 1 sections
bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 67253-191 TABLET, FILM COATED 50 mg ORAL ANDA 28 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 68382-224 TABLET, FILM COATED 50 mg ORAL ANDA 28 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 70518-2993 TABLET 50 mg ORAL ANDA 25 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 71205-577 TABLET 50 mg ORAL ANDA 26 sections