bicalutamide indications/contra

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

Drug dosage:

DoseUnitRoute
50 mg O

Approvals:

DateAgencyCompanyOrphan
Oct. 4, 1995 FDA ASTRAZENECA

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Interstitial lung disease 656.54 32.59 164 1716 13852 3370127
Dementia Alzheimer's type 579.01 32.59 98 1782 1119 3382860
Prostatic specific antigen increased 227.84 32.59 48 1832 1835 3382144
Hepatic function abnormal 204.64 32.59 63 1817 11164 3372815
Prostate cancer 149.52 32.59 39 1841 3781 3380198
Gynaecomastia 145.50 32.59 33 1847 1776 3382203
Cardiac failure 108.91 32.59 46 1834 20059 3363920
Malignant neoplasm progression 104.04 32.59 43 1837 17750 3366229
Hot flush 95.06 32.59 32 1848 7469 3376510
Haematuria 82.55 32.59 31 1849 9921 3374058
Dyspnoea 72.40 32.59 63 1817 102871 3281108
Metastases to bone 72.15 32.59 21 1859 3040 3380939
Anaemia 61.29 32.59 44 1836 54289 3329690
Platelet count decreased 60.53 32.59 34 1846 27434 3356545
Cerebral infarction 58.58 32.59 23 1857 8277 3375702
Hyperglycaemia 54.16 32.59 22 1858 8646 3375333
Drug-induced liver injury 53.81 32.59 19 1861 5094 3378885
Dehydration 51.63 32.59 33 1847 33616 3350363
Drug interaction 50.68 32.59 37 1843 46775 3337204
Asthenia 47.64 32.59 41 1839 65624 3318355
Breast cancer male 47.43 32.59 8 1872 87 3383892
Liver disorder 47.41 32.59 21 1859 10202 3373777
Prostate cancer metastatic 46.73 32.59 11 1869 694 3383285
Acute kidney injury 46.51 32.59 36 1844 49647 3334332
Hepatic failure 43.42 32.59 20 1860 10632 3373347
Product name confusion 41.44 32.59 8 1872 193 3383786
Hepatitis fulminant 41.37 32.59 11 1869 1140 3382839
Bone lesion 38.53 32.59 10 1870 943 3383036
Aspartate aminotransferase increased 38.16 32.59 23 1857 21090 3362889
International normalised ratio increased 37.42 32.59 20 1860 14595 3369384

Pharmacologic Action:

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SourceCodeDescription
ATC L02BB03 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ENDOCRINE THERAPY
HORMONE ANTAGONISTS AND RELATED AGENTS
Anti-androgens
MeSH PA D000726 Androgen Antagonists
MeSH PA D000970 Antineoplastic Agents
MeSH PA D006727 Hormone Antagonists
MeSH PA D006730 Hormones, Hormone Substitutes, and Hormone Antagonists
CHEBI has role CHEBI:35497 androgen antagonist
CHEBI has role CHEBI:35610 antineoplastic agent
FDA MoA N0000000243 Androgen Receptor Antagonists
FDA EPC N0000175560 Androgen Receptor Inhibitor

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Metastatic Prostate Carcinoma indication
Interstitial pneumonia contraindication 64667001 DOID:3082
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
Advanced Prostatic Carcinoma off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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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:

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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:

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IDSource
2863 IUPHAR_LIGAND_ID
4020950 VUID
N0000148428 NUI
C0285590 UMLSCUI
D00961 KEGG_DRUG
CHEMBL409 ChEMBL_ID
DB01128 DRUGBANK_ID
CHEMBL63560 ChEMBL_ID
4020950 VANDF
165839 MMSL
N0000007276 NDFRT
N0000148428 NDFRT
005064 NDDF
d03850 MMSL
4282 MMSL
83008 RXNORM
108766001 SNOMEDCT_US
386908000 SNOMEDCT_US
A0Z3NAU9DP UNII
7021 INN_ID
2375 PUBCHEM_CID
C053541 MESH_SUPPLEMENTAL_RECORD_UI
CHEBI:3090 CHEBI
0U9 PDB_CHEM_ID
198 PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 0093-0220 TABLET, FILM COATED 50 mg ORAL ANDA 18 sections
CASODEX HUMAN PRESCRIPTION DRUG LABEL 1 0310-0705 TABLET 50 mg ORAL NDA 17 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 0904-6019 TABLET 50 mg ORAL ANDA 18 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 16714-571 TABLET, FILM COATED 50 mg ORAL ANDA 19 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 16729-023 TABLET 50 mg ORAL ANDA 17 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 42291-168 TABLET, FILM COATED 50 mg ORAL ANDA 17 sections
bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 47335-485 TABLET, FILM COATED 50 mg ORAL ANDA 17 sections
CASODEX HUMAN PRESCRIPTION DRUG LABEL 1 54868-4503 TABLET 50 mg ORAL NDA 16 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 54868-6133 TABLET, FILM COATED 50 mg ORAL ANDA 17 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 60429-177 TABLET, FILM COATED 50 mg ORAL ANDA 17 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 60505-2642 TABLET 50 mg ORAL ANDA 17 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 63629-5321 TABLET 50 mg ORAL ANDA 18 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 63672-0005 TABLET, FILM COATED 50 mg ORAL ANDA 18 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 65841-613 TABLET, FILM COATED 50 mg ORAL ANDA 19 sections
bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 67253-191 TABLET, FILM COATED 50 mg ORAL ANDA 18 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 68382-224 TABLET, FILM COATED 50 mg ORAL ANDA 19 sections
Bicalutamide HUMAN PRESCRIPTION DRUG LABEL 1 69189-0298 TABLET, FILM COATED 50 mg ORAL ANDA 18 sections