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Identification
NameBicalutamide
Accession NumberDB01128  (APRD00042, DB06284)
TypeSmall Molecule
GroupsApproved
DescriptionBicalutamide is an oral non-steroidal anti-androgen for prostate cancer. It binds to the androgen receptor.
Structure
Thumb
Synonyms
Casodex
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Accel-bicalutamide Tablets USPTablet50 mgOralAccel Pharma IncNot applicableNot applicableCanada
Ach-bicalutamideTablet50 mgOralAccord Healthcare Inc2010-05-05Not applicableCanada
Act BicalutamideTablet50 mgOralActavis Pharma Company2006-02-07Not applicableCanada
Ag-bicalutamideTablet50 mgOralAngita Pharma Inc.Not applicableNot applicableCanada
Ava-bicalutamideTablet50 mgOralAvanstra Inc2011-11-232014-08-21Canada
BicalutamideTablet50 mgOralSorres Pharma Inc2009-06-222014-06-20Canada
BicalutamideTablet50 mgOralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
Bicalutamide TabletsTablet50 mgOralFresenius Kabi Canada LtdNot applicableNot applicableCanada
CasodexTablet50 mg/1OralAstra Zeneca Pharmaceuticals Lp1995-10-16Not applicableUs
CasodexTablet50 mg/1OralPhysicians Total Care, Inc.2002-06-04Not applicableUs
Casodex Tab 50mgTablet50 mgOralAstrazeneca Canada Inc1996-12-31Not applicableCanada
Dom-bicalutamideTablet50 mgOralDominion Pharmacal2008-04-16Not applicableCanada
Jamp-bicalutamideTablet50 mgOralJamp Pharma Corporation2010-10-21Not applicableCanada
Med-bicalutamideTablet50 mgOralGeneric Medical Partners IncNot applicableNot applicableCanada
Mylan-bicalutamideTablet50 mgOralMylan Pharmaceuticals Ulc2007-12-20Not applicableCanada
Ntp-bicalutamideTablet50 mgOralTeva Canada LimitedNot applicableNot applicableCanada
Nu-bicalutamideTablet50 mgOralNu Pharm IncNot applicableNot applicableCanada
PHL-bicalutamideTablet50 mgOralPharmel Inc2006-07-21Not applicableCanada
PMS-bicalutamideTablet50 mgOralPharmascience Inc2006-02-08Not applicableCanada
Pro-bicalutamide - 50Tablet50 mgOralPro Doc Limitee2008-07-09Not applicableCanada
Ran-bicalutamideTablet50 mgOralRanbaxy Pharmaceuticals Canada Inc.2012-09-07Not applicableCanada
Ratio-bicalutamideTablet50 mgOralRatiopharm Inc Division Of Teva Canada Limited2006-03-132014-09-19Canada
Sandoz BicalutamideTablet50 mgOralSandoz Canada Incorporated2006-02-08Not applicableCanada
Teva-bicalutamideTablet50 mgOralTeva Canada Limited2006-02-10Not applicableCanada
Van-bicalutamideTablet50 mgOralVanc Pharmaceuticals Inc2015-06-22Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-bicalutamideTablet50 mgOralApotex Inc2007-11-05Not applicableCanada
BicalutamideTablet, film coated50 mg/1OralPhysicians Total Care, Inc.2010-08-09Not applicableUs
BicalutamideTablet50 mg/1OralAccord Healthcare Inc.2009-07-06Not applicableUs
BicalutamideTablet50 mg/1OralSandoz Inc2009-07-06Not applicableUs
BicalutamideTablet50 mg/1OralAmerican Health Packaging2012-11-292016-09-30Us
BicalutamideTablet50 mg/1Oralbryant ranch prepack2009-07-06Not applicableUs
BicalutamideTablet, film coated50 mg/1OralTeva Pharmaceuticals USA Inc2009-07-06Not applicableUs
BicalutamideTablet, film coated50 mg/1OralSun Pharma Global FZE2014-12-15Not applicableUs
BicalutamideTablet, film coated50 mg/1OralGolden State Medical Supply, Inc.2014-05-08Not applicableUs
BicalutamideTablet, film coated50 mg/1OralZydus Pharmaceuticals (USA) Inc.2009-07-06Not applicableUs
BicalutamideTablet, film coated50 mg/1OralNorthstar Rx LLC2009-08-28Not applicableUs
BicalutamideTablet, film coated50 mg/1OralSynthon Pharmaceuticals, Inc.2009-07-06Not applicableUs
BicalutamideTablet, film coated50 mg/1OralBreckenridge Pharmaceutical, Inc.2010-11-16Not applicableUs
BicalutamideTablet, film coated50 mg/1OralMylan Pharmaceuticals Inc2009-07-06Not applicableUs
BicalutamideTablet, film coated50 mg/1OralGolden State Medical Supply, Inc.2010-11-16Not applicableUs
BicalutamideTablet, film coated50 mg/1OralAvera Mc Kennan Hospital2015-03-01Not applicableUs
BicalutamideTablet50 mg/1OralSun Pharma Global Inc.2009-07-07Not applicableUs
BicalutamideTablet, film coated50 mg/1OralCadila Healthcare Limited2009-07-06Not applicableUs
BicalutamideTablet50 mg/1OralREMEDYREPACK INC.2013-09-192016-04-05Us
BicalutamideTablet50 mg/1OralMajor Pharmaceuticals2010-05-11Not applicableUs
BicalutamideTablet50 mg/1OralApotex Corp.2009-07-06Not applicableUs
BicalutamideTablet, film coated50 mg/1OralAv Kare, Inc.2014-01-13Not applicableUs
BicalutamideTablet, film coated50 mg/1OralDAVA Pharmaceuticals, Inc.2009-07-06Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIA0Z3NAU9DP
CAS number90357-06-5
WeightAverage: 430.373
Monoisotopic: 430.061040456
Chemical FormulaC18H14F4N2O4S
InChI KeyLKJPYSCBVHEWIU-UHFFFAOYSA-N
InChI
InChI=1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)
IUPAC Name
N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide
SMILES
CC(O)(CS(=O)(=O)C1=CC=C(F)C=C1)C(=O)NC1=CC(=C(C=C1)C#N)C(F)(F)F
Pharmacology
IndicationFor treatment (together with surgery or LHRH analogue) of advanced prostatic cancer.
Structured Indications
PharmacodynamicsBicalutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Bicalutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Bicalutamide blocks the action of androgens of adrenal and testicular origin which stimulate the growth of normal and malignant prostatic tissue. Prostate cancer is mostly androgen-dependent and can be treated with surgical or chemical castration. To date, antiandrogen monotherapy has not consistently been shown to be equivalent to castration.
Mechanism of actionBicalutamide competes with androgen for the binding of androgen receptors, consequently blocking the action of androgens of adrenal and testicular origin which stimulate the growth of normal and malignant prostatic tissue.
TargetKindPharmacological actionActionsOrganismUniProt ID
Androgen receptorProteinyes
antagonist
HumanP10275 details
Related Articles
AbsorptionBicalutamide is well-absorbed following oral administration, although the absolute bioavailability is unknown.
Volume of distributionNot Available
Protein binding96%
Metabolism

Bicalutamide undergoes stereo specific metabolism. The S (inactive) isomer is metabolized primarily by glucuronidation. The R (active) isomer also undergoes glucuronidation but is predominantly oxidized to an inactive metabolite followed by glucuronidation.

Route of eliminationNot Available
Half life5.9 days
Clearance
  • Apparent oral cl=0.32 L/h [Normal Males]
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
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Bicalutamide.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Bicalutamide.Approved
AmiodaroneThe metabolism of Bicalutamide can be decreased when combined with Amiodarone.Approved, Investigational
AnvirzelAnvirzel may decrease the cardiotoxic activities of Bicalutamide.Investigational
AprepitantThe serum concentration of Bicalutamide can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Bicalutamide.Approved, Investigational
AstemizoleThe serum concentration of Astemizole can be increased when it is combined with Bicalutamide.Approved, Withdrawn
AtazanavirThe metabolism of Bicalutamide can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Bicalutamide can be decreased when combined with Atomoxetine.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Bicalutamide.Approved, Investigational
BexaroteneThe serum concentration of Bicalutamide can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Bicalutamide can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Bicalutamide can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Bicalutamide can be decreased when it is combined with Bosentan.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Bicalutamide.Approved
CarbamazepineThe metabolism of Bicalutamide can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Bicalutamide can be increased when it is combined with Ceritinib.Approved
Choline C 11The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Bicalutamide.Approved
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Bicalutamide.Approved
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Bicalutamide.Approved, Investigational, Withdrawn
ClarithromycinThe metabolism of Bicalutamide can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Bicalutamide can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Bicalutamide can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Bicalutamide can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Bicalutamide can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Bicalutamide can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Bicalutamide.Approved, Investigational
CyclosporineThe metabolism of Bicalutamide can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Bicalutamide can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Bicalutamide can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Bicalutamide can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Bicalutamide can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Bicalutamide can be decreased when combined with Delavirdine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Bicalutamide.Approved
DexamethasoneThe serum concentration of Bicalutamide can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Bicalutamide.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Bicalutamide.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Bicalutamide.Approved
DihydroergotamineThe metabolism of Bicalutamide can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Bicalutamide can be decreased when combined with Diltiazem.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Bicalutamide.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Bicalutamide.Approved
DoxycyclineThe metabolism of Bicalutamide can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Bicalutamide can be decreased when combined with Dronedarone.Approved
EfavirenzThe serum concentration of Bicalutamide can be decreased when it is combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Bicalutamide can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Bicalutamide can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Bicalutamide can be decreased when it is combined with Eslicarbazepine acetate.Approved
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Bicalutamide.Withdrawn
EtravirineThe serum concentration of Bicalutamide can be decreased when it is combined with Etravirine.Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Bicalutamide.Approved
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Bicalutamide.Approved
FluconazoleThe metabolism of Bicalutamide can be decreased when combined with Fluconazole.Approved
FluindioneThe serum concentration of Fluindione can be increased when it is combined with Bicalutamide.Investigational
FluvoxamineThe metabolism of Bicalutamide can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Bicalutamide can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Bicalutamide can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Bicalutamide can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Bicalutamide can be increased when it is combined with Fusidic Acid.Approved
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Bicalutamide.Approved, Illicit
IdelalisibThe serum concentration of Bicalutamide can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Bicalutamide can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Bicalutamide can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Bicalutamide can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Bicalutamide can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Bicalutamide can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Bicalutamide can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Bicalutamide can be decreased when combined with Ketoconazole.Approved, Investigational
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Bicalutamide.Approved
LopinavirThe metabolism of Bicalutamide can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Bicalutamide can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Bicalutamide can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Bicalutamide can be increased when combined with Lumacaftor.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Bicalutamide.Approved, Investigational
MifepristoneThe serum concentration of Bicalutamide can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Bicalutamide can be decreased when it is combined with Mitotane.Approved
ModafinilThe serum concentration of Bicalutamide can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Bicalutamide can be decreased when it is combined with Nafcillin.Approved
NefazodoneThe metabolism of Bicalutamide can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Bicalutamide can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Bicalutamide can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Bicalutamide can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Bicalutamide can be decreased when combined with Nilotinib.Approved, Investigational
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Bicalutamide.Approved
OlaparibThe metabolism of Bicalutamide can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Bicalutamide can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Bicalutamide.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Bicalutamide.Approved, Vet Approved
PalbociclibThe serum concentration of Bicalutamide can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Bicalutamide can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenindioneThe serum concentration of Phenindione can be increased when it is combined with Bicalutamide.Approved
PhenobarbitalThe metabolism of Bicalutamide can be increased when combined with Phenobarbital.Approved
PhenprocoumonThe serum concentration of Phenprocoumon can be increased when it is combined with Bicalutamide.Approved
PhenytoinThe metabolism of Bicalutamide can be increased when combined with Phenytoin.Approved, Vet Approved
PimozideThe serum concentration of Pimozide can be increased when it is combined with Bicalutamide.Approved
PosaconazoleThe metabolism of Bicalutamide can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Bicalutamide can be increased when combined with Primidone.Approved, Vet Approved
RanolazineThe metabolism of Bicalutamide can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Bicalutamide can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Bicalutamide can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Bicalutamide can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Bicalutamide can be decreased when combined with Ritonavir.Approved, Investigational
SaquinavirThe metabolism of Bicalutamide can be decreased when combined with Saquinavir.Approved, Investigational
SildenafilThe metabolism of Bicalutamide can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Bicalutamide can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Bicalutamide can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Bicalutamide can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Bicalutamide can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Bicalutamide can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Bicalutamide can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Bicalutamide can be decreased when combined with Telithromycin.Approved
TerfenadineThe serum concentration of Terfenadine can be increased when it is combined with Bicalutamide.Withdrawn
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Bicalutamide.Approved
TiclopidineThe metabolism of Bicalutamide can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Bicalutamide can be decreased when it is combined with Tocilizumab.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Bicalutamide.Approved, Investigational
VenlafaxineThe metabolism of Bicalutamide can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Bicalutamide can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Bicalutamide can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Bicalutamide.Approved
ZiprasidoneThe metabolism of Bicalutamide can be decreased when combined with Ziprasidone.Approved
Food Interactions
  • Take without regard to meals, at the same time everyday.
References
Synthesis Reference

Nnochiri Ekwuribe, “METHODS OF SYNTHESIZING ACYLANILIDES INCLUDING BICALUTAMIDE AND DERIVATIVES THEREOF.” U.S. Patent US20020165406, issued November 07, 2002.

US20020165406
General ReferencesNot Available
External Links
ATC CodesL02BB03
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelDownload (182 KB)
MSDSDownload (57.3 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9471
Blood Brain Barrier+0.859
Caco-2 permeable-0.6085
P-glycoprotein substrateNon-substrate0.6741
P-glycoprotein inhibitor INon-inhibitor0.7171
P-glycoprotein inhibitor IINon-inhibitor0.9178
Renal organic cation transporterNon-inhibitor0.9572
CYP450 2C9 substrateNon-substrate0.6883
CYP450 2D6 substrateNon-substrate0.8087
CYP450 3A4 substrateNon-substrate0.5536
CYP450 1A2 substrateNon-inhibitor0.8513
CYP450 2C9 inhibitorNon-inhibitor0.6246
CYP450 2D6 inhibitorNon-inhibitor0.8683
CYP450 2C19 inhibitorInhibitor0.7976
CYP450 3A4 inhibitorInhibitor0.7879
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5662
Ames testNon AMES toxic0.7134
CarcinogenicityNon-carcinogens0.6067
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4383 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9959
hERG inhibition (predictor II)Non-inhibitor0.8759
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tablet, film coatedOral50 mg/1
TabletOral50 mg/1
TabletOral50 mg
Prices
Unit descriptionCostUnit
Casodex 50 mg tablet20.19USD tablet
Bicalutamide 50 mg tablet18.92USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point191-193 °CNot Available
water solubility5 mg/LNot Available
logP2.5Not Available
pKa12.0Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00928 mg/mLALOGPS
logP2.7ALOGPS
logP2.71ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)11.95ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area107.26 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.59 m3·mol-1ChemAxon
Polarizability36.68 Å3ChemAxon
Number of Rings2ChemAxon
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-arylamides. These are organic compounds that contain a carboxamide group that is N-linked to a aryl group. They have the generic structure RC(=O)N(R')H, R = organyl group and R'= aryl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassN-arylamides
Sub ClassNot Available
Direct ParentN-arylamides
Alternative Parents
Substituents
  • N-arylamide
  • Benzonitrile
  • Halobenzene
  • Fluorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Tertiary alcohol
  • Sulfonyl
  • Sulfone
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Nitrile
  • Carbonitrile
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available

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. Wang LG, Liu XM, Kreis W, Budman DR: Androgen antagonistic effect of estramustine phosphate (EMP) metabolites on wild-type and mutated androgen receptor. Biochem Pharmacol. 1998 May 1;55(9):1427-33. [PubMed:10076535 ]
  2. Chang HC, Miyamoto H, Marwah P, Lardy H, Yeh S, Huang KE, Chang C: Suppression of Delta(5)-androstenediol-induced androgen receptor transactivation by selective steroids in human prostate cancer cells. Proc Natl Acad Sci U S A. 1999 Sep 28;96(20):11173-7. [PubMed:10500149 ]
  3. Laufer M, Sinibaldi VJ, Carducci MA, Eisenberger MA: Rapid disease progression after the administration of bicalutamide in patients with metastatic prostate cancer. Urology. 1999 Oct;54(4):745. [PubMed:10754148 ]
  4. Bouchal J, Kolar Z, Mad'arova J, Hlobilkova A, von Angerer E: The effects of natural ligands of hormone receptors and their antagonists on telomerase activity in the androgen sensitive prostatic cancer cell line LNCaP. Biochem Pharmacol. 2002 Mar 15;63(6):1177-81. [PubMed:11931851 ]
  5. Hara T, Miyazaki J, Araki H, Yamaoka M, Kanzaki N, Kusaka M, Miyamoto M: Novel mutations of androgen receptor: a possible mechanism of bicalutamide withdrawal syndrome. Cancer Res. 2003 Jan 1;63(1):149-53. [PubMed:12517791 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Cockshott ID: Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78. [PubMed:15509184 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Cockshott ID: Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78. [PubMed:15509184 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Cockshott ID: Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78. [PubMed:15509184 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Cockshott ID: Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78. [PubMed:15509184 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23