Identification

Name
Bicalutamide
Accession Number
DB01128  (APRD00042, DB06284)
Type
Small Molecule
Groups
Approved
Description

Bicalutamide is an oral non-steroidal anti-androgen for prostate cancer. It is a racemic mixture consisting of equal proportions of enantiomers (R)-bicalutamide and (S)-bicalutamide. Bicalutamide binds to the androgen receptor.

Structure
Thumb
Synonyms
  • Bicalutamida
  • Bicalutamide
  • Bicalutamidum
External IDs
ICI 176,334 / ICI-176334 / ICI176,334-1
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Accel-bicalutamide Tablets USPTablet50 mgOralAccel Pharma IncNot applicableNot applicableCanada
Ach-bicalutamideTablet50 mgOralAccord Healthcare Limited2010-05-05Not 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 mgOralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
BicalutamideTablet50 mgOralSorres Pharma Inc2009-06-222014-06-20Canada
Bicalutamide TabletsTablet50 mgOralFresenius KabiNot applicableNot applicableCanada
CasodexTablet50 mg/1OralAstra Zeneca Lp1995-10-16Not applicableUs
CasodexTablet50 mg/1OralPhysicians Total Care, Inc.2002-06-04Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-bicalutamideTablet50 mgOralApotex Corporation2007-11-05Not applicableCanada
BicalutamideTablet, film coated50 mg/1OralAv Kare, Inc.2014-01-13Not applicableUs
BicalutamideTablet50 mg/1OralMajor2010-05-11Not applicableUs
BicalutamideTablet, film coated50 mg/1OralCadila Pharnmaceuticals2009-07-06Not applicableUs
BicalutamideTablet, film coated50 mg/1OralAvera Mc Kennan Hospital2015-03-01Not applicableUs
BicalutamideTablet, film coated50 mg/1OralGolden State Medical Supply2014-05-08Not applicableUs16729 0023 10 nlmimage10 82464162
BicalutamideTablet50 mg/1OralRemedy Repack2013-09-192016-04-05Us
BicalutamideTablet, film coated50 mg/1OralZydus Pharmaceuticals Usa, Inc.2009-07-06Not applicableUs
BicalutamideTablet50 mg/1OralApotex Corporation2009-07-06Not applicableUs
BicalutamideTablet, film coated50 mg/1OralMylan Pharmaceuticals2009-07-06Not applicableUs
Categories
UNII
A0Z3NAU9DP
CAS number
90357-06-5
Weight
Average: 430.373
Monoisotopic: 430.061040456
Chemical Formula
C18H14F4N2O4S
InChI Key
LKJPYSCBVHEWIU-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

Indication

For treatment (together with surgery or LHRH analogue) of advanced prostatic cancer.

Structured Indications
Pharmacodynamics

Bicalutamide 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 action

Bicalutamide 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.

TargetActionsOrganism
AAndrogen receptor
antagonist
Human
Absorption

Bicalutamide is well-absorbed following oral administration, although the absolute bioavailability is unknown.

Volume of distribution
Not Available
Protein binding

96%

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 elimination
Not Available
Half life

5.9 days

Clearance
  • Apparent oral cl=0.32 L/h [Normal Males]
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not 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
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Bicalutamide.Experimental
AmiodaroneThe metabolism of Bicalutamide can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Bicalutamide can be increased when it is combined with Aprepitant.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
AtorvastatinThe risk or severity of adverse effects can be increased when Bicalutamide is combined with Atorvastatin.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Bicalutamide.Approved, Investigational
BoceprevirThe metabolism of Bicalutamide can be decreased when combined with Boceprevir.Approved, Withdrawn
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
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Bicalutamide.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Bicalutamide.Approved
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Bicalutamide.Approved
Capromab pendetideBicalutamide may decrease effectiveness of Capromab pendetide as a diagnostic agent.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
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Bicalutamide.Withdrawn
Choline C 11The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Bicalutamide.Approved, Investigational
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
ClorindioneThe serum concentration of Clorindione can be increased when it is combined with Bicalutamide.Experimental
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
CymarinCymarin may decrease the cardiotoxic activities of Bicalutamide.Experimental
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
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Bicalutamide.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Bicalutamide.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Bicalutamide.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Bicalutamide.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Bicalutamide.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Bicalutamide.Experimental
DihydroergotamineThe metabolism of Bicalutamide can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Bicalutamide can be decreased when combined with Diltiazem.Approved
DiphenadioneThe serum concentration of Diphenadione can be increased when it is combined with Bicalutamide.Experimental
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Bicalutamide.Approved, Investigational
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
EnzalutamideThe serum concentration of Bicalutamide can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Bicalutamide.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Bicalutamide.Approved
ErythromycinThe metabolism of Bicalutamide can be decreased when combined with Erythromycin.Approved, Vet Approved
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Bicalutamide.Withdrawn
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination 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
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Bicalutamide.Approved
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
GitoformateGitoformate may decrease the cardiotoxic activities of Bicalutamide.Experimental
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
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Bicalutamide.Experimental
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Bicalutamide.Approved, Investigational
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
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Bicalutamide.Illicit, Investigational, Withdrawn
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Bicalutamide.Experimental
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Bicalutamide.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Bicalutamide.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Bicalutamide.Experimental
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Bicalutamide.Approved, Investigational
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Bicalutamide.Experimental
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
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
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Bicalutamide.Approved, Investigational
NilotinibThe metabolism of Bicalutamide can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Bicalutamide can be decreased when combined with Olaparib.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Bicalutamide.Experimental, Investigational
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
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Bicalutamide.Approved, Investigational, Vet Approved, Withdrawn
PeruvosidePeruvoside may decrease the cardiotoxic activities of Bicalutamide.Experimental
PhenindioneThe serum concentration of Phenindione can be increased when it is combined with Bicalutamide.Approved, Investigational
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, Investigational
PhenytoinThe metabolism of Bicalutamide can be increased when combined with Phenytoin.Approved, Vet Approved
PitavastatinThe serum concentration of Pitavastatin 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
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Bicalutamide.Approved
PrimidoneThe metabolism of Bicalutamide can be increased when combined with Primidone.Approved, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Bicalutamide.Experimental
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
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Bicalutamide.Approved
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
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Bicalutamide.Approved
St. John's WortThe serum concentration of Bicalutamide can be decreased when it is combined with St. John's Wort.Investigational, 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, Withdrawn
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
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Bicalutamide.Experimental
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Bicalutamide.Approved, Withdrawn
TiclopidineThe metabolism of Bicalutamide can be decreased when combined with Ticlopidine.Approved
TioclomarolThe serum concentration of Tioclomarol can be increased when it is combined with Bicalutamide.Experimental
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
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Bicalutamide.Approved, Experimental
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 References
Not Available
External Links
Human Metabolome Database
HMDB15260
KEGG Drug
D00961
KEGG Compound
C08160
PubChem Compound
2375
PubChem Substance
46505386
ChemSpider
2284
BindingDB
18525
ChEBI
91617
ChEMBL
CHEMBL409
Therapeutic Targets Database
DAP000092
PharmGKB
PA164746255
IUPHAR
2863
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Bicalutamide
ATC Codes
L02BB03 — Bicalutamide
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
FDA label
Download (182 KB)
MSDS
Download (57.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentAdenocarcinoma of the Prostate / Hormone-Resistant Prostate Cancer / Prostate Cancer / Stage IV Prostate Cancer1
1Active Not RecruitingTreatmentProstate Cancer2
1CompletedNot AvailableHealthy Volunteers2
1CompletedPreventionHealthy Volunteers1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentProstate Cancer5
1TerminatedTreatmentAdenocarcinoma of the Prostate / Recurrent Prostate Cancer1
1TerminatedTreatmentHealthy Volunteers2
1TerminatedTreatmentNon Castrate Metastatic Prostate Cancer1
1TerminatedTreatmentProstate Cancer1
1, 2Active Not RecruitingTreatmentProstate Cancer1
1, 2CompletedTreatmentProstate Cancer / Prostatic Neoplasms1
1, 2CompletedTreatmentProstatic Neoplasms1
1, 2RecruitingTreatmentAdenocarcinoma, Prostate / Stage I Prostate Cancer / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer / Stage III Prostate Cancer1
1, 2RecruitingTreatmentMetastatic Breast Cancer (MBC)1
1, 2RecruitingTreatmentTriple Negative Breast Cancer (TNBC)1
1, 2TerminatedTreatmentAndrogen-insensitive Prostate Cancer / Castrate-resistant Prostate Cancer (CRPC) / Hormone-Refractory Prostate Cancer / Metastatic Disease / Prostate Cancer / Prostatic Neoplasms1
1, 2TerminatedTreatmentProstate Cancer1
2Active Not RecruitingTreatmentAdenocarcinoma, Prostate / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer1
2Active Not RecruitingTreatmentCancer, Breast1
2Active Not RecruitingTreatmentErectile Dysfunction (ED) / Lower Urinary Tract Symptoms (LUTS) / Prostate Cancer1
2Active Not RecruitingTreatmentHormone-Resistant Prostate Cancer / Recurrent Prostate Carcinoma1
2Active Not RecruitingTreatmentProstate Cancer5
2Active Not RecruitingTreatmentProstatic Neoplasms1
2Active Not RecruitingTreatmentPuberty, Precocious1
2Active Not RecruitingTreatmentRecurrent Prostate Carcinoma / Stage I Prostate Cancer / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer / Stage III Prostate Cancer1
2CompletedTreatmentAdenocarcinoma of the Prostate / Prostate Cancer1
2CompletedTreatmentAdenocarcinoma of the Prostate / Stage IV Prostate Cancer1
2CompletedTreatmentAdenocarcinoma, Prostate / Stage I Prostate Cancer / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer / Stage III Prostate Cancer1
2CompletedTreatmentCancer, Ovarian / Fallopian Tube Cancer / Primary Peritoneal Cavity Cancer1
2CompletedTreatmentCancers / Hormonal Cycling / Prostate1
2CompletedTreatmentGynaecomastia / Prostate Cancer1
2CompletedTreatmentProstate Cancer15
2CompletedTreatmentRecurrent Prostate Carcinoma / Stage I Prostate Cancer / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer / Stage III Prostate Cancer1
2Not Yet RecruitingTreatmentNeoplasms, Breast1
2Not Yet RecruitingTreatmentProstate Cancer1
2RecruitingTreatmentAdenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
2RecruitingTreatmentBone Metastases / Prostate Cancer / Prostate Neoplasms1
2RecruitingTreatmentCancer, Breast2
2RecruitingTreatmentMetastatic Breast Cancer (MBC)1
2RecruitingTreatmentProstate Cancer4
2RecruitingTreatmentSalivary Gland Cancers1
2RecruitingTreatmentStage I Prostate Adenocarcinoma / Stage II Prostate Adenocarcinoma1
2TerminatedTreatmentAdenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
2TerminatedTreatmentCancer, Breast1
2TerminatedTreatmentProstate Cancer2
2TerminatedTreatmentProstatic Neoplasms1
2Unknown StatusTreatmentProstate Cancer1
2WithdrawnNot AvailableProstate Cancer1
2WithdrawnTreatmentAdenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage III Prostate Cancer / Stage IV Prostate Cancer1
2WithdrawnTreatmentProstate Cancer4
2, 3CompletedNot AvailableProstate Cancer1
2, 3RecruitingTreatmentStage I Prostate Adenocarcinoma / Stage II Prostate Adenocarcinoma / Stage III Prostate Adenocarcinoma1
3Active Not RecruitingTreatmentGastrointestinal Complications / Prostate Cancer / Sexual Dysfunctions / Urinary Complications1
3Active Not RecruitingTreatmentProstate Cancer7
3CompletedHealth Services ResearchProstate Cancer1
3CompletedPreventionProstate Cancer1
3CompletedTreatmentNon-Metastatic Prostate Cancer3
3CompletedTreatmentProstate Cancer14
3RecruitingPreventionMetastatic Triple Negative Breast Cancer1
3RecruitingTreatmentProstatic Neoplasms1
3TerminatedTreatmentProstate Cancer6
3TerminatedTreatmentProstatic Neoplasms1
3Unknown StatusTreatmentProstate Cancer2
4CompletedTreatmentProstate Cancer1
4CompletedTreatmentProstate Neoplasms1
4WithdrawnTreatmentMetastatic Hormone Refractory Prostate Cancer1
Not AvailableActive Not RecruitingNot AvailableProstate Cancer1
Not AvailableActive Not RecruitingTreatmentStage III Prostate Cancer1
Not AvailableCompletedPreventionBone destruction1
Not AvailableCompletedTreatmentProstatic Neoplasms1
Not AvailableNo Longer AvailableNot AvailableAdenocarcinoma of the Prostate1
Not AvailableNot Yet RecruitingTreatmentStage IV Prostate Cancer1
Not AvailableRecruitingNot AvailableProstate Cancer1
Not AvailableRecruitingTreatmentAdenocarcinoma of the Prostate1
Not AvailableRecruitingTreatmentProstate Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
TabletOral50 mg/1
Tablet, film coatedOral50 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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)191-193 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4r-0890000000-f2bd2727ffd1da47c463
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014r-2950100000-4088c17274bcf0f095d4
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014r-0980100000-89a3faa58e22068394b8

Taxonomy

Description
This compound belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Trifluoromethylbenzenes
Direct Parent
Trifluoromethylbenzenes
Alternative Parents
Anilides / Benzenesulfonyl compounds / Benzonitriles / N-arylamides / Fluorobenzenes / Aryl fluorides / Tertiary alcohols / Sulfones / Secondary carboxylic acid amides / Nitriles
show 6 more
Substituents
Trifluoromethylbenzene / Benzenesulfonyl group / Anilide / Benzonitrile / N-arylamide / Fluorobenzene / Halobenzene / Aryl fluoride / Aryl halide / Tertiary alcohol
show 22 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Androgen receptor
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 ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
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
Substrate
Inhibitor
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Cockshott ID: Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78. [PubMed:15509184]

Drug created on June 13, 2005 07:24 / Updated on November 13, 2017 21:49