Bicalutamide - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (1)Enzymes (4)

Targets (1)Enzymes (4)Biointeractions (6)

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Bicalutamida

Bicalutamide

Bicalutamidum

External IDs

ICI 176,334 / ICI-176334 / ICI176,334-1

Product Ingredients

Not Available

Product Images

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Accel-bicalutamide Tablets USP	Tablet	50 mg	Oral	Accel Pharma Inc	Not applicable	Not applicable	Canada
Ach-bicalutamide	Tablet	50 mg	Oral	Accord Healthcare Limited	2010-05-05	Not applicable	Canada
Act Bicalutamide	Tablet	50 mg	Oral	Actavis Pharma Company	2006-02-07	Not applicable	Canada
Ag-bicalutamide	Tablet	50 mg	Oral	Angita Pharma Inc.	Not applicable	Not applicable	Canada
Ava-bicalutamide	Tablet	50 mg	Oral	Avanstra Inc	2011-11-23	2014-08-21	Canada
Bicalutamide	Tablet	50 mg	Oral	Sorres Pharma Inc	2009-06-22	2014-06-20	Canada
Bicalutamide	Tablet	50 mg	Oral	Sivem Pharmaceuticals Ulc	2012-06-10	Not applicable	Canada
Bicalutamide Tablets	Tablet	50 mg	Oral	Fresenius Kabi	Not applicable	Not applicable	Canada
Casodex	Tablet	50 mg/1	Oral	Physicians Total Care, Inc.	2002-06-04	Not applicable	US
Casodex	Tablet	50 mg/1	Oral	Astra Zeneca Lp	1995-10-16	Not applicable	US
Casodex	Tablet	50 mg	Oral	Astra Zeneca	1996-12-31	Not applicable	Canada
Dom-bicalutamide	Tablet	50 mg	Oral	Dominion Pharmacal	2008-04-16	Not applicable	Canada
Jamp-bicalutamide	Tablet	50 mg	Oral	Jamp Pharma Corporation	2010-10-21	Not applicable	Canada
Med-bicalutamide	Tablet	50 mg	Oral	Generic Medical Partners Inc	Not applicable	Not applicable	Canada
Mylan-bicalutamide	Tablet	50 mg	Oral	Mylan Pharmaceuticals	2007-12-20	2017-01-09	Canada
Ntp-bicalutamide	Tablet	50 mg	Oral	Teva	Not applicable	Not applicable	Canada
Nu-bicalutamide	Tablet	50 mg	Oral	Nu Pharm Inc	Not applicable	Not applicable	Canada
PHL-bicalutamide	Tablet	50 mg	Oral	Pharmel Inc	2006-07-21	Not applicable	Canada
PMS-bicalutamide	Tablet	50 mg	Oral	Pharmascience Inc	2006-02-08	Not applicable	Canada
Pro-bicalutamide - 50	Tablet	50 mg	Oral	Pro Doc Limitee	2008-07-09	Not applicable	Canada
Ran-bicalutamide	Tablet	50 mg	Oral	Ranbaxy Inc.	2012-09-07	Not applicable	Canada
Ratio-bicalutamide	Tablet	50 mg	Oral	Ratiopharm Inc Division Of Teva Canada Limited	2006-03-13	2014-09-19	Canada
Sandoz Bicalutamide	Tablet	50 mg	Oral	Sandoz Canada Incorporated	2006-02-08	Not applicable	Canada
Teva-bicalutamide	Tablet	50 mg	Oral	Teva	2006-02-10	Not applicable	Canada
Van-bicalutamide	Tablet	50 mg	Oral	Vanc Pharmaceuticals Inc	2015-06-22	Not applicable	Canada

Approved Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-bicalutamide	Tablet	50 mg	Oral	Apotex Corporation	2007-11-05	Not applicable	Canada
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Zydus Pharmaceuticals Usa, Inc.	2009-07-06	Not applicable	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	North Star Rx Llc	2009-08-28	Not applicable	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Teva	2009-07-06	Not applicable	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Synthon Pharmaceuticals, Inc.	2009-07-06	Not applicable	US
Bicalutamide	Tablet	50 mg/1	Oral	Amerincan Health Packaging	2012-11-29	2016-09-30	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Mylan Pharmaceuticals	2009-07-06	Not applicable	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Breckenridge Pharmaceutical, Inc.	2010-11-16	Not applicable	US
Bicalutamide	Tablet	50 mg/1	Oral	Sandoz	2009-07-06	2017-12-31	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Golden State Medical Supply	2010-11-16	Not applicable	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Avera Mc Kennan Hospital	2015-03-01	Not applicable	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Av Kare, Inc.	2014-01-13	Not applicable	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Golden State Medical Supply	2014-05-08	Not applicable	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Cadila Pharnmaceuticals	2009-07-06	Not applicable	US
Bicalutamide	Tablet	50 mg/1	Oral	Major	2010-05-11	Not applicable	US
Bicalutamide	Tablet	50 mg/1	Oral	Remedy Repack	2013-09-19	2016-04-05	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Sun Pharma Global Inc.	2009-07-07	2017-07-31	US
Bicalutamide	Tablet	50 mg/1	Oral	Apotex Corporation	2009-07-06	Not applicable	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Sun Pharma Global FZE	2014-12-15	Not applicable	US
Bicalutamide	Tablet	50 mg/1	Oral	bryant ranch prepack	2009-07-06	Not applicable	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	DAVA Pharmaceuticals, Inc.	2009-07-06	Not applicable	US
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Physicians Total Care, Inc.	2010-08-09	Not applicable	US
Bicalutamide	Tablet	50 mg/1	Oral	Accord Healthcare Limited	2009-07-06	Not applicable	US

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Not Available

Brand mixtures

Not Available

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

Stage D2 Prostatic carcinoma

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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Androgen receptor	Protein	yes	antagonist	Human	P10275	details

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

Drug	Interaction	Drug group
Acenocoumarol	The serum concentration of Acenocoumarol can be increased when it is combined with Bicalutamide.	Approved
Acetyldigitoxin	Acetyldigitoxin may decrease the cardiotoxic activities of Bicalutamide.	Approved
Amiodarone	The metabolism of Bicalutamide can be decreased when combined with Amiodarone.	Approved, Investigational
Aprepitant	The serum concentration of Bicalutamide can be increased when it is combined with Aprepitant.	Approved, Investigational
Aripiprazole	The serum concentration of Aripiprazole can be increased when it is combined with Bicalutamide.	Approved, Investigational
Astemizole	The serum concentration of Astemizole can be increased when it is combined with Bicalutamide.	Approved, Withdrawn
Atazanavir	The metabolism of Bicalutamide can be decreased when combined with Atazanavir.	Approved, Investigational
Atomoxetine	The metabolism of Bicalutamide can be decreased when combined with Atomoxetine.	Approved
Bevacizumab	Bevacizumab may increase the cardiotoxic activities of Bicalutamide.	Approved, Investigational
Bexarotene	The serum concentration of Bicalutamide can be decreased when it is combined with Bexarotene.	Approved, Investigational
Boceprevir	The metabolism of Bicalutamide can be decreased when combined with Boceprevir.	Approved, Investigational
Bortezomib	The metabolism of Bicalutamide can be decreased when combined with Bortezomib.	Approved, Investigational
Bosentan	The serum concentration of Bicalutamide can be decreased when it is combined with Bosentan.	Approved, Investigational
Cabazitaxel	The risk or severity of adverse effects can be increased when Cabazitaxel is combined with Bicalutamide.	Approved
Carbamazepine	The metabolism of Bicalutamide can be increased when combined with Carbamazepine.	Approved, Investigational
Ceritinib	The serum concentration of Bicalutamide can be increased when it is combined with Ceritinib.	Approved
Choline C 11	The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Bicalutamide.	Approved
Cilostazol	The serum concentration of Cilostazol can be increased when it is combined with Bicalutamide.	Approved
Cisapride	The serum concentration of Cisapride can be increased when it is combined with Bicalutamide.	Approved, Investigational, Withdrawn
Clarithromycin	The metabolism of Bicalutamide can be decreased when combined with Clarithromycin.	Approved
Clemastine	The metabolism of Bicalutamide can be decreased when combined with Clemastine.	Approved
Clotrimazole	The metabolism of Bicalutamide can be decreased when combined with Clotrimazole.	Approved, Vet Approved
Cobicistat	The metabolism of Bicalutamide can be decreased when combined with Cobicistat.	Approved
Conivaptan	The serum concentration of Bicalutamide can be increased when it is combined with Conivaptan.	Approved, Investigational
Crizotinib	The metabolism of Bicalutamide can be decreased when combined with Crizotinib.	Approved
Cyclophosphamide	Cyclophosphamide may increase the cardiotoxic activities of Bicalutamide.	Approved, Investigational
Cyclosporine	The metabolism of Bicalutamide can be decreased when combined with Cyclosporine.	Approved, Investigational, Vet Approved
Dabrafenib	The serum concentration of Bicalutamide can be decreased when it is combined with Dabrafenib.	Approved
Darunavir	The metabolism of Bicalutamide can be decreased when combined with Darunavir.	Approved
Dasatinib	The serum concentration of Bicalutamide can be increased when it is combined with Dasatinib.	Approved, Investigational
Deferasirox	The serum concentration of Bicalutamide can be decreased when it is combined with Deferasirox.	Approved, Investigational
Delavirdine	The metabolism of Bicalutamide can be decreased when combined with Delavirdine.	Approved
Deslanoside	Deslanoside may decrease the cardiotoxic activities of Bicalutamide.	Approved
Dexamethasone	The serum concentration of Bicalutamide can be decreased when it is combined with Dexamethasone.	Approved, Investigational, Vet Approved
Dicoumarol	The serum concentration of Dicoumarol can be increased when it is combined with Bicalutamide.	Approved
Digitoxin	Digitoxin may decrease the cardiotoxic activities of Bicalutamide.	Approved
Digoxin	Digoxin may decrease the cardiotoxic activities of Bicalutamide.	Approved
Dihydroergotamine	The metabolism of Bicalutamide can be decreased when combined with Dihydroergotamine.	Approved
Diltiazem	The metabolism of Bicalutamide can be decreased when combined with Diltiazem.	Approved
Docetaxel	The risk or severity of adverse effects can be increased when Docetaxel is combined with Bicalutamide.	Approved, Investigational
Dofetilide	The serum concentration of Dofetilide can be increased when it is combined with Bicalutamide.	Approved
Doxycycline	The metabolism of Bicalutamide can be decreased when combined with Doxycycline.	Approved, Investigational, Vet Approved
Dronedarone	The metabolism of Bicalutamide can be decreased when combined with Dronedarone.	Approved
Efavirenz	The serum concentration of Bicalutamide can be decreased when it is combined with Efavirenz.	Approved, Investigational
Enzalutamide	The serum concentration of Bicalutamide can be decreased when it is combined with Enzalutamide.	Approved
Erythromycin	The metabolism of Bicalutamide can be decreased when combined with Erythromycin.	Approved, Vet Approved
Eslicarbazepine acetate	The serum concentration of Bicalutamide can be decreased when it is combined with Eslicarbazepine acetate.	Approved
Ethyl biscoumacetate	The serum concentration of Ethyl biscoumacetate can be increased when it is combined with Bicalutamide.	Withdrawn
Etravirine	The serum concentration of Bicalutamide can be decreased when it is combined with Etravirine.	Approved
Fesoterodine	The serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Bicalutamide.	Approved
Flibanserin	The serum concentration of Flibanserin can be increased when it is combined with Bicalutamide.	Approved
Fluconazole	The metabolism of Bicalutamide can be decreased when combined with Fluconazole.	Approved
Fluindione	The serum concentration of Fluindione can be increased when it is combined with Bicalutamide.	Investigational
Fluvoxamine	The metabolism of Bicalutamide can be decreased when combined with Fluvoxamine.	Approved, Investigational
Fosamprenavir	The metabolism of Bicalutamide can be decreased when combined with Fosamprenavir.	Approved
Fosaprepitant	The serum concentration of Bicalutamide can be increased when it is combined with Fosaprepitant.	Approved
Fosphenytoin	The metabolism of Bicalutamide can be increased when combined with Fosphenytoin.	Approved
Fusidic Acid	The serum concentration of Bicalutamide can be increased when it is combined with Fusidic Acid.	Approved
Hydrocodone	The serum concentration of Hydrocodone can be increased when it is combined with Bicalutamide.	Approved, Illicit
Idelalisib	The serum concentration of Bicalutamide can be increased when it is combined with Idelalisib.	Approved
Imatinib	The metabolism of Bicalutamide can be decreased when combined with Imatinib.	Approved
Indinavir	The metabolism of Bicalutamide can be decreased when combined with Indinavir.	Approved
Isavuconazonium	The metabolism of Bicalutamide can be decreased when combined with Isavuconazonium.	Approved, Investigational
Isradipine	The metabolism of Bicalutamide can be decreased when combined with Isradipine.	Approved
Itraconazole	The metabolism of Bicalutamide can be decreased when combined with Itraconazole.	Approved, Investigational
Ivacaftor	The serum concentration of Bicalutamide can be increased when it is combined with Ivacaftor.	Approved
Ketoconazole	The metabolism of Bicalutamide can be decreased when combined with Ketoconazole.	Approved, Investigational
Lomitapide	The serum concentration of Lomitapide can be increased when it is combined with Bicalutamide.	Approved
Lopinavir	The metabolism of Bicalutamide can be decreased when combined with Lopinavir.	Approved
Lovastatin	The metabolism of Bicalutamide can be decreased when combined with Lovastatin.	Approved, Investigational
Luliconazole	The serum concentration of Bicalutamide can be increased when it is combined with Luliconazole.	Approved
Lumacaftor	The metabolism of Bicalutamide can be increased when combined with Lumacaftor.	Approved
Metoprolol	The serum concentration of Metoprolol can be increased when it is combined with Bicalutamide.	Approved, Investigational
Mifepristone	The serum concentration of Bicalutamide can be increased when it is combined with Mifepristone.	Approved, Investigational
Mitotane	The serum concentration of Bicalutamide can be decreased when it is combined with Mitotane.	Approved
Modafinil	The serum concentration of Bicalutamide can be decreased when it is combined with Modafinil.	Approved, Investigational
Nafcillin	The serum concentration of Bicalutamide can be decreased when it is combined with Nafcillin.	Approved
Nefazodone	The metabolism of Bicalutamide can be decreased when combined with Nefazodone.	Approved, Withdrawn
Nelfinavir	The metabolism of Bicalutamide can be decreased when combined with Nelfinavir.	Approved
Netupitant	The serum concentration of Bicalutamide can be increased when it is combined with Netupitant.	Approved
Nevirapine	The metabolism of Bicalutamide can be increased when combined with Nevirapine.	Approved
Nilotinib	The metabolism of Bicalutamide can be decreased when combined with Nilotinib.	Approved, Investigational
Nimodipine	The serum concentration of Nimodipine can be increased when it is combined with Bicalutamide.	Approved
Olaparib	The metabolism of Bicalutamide can be decreased when combined with Olaparib.	Approved
Oleandrin	Anvirzel may decrease the cardiotoxic activities of Bicalutamide.	Experimental
Osimertinib	The serum concentration of Bicalutamide can be increased when it is combined with Osimertinib.	Approved
Ouabain	Ouabain may decrease the cardiotoxic activities of Bicalutamide.	Approved
Paclitaxel	The risk or severity of adverse effects can be increased when Paclitaxel is combined with Bicalutamide.	Approved, Vet Approved
Palbociclib	The serum concentration of Bicalutamide can be increased when it is combined with Palbociclib.	Approved
Pentobarbital	The metabolism of Bicalutamide can be increased when combined with Pentobarbital.	Approved, Vet Approved
Phenindione	The serum concentration of Phenindione can be increased when it is combined with Bicalutamide.	Approved
Phenobarbital	The metabolism of Bicalutamide can be increased when combined with Phenobarbital.	Approved
Phenprocoumon	The serum concentration of Phenprocoumon can be increased when it is combined with Bicalutamide.	Approved
Phenytoin	The metabolism of Bicalutamide can be increased when combined with Phenytoin.	Approved, Vet Approved
Pimozide	The serum concentration of Pimozide can be increased when it is combined with Bicalutamide.	Approved
Posaconazole	The metabolism of Bicalutamide can be decreased when combined with Posaconazole.	Approved, Investigational, Vet Approved
Primidone	The metabolism of Bicalutamide can be increased when combined with Primidone.	Approved, Vet Approved
Ranolazine	The metabolism of Bicalutamide can be decreased when combined with Ranolazine.	Approved, Investigational
Rifabutin	The metabolism of Bicalutamide can be increased when combined with Rifabutin.	Approved
Rifampicin	The metabolism of Bicalutamide can be increased when combined with Rifampicin.	Approved
Rifapentine	The metabolism of Bicalutamide can be increased when combined with Rifapentine.	Approved
Ritonavir	The metabolism of Bicalutamide can be decreased when combined with Ritonavir.	Approved, Investigational
Saquinavir	The metabolism of Bicalutamide can be decreased when combined with Saquinavir.	Approved, Investigational
Sildenafil	The metabolism of Bicalutamide can be decreased when combined with Sildenafil.	Approved, Investigational
Siltuximab	The serum concentration of Bicalutamide can be decreased when it is combined with Siltuximab.	Approved
Simeprevir	The serum concentration of Bicalutamide can be increased when it is combined with Simeprevir.	Approved
St. John's Wort	The serum concentration of Bicalutamide can be decreased when it is combined with St. John's Wort.	Nutraceutical
Stiripentol	The serum concentration of Bicalutamide can be increased when it is combined with Stiripentol.	Approved
Sulfisoxazole	The metabolism of Bicalutamide can be decreased when combined with Sulfisoxazole.	Approved, Vet Approved
Telaprevir	The metabolism of Bicalutamide can be decreased when combined with Telaprevir.	Withdrawn
Telithromycin	The metabolism of Bicalutamide can be decreased when combined with Telithromycin.	Approved
Terfenadine	The serum concentration of Terfenadine can be increased when it is combined with Bicalutamide.	Withdrawn
Thioridazine	The serum concentration of Thioridazine can be increased when it is combined with Bicalutamide.	Withdrawn
Ticlopidine	The metabolism of Bicalutamide can be decreased when combined with Ticlopidine.	Approved
Tocilizumab	The serum concentration of Bicalutamide can be decreased when it is combined with Tocilizumab.	Approved
Trastuzumab	Trastuzumab may increase the cardiotoxic activities of Bicalutamide.	Approved, Investigational
Venlafaxine	The metabolism of Bicalutamide can be decreased when combined with Venlafaxine.	Approved
Verapamil	The metabolism of Bicalutamide can be decreased when combined with Verapamil.	Approved
Voriconazole	The metabolism of Bicalutamide can be decreased when combined with Voriconazole.	Approved, Investigational
Warfarin	The serum concentration of Warfarin can be increased when it is combined with Bicalutamide.	Approved
Ziprasidone	The 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

Resource	Link
Human Metabolome Database (HMDB)	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	2863
Drug Product Database	141
RxList	http://www.rxlist.com/cgi/generic3/bicalutamide.htm
Drugs.com	http://www.drugs.com/cdi/bicalutamide.html
Wikipedia	Bicalutamide

ATC Codes

L02BB03 — Bicalutamide

AHFS Codes

10:00.00

PDB Entries

Not Available

FDA label

Download (182 KB)

MSDS

Download (57.3 KB)

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Completed	Treatment	Adenocarcinoma of the Prostate / Hormone-Resistant Prostate Cancer / Malignant Neoplasm of Prostate / Stage IV Prostate Cancer	1
1	Active Not Recruiting	Treatment	Malignant Neoplasm of Prostate	2
1	Completed	Not Available	Healthy Volunteers	2
1	Completed	Prevention	Healthy Volunteers	1
1	Completed	Treatment	Healthy Volunteers	2
1	Completed	Treatment	Malignant Neoplasm of Prostate	5
1	Terminated	Treatment	Adenocarcinoma of the Prostate / Recurrent Prostate Cancer	1
1	Terminated	Treatment	Healthy Volunteers	2
1	Terminated	Treatment	Malignant Neoplasm of Prostate	1
1	Terminated	Treatment	Non Castrate Metastatic Prostate Cancer	1
1, 2	Active Not Recruiting	Treatment	Malignant Neoplasm of Prostate	1
1, 2	Completed	Treatment	Malignant Neoplasm of Prostate / Prostatic Neoplasms	1
1, 2	Completed	Treatment	Prostatic Neoplasms	1
1, 2	Recruiting	Treatment	Adenocarcinoma, Prostate / Stage I Prostate Cancer / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer / Stage III Prostate Cancer	1
1, 2	Recruiting	Treatment	Metastatic Breast Cancer (MBC)	1
1, 2	Recruiting	Treatment	Triple Negative Breast Cancer (TNBC)	1
1, 2	Terminated	Treatment	Androgen-insensitive Prostate Cancer / Castrate-resistant Prostate Cancer (CRPC) / Hormone-Refractory Prostate Cancer / Malignant Neoplasm of Prostate / Metastatic Disease / Prostatic Neoplasms	1
1, 2	Terminated	Treatment	Malignant Neoplasm of Prostate	1
2	Active Not Recruiting	Treatment	Adenocarcinoma, Prostate / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer	1
2	Active Not Recruiting	Treatment	Cancer, Breast	1
2	Active Not Recruiting	Treatment	Erectile Dysfunction (ED) / Lower Urinary Tract Symptoms (LUTS) / Malignant Neoplasm of Prostate	1
2	Active Not Recruiting	Treatment	Hormone-Resistant Prostate Cancer / Recurrent Prostate Carcinoma	1
2	Active Not Recruiting	Treatment	Malignant Neoplasm of Prostate	5
2	Active Not Recruiting	Treatment	Prostatic Neoplasms	1
2	Active Not Recruiting	Treatment	Puberty, Precocious	1
2	Active Not Recruiting	Treatment	Recurrent Prostate Carcinoma / Stage I Prostate Cancer / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer / Stage III Prostate Cancer	1
2	Completed	Treatment	Adenocarcinoma of the Prostate / Malignant Neoplasm of Prostate	1
2	Completed	Treatment	Adenocarcinoma of the Prostate / Stage IV Prostate Cancer	1
2	Completed	Treatment	Adenocarcinoma, Prostate / Stage I Prostate Cancer / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer / Stage III Prostate Cancer	1
2	Completed	Treatment	Cancer, Ovarian / Fallopian Tube Cancer / Primary Peritoneal Cavity Cancer	1
2	Completed	Treatment	Cancers / Hormonal Cycling / Prostate	1
2	Completed	Treatment	Gynaecomastia / Malignant Neoplasm of Prostate	1
2	Completed	Treatment	Malignant Neoplasm of Prostate	15
2	Completed	Treatment	Recurrent Prostate Carcinoma / Stage I Prostate Cancer / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer / Stage III Prostate Cancer	1
2	Not Yet Recruiting	Treatment	Malignant Neoplasm of Prostate	1
2	Not Yet Recruiting	Treatment	Neoplasms, Breast	1
2	Recruiting	Treatment	Adenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage IV Prostate Cancer	1
2	Recruiting	Treatment	Bone Metastases / Malignant Neoplasm of Prostate / Prostate Neoplasms	1
2	Recruiting	Treatment	Cancer, Breast	2
2	Recruiting	Treatment	Malignant Neoplasm of Prostate	4
2	Recruiting	Treatment	Metastatic Breast Cancer (MBC)	1
2	Recruiting	Treatment	Salivary Gland Cancers	1
2	Recruiting	Treatment	Stage I Prostate Adenocarcinoma / Stage II Prostate Adenocarcinoma	1
2	Terminated	Treatment	Adenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage IV Prostate Cancer	1
2	Terminated	Treatment	Cancer, Breast	1
2	Terminated	Treatment	Malignant Neoplasm of Prostate	2
2	Terminated	Treatment	Prostatic Neoplasms	1
2	Unknown Status	Treatment	Malignant Neoplasm of Prostate	1
2	Withdrawn	Not Available	Malignant Neoplasm of Prostate	1
2	Withdrawn	Treatment	Adenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage III Prostate Cancer / Stage IV Prostate Cancer	1
2	Withdrawn	Treatment	Malignant Neoplasm of Prostate	4
2, 3	Completed	Not Available	Malignant Neoplasm of Prostate	1
2, 3	Recruiting	Treatment	Stage I Prostate Adenocarcinoma / Stage II Prostate Adenocarcinoma / Stage III Prostate Adenocarcinoma	1
3	Active Not Recruiting	Treatment	Malignant Neoplasm of Prostate	6
3	Completed	Health Services Research	Malignant Neoplasm of Prostate	1
3	Completed	Prevention	Malignant Neoplasm of Prostate	1
3	Completed	Treatment	Malignant Neoplasm of Prostate	14
3	Completed	Treatment	Non-Metastatic Prostate Cancer	3
3	Recruiting	Prevention	Metastatic Triple Negative Breast Cancer	1
3	Recruiting	Treatment	Malignant Neoplasm of Prostate	1
3	Recruiting	Treatment	Prostatic Neoplasms	1
3	Terminated	Treatment	Malignant Neoplasm of Prostate	6
3	Terminated	Treatment	Prostatic Neoplasms	1
3	Unknown Status	Treatment	Gastrointestinal Complications / Malignant Neoplasm of Prostate / Sexual Dysfunctions / Urinary Complications	1
3	Unknown Status	Treatment	Malignant Neoplasm of Prostate	2
4	Completed	Treatment	Malignant Neoplasm of Prostate	1
4	Completed	Treatment	Prostate Neoplasms	1
4	Withdrawn	Treatment	Metastatic Hormone Refractory Prostate Cancer	1
Not Available	Active Not Recruiting	Not Available	Malignant Neoplasm of Prostate	1
Not Available	Active Not Recruiting	Treatment	Stage III Prostate Cancer	1
Not Available	Completed	Prevention	Bone destruction	1
Not Available	Completed	Treatment	Prostatic Neoplasms	1
Not Available	No Longer Available	Not Available	Adenocarcinoma of the Prostate	1
Not Available	Not Yet Recruiting	Treatment	Stage IV Prostate Cancer	1
Not Available	Recruiting	Not Available	Malignant Neoplasm of Prostate	1
Not Available	Recruiting	Treatment	Adenocarcinoma of the Prostate	1
Not Available	Recruiting	Treatment	Malignant Neoplasm of Prostate	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Dosage forms

Form	Route	Strength
Tablet	Oral	50 mg/1
Tablet, film coated	Oral	50 mg/1
Tablet	Oral	50 mg

Prices

Unit description	Cost	Unit
Casodex 50 mg tablet	20.19USD	tablet
Bicalutamide 50 mg tablet	18.92USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	191-193 °C	Not Available
water solubility	5 mg/L	Not Available
logP	2.5	Not Available
pKa	12.0	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00928 mg/mL	ALOGPS
logP	2.7	ALOGPS
logP	2.71	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	11.95	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	107.26 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	96.59 m³·mol^-1	ChemAxon
Polarizability	36.68 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9471
Blood Brain Barrier	+	0.859
Caco-2 permeable	-	0.6085
P-glycoprotein substrate	Non-substrate	0.6741
P-glycoprotein inhibitor I	Non-inhibitor	0.7171
P-glycoprotein inhibitor II	Non-inhibitor	0.9178
Renal organic cation transporter	Non-inhibitor	0.9572
CYP450 2C9 substrate	Non-substrate	0.6883
CYP450 2D6 substrate	Non-substrate	0.8087
CYP450 3A4 substrate	Non-substrate	0.5536
CYP450 1A2 substrate	Non-inhibitor	0.8513
CYP450 2C9 inhibitor	Non-inhibitor	0.6246
CYP450 2D6 inhibitor	Non-inhibitor	0.8683
CYP450 2C19 inhibitor	Inhibitor	0.7976
CYP450 3A4 inhibitor	Inhibitor	0.7879
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.5662
Ames test	Non AMES toxic	0.7134
Carcinogenicity	Non-carcinogens	0.6067
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.4383 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9959
hERG inhibition (predictor II)	Non-inhibitor	0.8759

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014r-2950100000-4088c17274bcf0f095d4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014r-0980100000-89a3faa58e22068394b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

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

Substituents

Trifluoromethylbenzene / Benzenesulfonyl group / Anilide / Benzonitrile / N-arylamide / Fluorobenzene / Halobenzene / Aryl fluoride / Aryl halide / Tertiary alcohol

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 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

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 ]
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 ]
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 ]
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 ]
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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Details

1. Cytochrome P450 3A4

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

Cockshott ID: Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78. [PubMed:15509184 ]

Details

2. Cytochrome P450 2C19

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

Cockshott ID: Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78. [PubMed:15509184 ]

Details

3. Cytochrome P450 2C9

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

Cockshott ID: Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78. [PubMed:15509184 ]

Details

4. Cytochrome P450 2D6

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

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 July 18, 2017 16:56

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Structure for DB01128 (Bicalutamide)

Targets

References

Enzymes

References

References

References

References