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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyBicalutamide
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
Structure for DB01128 (Bicalutamide)
- Synonyms
- Bicalutamida
- Bicalutamide
- Bicalutamidum
- External IDs
- ICI 176,334 / ICI-176334 / ICI176,334-1
- Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Act Bicalutamide Tablet 50 mg Oral Actavis Pharma Company 2006-02-07 Not applicable 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 Oral Astra Zeneca 1996-12-31 Not applicable Canada Casodex Tablet 50 mg/1 Oral Astra Zeneca Lp 1995-10-16 Not applicable US Sandoz Bicalutamide Tablet 50 mg Oral Sandoz Canada Incorporated 2006-02-08 Not applicable Canada - Generic 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 Ag-bicalutamide Tablet 50 mg Oral Angita Pharma Inc. Not applicable Not applicable Canada Apo-bicalutamide Tablet 50 mg Oral Apotex Corporation 2007-11-05 Not applicable Canada Ava-bicalutamide Tablet 50 mg Oral Avanstra Inc 2011-11-23 2014-08-21 Canada Bicalutamide Tablet, film coated 50 mg/1 Oral Cadila Pharnmaceuticals 2009-07-06 Not applicable US Bicalutamide Tablet, film coated 50 mg/1 Oral Mylan Pharmaceuticals 2009-07-06 2018-01-16 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 2010-11-16 2017-10-26 US Bicalutamide Tablet, film coated 50 mg/1 Oral Breckenridge Pharmaceutical, Inc. 2010-11-16 2017-09-20 US - Categories
- Amides
- Androgen Antagonists
- Androgen Receptor Inhibitor
- Antiandrogens
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Benzene Derivatives
- Cytochrome P-450 Enzyme Inhibitors
- Endocrine Therapy
- Hormone Antagonists
- Hormone Antagonists and Related Agents
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Non-Steroidal Anti-Androgens
- P-glycoprotein/ABCB1 Inhibitors
- Sulfones
- Sulfur Compounds
- Toluene
- 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.
- Associated Conditions
- 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 Actions Organism AAndrogen receptor antagonistHuman - 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, Investigational Acetyl sulfisoxazole The metabolism of Bicalutamide can be decreased when combined with Acetyl sulfisoxazole. Approved, Vet Approved Acetyldigitoxin Acetyldigitoxin may decrease the cardiotoxic activities of Bicalutamide. Approved Acetyldigoxin Acetyldigoxin may decrease the cardiotoxic activities of Bicalutamide. Experimental Amiodarone The metabolism of Bicalutamide can be decreased when combined with Amiodarone. Approved, Investigational Ancestim The risk or severity of cytotoxicity can be increased when Ancestim is combined with Bicalutamide. Approved, Investigational, Withdrawn Apalutamide The serum concentration of Bicalutamide can be decreased when it is combined with Apalutamide. Approved, Investigational Aprepitant The serum concentration of Bicalutamide can be increased when it is combined with Aprepitant. Approved, Investigational Astemizole The serum concentration of Astemizole can be increased when it is combined with Bicalutamide. Approved, Withdrawn Asunaprevir The serum concentration of Asunaprevir can be increased when it is combined with Bicalutamide. Approved, Investigational, 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 Atorvastatin The risk or severity of adverse effects can be increased when Bicalutamide is combined with Atorvastatin. Approved Bevacizumab Bevacizumab may increase the cardiotoxic activities of Bicalutamide. Approved, Investigational Boceprevir The metabolism of Bicalutamide can be decreased when combined with Boceprevir. Approved, Withdrawn 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 Bosutinib The serum concentration of Bosutinib can be increased when it is combined with Bicalutamide. Approved Bromocriptine The risk or severity of adverse effects can be increased when Bromocriptine is combined with Bicalutamide. Approved, Investigational Cabazitaxel The risk or severity of adverse effects can be increased when Cabazitaxel is combined with Bicalutamide. Approved Cabergoline The risk or severity of adverse effects can be increased when Cabergoline is combined with Bicalutamide. Approved Capromab pendetide Bicalutamide may decrease effectiveness of Capromab pendetide as a diagnostic agent. 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 Cerivastatin The serum concentration of Cerivastatin can be increased when it is combined with Bicalutamide. Approved, Withdrawn Choline C 11 The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Bicalutamide. Approved, Investigational Cilostazol The serum concentration of Cilostazol can be increased when it is combined with Bicalutamide. Approved, Investigational 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, Investigational Clorindione The serum concentration of Clorindione can be increased when it is combined with Bicalutamide. Experimental 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 Conivaptan can be increased when it is combined with Bicalutamide. Approved, Investigational Crizotinib The metabolism of Bicalutamide can be decreased when combined with Crizotinib. Approved Curcumin The metabolism of Bicalutamide can be decreased when combined with Curcumin. Approved, Investigational 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 Cymarin Cymarin may decrease the cardiotoxic activities of Bicalutamide. Experimental Dabrafenib The serum concentration of Bicalutamide can be decreased when it is combined with Dabrafenib. Approved, Investigational 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 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, Investigational Digoxin Digoxin may decrease the cardiotoxic activities of Bicalutamide. Approved Digoxin Immune Fab (Ovine) Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Bicalutamide. Approved Dihydroergocornine The risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Bicalutamide. Approved Dihydroergocristine The risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Bicalutamide. Approved, Experimental Dihydroergocryptine The risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Bicalutamide. Experimental Dihydroergotamine The risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Bicalutamide. Approved, Investigational Diltiazem The metabolism of Bicalutamide can be decreased when combined with Diltiazem. Approved, Investigational Diphenadione The serum concentration of Diphenadione can be increased when it is combined with Bicalutamide. Experimental Docetaxel The risk or severity of adverse effects can be increased when Docetaxel is combined with Bicalutamide. Approved, Investigational 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 Enzalutamide The serum concentration of Bicalutamide can be decreased when it is combined with Enzalutamide. Approved Ergonovine The risk or severity of adverse effects can be increased when Ergonovine is combined with Bicalutamide. Approved Ergotamine The risk or severity of adverse effects can be increased when Ergotamine is combined with Bicalutamide. Approved Erythromycin The metabolism of Bicalutamide can be decreased when combined with Erythromycin. Approved, Investigational, Vet Approved Ethyl biscoumacetate The serum concentration of Ethyl biscoumacetate can be increased when it is combined with Bicalutamide. Withdrawn Fesoterodine The serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Bicalutamide. Approved Fluconazole The metabolism of Bicalutamide can be decreased when combined with Fluconazole. Approved, Investigational Fluindione The serum concentration of Fluindione can be increased when it is combined with Bicalutamide. Approved, Investigational Fluvastatin The serum concentration of Fluvastatin can be increased when it is combined with Bicalutamide. Approved 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, Investigational Fusidic Acid The serum concentration of Bicalutamide can be increased when it is combined with Fusidic Acid. Approved, Investigational Gitoformate Gitoformate may decrease the cardiotoxic activities of Bicalutamide. Experimental Ibrutinib The serum concentration of Ibrutinib can be increased when it is combined with Bicalutamide. Approved Idelalisib The metabolism of Bicalutamide can be decreased when 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 Isavuconazole The serum concentration of Bicalutamide can be increased when it is combined with Isavuconazole. Approved, Investigational 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, Investigational 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 Lanatoside C Lanatoside C may decrease the cardiotoxic activities of Bicalutamide. Experimental Lisuride The risk or severity of adverse effects can be increased when Lisuride is combined with Bicalutamide. Approved, Investigational Lopinavir The metabolism of Bicalutamide can be decreased when combined with Lopinavir. Approved Lorpiprazole The serum concentration of Bicalutamide can be increased when it is combined with Lorpiprazole. Approved Lovastatin The serum concentration of Lovastatin can be increased when it is combined with Bicalutamide. 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 Lysergic Acid Diethylamide The risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Bicalutamide. Illicit, Investigational, Withdrawn Metergoline The risk or severity of adverse effects can be increased when Metergoline is combined with Bicalutamide. Experimental Methylergometrine The risk or severity of adverse effects can be increased when Methylergometrine is combined with Bicalutamide. Approved Methysergide The risk or severity of adverse effects can be increased when Methysergide is combined with Bicalutamide. Approved Metildigoxin Metildigoxin may decrease the cardiotoxic activities of Bicalutamide. Experimental Metoprolol The serum concentration of Metoprolol can be increased when it is combined with Bicalutamide. Approved, Investigational Mevastatin The serum concentration of Mevastatin can be increased when it is combined with Bicalutamide. Experimental 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 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, Investigational Nevirapine The metabolism of Bicalutamide can be increased when combined with Nevirapine. Approved Nicergoline The risk or severity of adverse effects can be increased when Nicergoline is combined with Bicalutamide. Approved, Investigational Nilotinib The metabolism of Bicalutamide can be decreased when combined with Nilotinib. Approved, Investigational Olaparib The metabolism of Bicalutamide can be decreased when combined with Olaparib. Approved Oleandrin Oleandrin may decrease the cardiotoxic activities of Bicalutamide. Experimental, Investigational 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, Investigational Pentobarbital The metabolism of Bicalutamide can be increased when combined with Pentobarbital. Approved, Investigational, Vet Approved Pergolide The risk or severity of adverse effects can be increased when Pergolide is combined with Bicalutamide. Approved, Investigational, Vet Approved, Withdrawn Peruvoside Peruvoside may decrease the cardiotoxic activities of Bicalutamide. Experimental Phenindione The serum concentration of Phenindione can be increased when it is combined with Bicalutamide. Approved, Investigational Phenobarbital The metabolism of Bicalutamide can be increased when combined with Phenobarbital. Approved, Investigational Phenprocoumon The serum concentration of Phenprocoumon can be increased when it is combined with Bicalutamide. Approved, Investigational Phenytoin The metabolism of Bicalutamide can be increased when combined with Phenytoin. Approved, Vet Approved Pitavastatin The serum concentration of Pitavastatin can be increased when it is combined with Bicalutamide. Approved Pitolisant The serum concentration of Pitolisant can be increased when it is combined with Bicalutamide. Approved, Investigational Posaconazole The metabolism of Bicalutamide can be decreased when combined with Posaconazole. Approved, Investigational, Vet Approved Pravastatin The serum concentration of Pravastatin can be increased when it is combined with Bicalutamide. Approved Primidone The metabolism of Bicalutamide can be increased when combined with Primidone. Approved, Vet Approved Proscillaridin Proscillaridin may decrease the cardiotoxic activities of Bicalutamide. Experimental 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, Investigational 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, Investigational Rilpivirine The serum concentration of Rilpivirine can be increased when it is combined with Bicalutamide. Approved Rosuvastatin The serum concentration of Rosuvastatin can be increased when it is combined with Bicalutamide. Approved Rucaparib The metabolism of Bicalutamide can be decreased when combined with Rucaparib. Approved, Investigational Saquinavir The metabolism of Bicalutamide can be decreased when combined with Saquinavir. Approved, Investigational Sarilumab The therapeutic efficacy of Bicalutamide can be decreased when used in combination with Sarilumab. 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, Investigational Simeprevir The serum concentration of Bicalutamide can be increased when it is combined with Simeprevir. Approved Simvastatin The serum concentration of Simvastatin can be increased when it is combined with Bicalutamide. Approved St. John's Wort The serum concentration of Bicalutamide can be decreased when it is combined with St. John's Wort. Approved, Investigational, 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. Approved, 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. Approved, Withdrawn Terguride The risk or severity of adverse effects can be increased when Terguride is combined with Bicalutamide. Experimental Thioridazine The serum concentration of Thioridazine can be increased when it is combined with Bicalutamide. Approved, Withdrawn Ticlopidine The metabolism of Bicalutamide can be decreased when combined with Ticlopidine. Approved Tioclomarol The serum concentration of Tioclomarol can be increased when it is combined with Bicalutamide. Experimental Tocilizumab The serum concentration of Bicalutamide can be decreased when it is combined with Tocilizumab. Approved Tolvaptan The serum concentration of Tolvaptan can be increased when it is combined with Bicalutamide. Approved Trastuzumab Trastuzumab may increase the cardiotoxic activities of Bicalutamide. Approved, Investigational Vemurafenib The serum concentration of Bicalutamide can be decreased when it is combined with Vemurafenib. Approved 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
- Human Metabolome Database
- HMDB0015260
- 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
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Accord Healthcare
- Amerisource Health Services Corp.
- Apotex Inc.
- AstraZeneca Inc.
- Cadila Healthcare Ltd.
- DAVA Pharmaceuticals
- Intas Pharmaceuticals Ltd.
- Major Pharmaceuticals
- Mylan
- Sandoz
- Schwarz Pharma Inc.
- Sun Pharmaceutical Industries Ltd.
- Synthon Pharmaceuticals Inc.
- Teva Pharmaceutical Industries Ltd.
- UDL Laboratories
- Zydus Pharmaceuticals
- 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-0a4r-0890000000-f2bd2727ffd1da47c463 MS/MS Spectrum - , positive LC-MS/MS splash10-014r-2950100000-4088c17274bcf0f095d4 MS/MS Spectrum - , positive LC-MS/MS splash10-014r-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
- 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
- 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]
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Enzymes
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- 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
- 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
- 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
- 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 16, 2018 21:20