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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 Bicalutamide (DB01128)
- 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 Sivem Pharmaceuticals Ulc 2012-06-10 Not applicable Canada Bicalutamide Tablet 50 mg Oral Sorres Pharma Inc 2009-06-22 2014-06-20 Canada Bicalutamide Tablets Tablet 50 mg Oral Fresenius Kabi Not applicable Not applicable Canada Casodex Tablet 50 mg/1 Oral AstraZeneca Pharnaceuticals LP 2007-01-08 2007-01-08 US 
Casodex Tablet 50 mg/1 Oral ANI Pharmaceuticals, Inc. 2018-06-26 Not applicable US Casodex Tablet 50 mg Oral Astra Zeneca 1996-12-31 Not applicable Canada Casodex Tablet 50 mg/1 Oral AstraZeneca Pharmaceuticals LP 1995-10-16 2019-09-30 US Casodex Tablet 50 mg/1 Oral Physicians Total Care, Inc. 2002-06-04 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 50 mg/1 Oral Accord Healthcare Inc. 2009-07-06 Not applicable 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 Sandoz 2009-07-06 2017-12-31 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 Amerincan Health Packaging 2010-01-13 2013-08-31 US - Categories
- Amides
- Androgen Receptor Antagonists
- Androgen Receptor Inhibitor
- Antiandrogens
- Antiandrogens, non-steroidal
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Benzene Derivatives
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Endocrine Therapy
- Hormone Antagonists
- Hormone Antagonists and Related Agents
- Hormones, Hormone Substitutes, and Hormone Antagonists
- 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 (R)-warfarin The metabolism of (R)-warfarin can be decreased when combined with Bicalutamide. (S)-Warfarin The metabolism of (S)-Warfarin can be decreased when combined with Bicalutamide. 3,5-diiodothyropropionic acid The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Bicalutamide. 4-hydroxycoumarin The metabolism of 4-hydroxycoumarin can be decreased when combined with Bicalutamide. 4-Methoxyamphetamine The metabolism of 4-Methoxyamphetamine can be decreased when combined with Bicalutamide. 5-androstenedione The metabolism of 5-androstenedione can be decreased when combined with Bicalutamide. 6-Deoxyerythronolide B The metabolism of Bicalutamide can be decreased when combined with 6-Deoxyerythronolide B. 6-O-benzylguanine The metabolism of 6-O-benzylguanine can be decreased when combined with Bicalutamide. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Bicalutamide. Abiraterone The metabolism of Abiraterone can be decreased when combined with Bicalutamide. - 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, film coated Oral 50 mg/1 Tablet 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Enzymes
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation 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]
- Bicalutamide [Link]
- 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 November 20, 2018 00:51