Bicalutamide

Identification

Summary

Bicalutamide is an androgen receptor inhibitor used to treat Stage D2 metastatic carcinoma of the prostate.

Brand Names
Casodex
Generic Name
Bicalutamide
DrugBank Accession Number
DB01128
Background

Bicalutamide is an oral non-steroidal anti-androgen for prostate cancer. It is comprised of a racemic mixture that is a 50:50 composition of the (R)-bicalutamide and (S)-bicalutamide enantionmers. Bicalutamide binds to the androgen receptor.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 430.373
Monoisotopic: 430.061040456
Chemical Formula
C18H14F4N2O4S
Synonyms
  • Bicalutamida
  • Bicalutamide
  • Bicalutamidum
External IDs
  • ICI 176,334
  • ICI-176334
  • ICI176,334-1

Pharmacology

Indication

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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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
Humans
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]
Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Bicalutamide can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Bicalutamide can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Bicalutamide.
AbirateroneThe metabolism of Bicalutamide can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Bicalutamide.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Bicalutamide.
AcetaminophenThe metabolism of Acetaminophen can be increased when combined with Bicalutamide.
AcetazolamideThe metabolism of Bicalutamide can be decreased when combined with Acetazolamide.
AdalimumabThe metabolism of Bicalutamide can be increased when combined with Adalimumab.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Bicalutamide.
Interactions
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Food Interactions
  • Take at the same time every day.
  • Take with or without food. Food does not significantly affect absorption.

Products

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Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act BicalutamideTabletOralActavis Pharma Company2006-02-072018-07-11Canada flag
BicalutamideTablet50 mg/1OralANI Pharmaceuticals, Inc.2020-10-26Not applicableUS flag
BicalutamideTablet50 mgOralSivem Pharmaceuticals Ulc2012-06-102020-01-22Canada flag
BicalutamideTablet50 mgOralSorres Pharma Inc2009-06-222014-06-20Canada flag
Bicalutamide TabletsTabletOralFresenius KabiNot applicableNot applicableCanada flag
CasodexTablet50 mg/1OralAstraZeneca Pharmaceuticals LP1995-10-162019-09-30US flag
CasodexTablet50 mgOralAstra Zeneca1996-12-31Not applicableCanada flag
CasodexTablet50 mg/1OralAstraZeneca Pharnaceuticals LP2007-01-082007-01-08US flag
CasodexTablet50 mg/1OralANI Pharmaceuticals, Inc.2018-06-26Not applicableUS flag
CasodexTablet50 mg/1OralPhysicians Total Care, Inc.2002-06-04Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Accel-bicalutamide Tablets USPTabletOralAccel Pharma IncNot applicableNot applicableCanada flag
Ach-bicalutamideTabletOralAccord Healthcare Inc2010-05-05Not applicableCanada flag
Ag-bicalutamideTabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Apo-bicalutamideTabletOralApotex Corporation2007-11-05Not applicableCanada flag
Ava-bicalutamideTabletOralAvanstra Inc2011-11-232014-08-21Canada flag
BicalutamideTablet, film coated50 mg/1OralPhysicians Total Care, Inc.2010-08-09Not applicableUS flag54868 613320180907 15195 ees4h1
BicalutamideTablet50 mg/1Oralbryant ranch prepack2009-07-062018-09-30US flag63629 532120180907 15195 wd7dp0
BicalutamideTablet50 mg/1Oralbryant ranch prepack2009-07-06Not applicableUS flag
BicalutamideTablet, film coated50 mg/1OralMylan Pharmaceuticals2009-07-062014-03-31US flag
BicalutamideTablet, film coated50 mg/1OralBreckenridge Pharmaceutical, Inc.2010-11-162013-07-31US flag

Categories

ATC Codes
L02BB03 — BicalutamideL02AE51 — Leuprorelin and bicalutamide
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Alkyl fluoride / Alkyl halide / Anilide / Aromatic homomonocyclic compound / Aryl fluoride / Aryl halide / Benzenesulfonyl group / Benzonitrile / Carbonitrile
show 22 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
A0Z3NAU9DP
CAS number
90357-06-5
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

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
Human Metabolome Database
HMDB0015260
KEGG Drug
D00961
KEGG Compound
C08160
PubChem Compound
2375
PubChem Substance
46505386
ChemSpider
2284
BindingDB
18525
RxNav
83008
ChEBI
144093
ChEMBL
CHEMBL409
Therapeutic Targets Database
DAP000092
PharmGKB
PA164746255
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Bicalutamide
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
FDA label
Download (182 KB)
MSDS
Download (57.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentNeoplasms of the Prostate / Prostate Neoplasms1
4CompletedTreatmentProstate Cancer2
4RecruitingSupportive CareProstatic Neoplasms1
4RecruitingTreatmentAdvanced Prostate Cancer1
4WithdrawnTreatmentMetastatic Hormone Refractory Prostate Cancer1
3Active Not RecruitingTreatmentGastrointestinal Complications / Prostate Cancer / Sexual Dysfunctions / Urinary Complications1
3Active Not RecruitingTreatmentHormone-dependent prostate cancer / Prostate Cancer1
3Active Not RecruitingTreatmentProstate Cancer9
3Active Not RecruitingTreatmentProstatic Neoplasms1
3CompletedHealth Services ResearchProstate Cancer1

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
FormRouteStrength
Tablet, film coatedOral
Tablet, coatedOral
Tablet, film coatedOral50 mg/1
TabletOral
TabletOral50 mg/1
Tablet, film coatedOral150 mg
Tablet, coatedOral50 mg
Tablet, coatedOral150 mg
Tablet, film coatedOral50 mg
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

Targets

Drugtargets
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Details
1. Androgen receptor
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. [Article]
  2. Bicalutamide Labeling [File]
Kind
Protein
Organism
Humans
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. [Article]
  2. Bicalutamide [Link]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Zhu Y, Liu C, Armstrong C, Lou W, Sandher A, Gao AC: Antiandrogens Inhibit ABCB1 Efflux and ATPase Activity and Reverse Docetaxel Resistance in Advanced Prostate Cancer. Clin Cancer Res. 2015 Sep 15;21(18):4133-42. doi: 10.1158/1078-0432.CCR-15-0269. Epub 2015 May 20. [Article]

Drug created on June 13, 2005 13:24 / Updated on May 11, 2021 01:04