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.

Structure

Similar Structures

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
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Act Bicalutamide	Tablet	50 mg	Oral	Actavis Pharma Company	2006-02-07	Not applicable
Bicalutamide	Tablet	50 mg	Oral	Sivem Pharmaceuticals Ulc	2012-06-10	Not applicable
Bicalutamide	Tablet	50 mg	Oral	Sorres Pharma Inc	2009-06-22	2014-06-20
Bicalutamide Tablets	Tablet	50 mg	Oral	Fresenius Kabi	Not applicable	Not applicable
Casodex	Tablet	50 mg/1	Oral	AstraZeneca Pharmaceuticals LP	1995-10-16	2019-09-30
Casodex	Tablet	50 mg/1	Oral	AstraZeneca Pharnaceuticals LP	2007-01-08	2007-01-08
Casodex	Tablet	50 mg/1	Oral	ANI Pharmaceuticals, Inc.	2018-06-26	Not applicable
Casodex	Tablet	50 mg/1	Oral	Physicians Total Care, Inc.	2002-06-04	Not applicable
Casodex	Tablet	50 mg	Oral	Astra Zeneca	1996-12-31	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Accel-bicalutamide Tablets USP	Tablet	50 mg	Oral	Accel Pharma Inc	Not applicable	Not applicable
Ach-bicalutamide	Tablet	50 mg	Oral	Accord Healthcare Limited	2010-05-05	Not applicable
Ag-bicalutamide	Tablet	50 mg	Oral	Angita Pharma Inc.	Not applicable	Not applicable
Apo-bicalutamide	Tablet	50 mg	Oral	Apotex Corporation	2007-11-05	Not applicable
Ava-bicalutamide	Tablet	50 mg	Oral	Avanstra Inc	2011-11-23	2014-08-21
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Golden State Medical Supply, Inc.	2014-05-08	Not applicable
Bicalutamide	Tablet, film coated	50 mg/1	Oral	North Star Rx Llc	2018-06-01	Not applicable
Bicalutamide	Tablet, film coated	50 mg/1	Oral	Golden State Medical Supply	2010-11-16	2017-01-02
Bicalutamide	Tablet	50 mg/1	Oral	Sandoz	2009-07-06	2017-12-31
Bicalutamide	Tablet	50 mg/1	Oral	Apotex Corporation	2009-07-06	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

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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.

Associated Conditions

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	Actions	Organism
AAndrogen receptor	antagonist	Humans

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Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
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(R)-warfarin	The serum concentration of (R)-warfarin can be increased when it is combined with Bicalutamide.
(S)-Warfarin	The serum concentration of (S)-Warfarin can be increased when it is 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.
7-ethyl-10-hydroxycamptothecin	The metabolism of Bicalutamide can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
9-aminocamptothecin	The metabolism of 9-aminocamptothecin can be decreased when combined with Bicalutamide.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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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: 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

ATC Codes

L02BB03 — Bicalutamide

L02AE51 — Leuprorelin and bicalutamide

AHFS Codes

10:00.00 — Antineoplastic Agents

FDA label

Download (182 KB)

MSDS

Download (57.3 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Completed	Treatment	Adenocarcinoma of the Prostate / Hormone-Resistant Prostate Cancer / Prostate Cancer / Stage IV Prostate Cancer	1
0	Recruiting	Treatment	Prostate Cancer	1
1	Active Not Recruiting	Treatment	Prostate Cancer	2
1	Completed	Not Available	Healthy Volunteers	2
1	Completed	Prevention	Healthy Volunteers	1
1	Completed	Treatment	Healthy Volunteers	2
1	Completed	Treatment	Prostate Cancer	5
1	Terminated	Treatment	Adenocarcinoma of the Prostate / Recurrent Prostate Cancer	1
1	Terminated	Treatment	Healthy Volunteers	2
1	Terminated	Treatment	Non Castrate Metastatic Prostate Cancer	1
1	Terminated	Treatment	Prostate Cancer	1
1, 2	Active Not Recruiting	Treatment	Triple Negative Breast Cancer (TNBC)	1
1, 2	Completed	Treatment	Prostate Cancer	1
1, 2	Completed	Treatment	Prostate Cancer / 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	Terminated	Treatment	Androgen-insensitive Prostate Cancer / Castrate-resistant Prostate Cancer (CRPC) / Hormone-Refractory Prostate Cancer / Metastatic Disease / Prostate Cancer / Prostatic Neoplasms	1
1, 2	Terminated	Treatment	Prostate Cancer	1
2	Active Not Recruiting	Treatment	Adenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage IV Prostate Cancer	1
2	Active Not Recruiting	Treatment	Adenocarcinoma, Prostate / Prostate Cancer / PSA Level Greater Than or Equal to 0.2 / PSA Progression / Recurrent Prostate Carcinoma	1
2	Active Not Recruiting	Treatment	Cancer, Breast	2
2	Active Not Recruiting	Treatment	Erectile Dysfunction (ED) / Lower Urinary Tract Symptoms (LUTS) / Prostate Cancer	1
2	Active Not Recruiting	Treatment	Hormone-Resistant Prostate Cancer / Recurrent Prostate Carcinoma	1
2	Active Not Recruiting	Treatment	Prostate Cancer / PSA Level Greater Than Two / Stage IV Prostate Adenocarcinoma AJCC v7	1
2	Active Not Recruiting	Treatment	Prostate Cancer	2
2	Active Not Recruiting	Treatment	Recurrent Prostate Carcinoma / Stage I Prostate Cancer / Stage I Prostate Cancer AJCC v7 / Stage IIA Prostate Cancer / Stage IIA Prostate Cancer AJCC v7 / Stage IIB Prostate Cancer / Stage IIB Prostate Cancer AJCC v7 / Stage III Prostate Cancer / Stage III Prostate Cancer AJCC v7	1
2	Completed	Treatment	Adenocarcinoma of the Prostate / Prostate Cancer	1
2	Completed	Treatment	Adenocarcinoma of the Prostate / Stage IV Prostate Cancer	1
2	Completed	Treatment	Adenocarcinoma, Prostate / Recurrent Prostate Carcinoma / 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 of the Ovary / Fallopian Tube Cancer / Primary Peritoneal Cavity Cancer	1
2	Completed	Treatment	Gynaecomastia / Prostate Cancer	1
2	Completed	Treatment	Hormonal Cycling / Malignancies / Prostate	1
2	Completed	Treatment	Prostate Cancer	19
2	Completed	Treatment	Prostatic Neoplasms	1
2	Completed	Treatment	Puberty, Precocious	1
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	Neoplasms, Breast	1
2	Not Yet Recruiting	Treatment	Prostate Cancer	1
2	Recruiting	Treatment	Breast Neoplasm Female / Cancer, Breast / Carcinoma, Breast / Tumors, Breast	1
2	Recruiting	Treatment	Cancer, Breast	1
2	Recruiting	Treatment	High-risk Prostate Cancer / Prostate Cancer	1
2	Recruiting	Treatment	Metastatic Breast Cancer (MBC)	1
2	Recruiting	Treatment	Prostate Cancer	6
2	Recruiting	Treatment	Salivary Gland Cancers	1
2	Terminated	Treatment	Adenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage IV Prostate Cancer	1
2	Terminated	Treatment	Bone Metastases / Prostate Cancer / Prostate Neoplasms	1
2	Terminated	Treatment	Cancer, Breast	1
2	Terminated	Treatment	Prostate Cancer	1
2	Terminated	Treatment	Prostatic Neoplasms	1
2	Unknown Status	Treatment	Prostate Cancer	1
2	Withdrawn	Not Available	Prostate Cancer	1
2	Withdrawn	Treatment	Adenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage III Prostate Cancer / Stage IV Prostate Cancer	1
2	Withdrawn	Treatment	Prostate Cancer	4
2	Withdrawn	Treatment	Stage I Prostate Adenocarcinoma / Stage II Prostate Adenocarcinoma	1
2, 3	Completed	Not Available	Prostate Cancer	1
2, 3	Recruiting	Treatment	Stage I Prostate Adenocarcinoma / Stage II Prostate Adenocarcinoma / Stage III Prostate Adenocarcinoma	1
3	Active Not Recruiting	Treatment	Gastrointestinal Complications / Prostate Cancer / Sexual Dysfunctions / Urinary Complications	1
3	Active Not Recruiting	Treatment	Prostate Cancer	9
3	Active Not Recruiting	Treatment	Prostatic Neoplasms	1
3	Completed	Health Services Research	Prostate Cancer	1
3	Completed	Prevention	Prostate Cancer	1
3	Completed	Treatment	Non-Metastatic Prostate Cancer	3
3	Completed	Treatment	Prostate Cancer	14
3	Recruiting	Prevention	Metastatic Triple Negative Breast Cancer	1
3	Recruiting	Treatment	Castration Levels of Testosterone / Metastatic Prostatic Adenocarcinoma / Stage IV Prostate Cancer AJCC v8 / Stage IVA Prostate Cancer AJCC v8 / Stage IVB Prostate Cancer AJCC v8	1
3	Recruiting	Treatment	Hormone-dependent prostate cancer / Prostate Cancer	1
3	Recruiting	Treatment	Prostate Cancer	1
3	Terminated	Treatment	Prostate Cancer	5
3	Terminated	Treatment	Prostatic Neoplasms	1
3	Unknown Status	Treatment	Prostate Cancer	1
4	Completed	Treatment	Prostate Cancer	1
4	Completed	Treatment	Prostate Neoplasms	1
4	Not Yet Recruiting	Treatment	Advanced Prostate Cancer	1
4	Withdrawn	Treatment	Metastatic Hormone Refractory Prostate Cancer	1
Not Available	Active Not Recruiting	Not Available	Prostate Cancer	1
Not Available	Active Not Recruiting	Treatment	Prostate Cancer	1
Not Available	Active Not Recruiting	Treatment	Stage III Prostate Cancer	1
Not Available	Completed	Prevention	Osteoporosis	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	Adenocarcinoma, Prostate / Prostate Cancer	1
Not Available	Recruiting	Not Available	Prostate Cancer	1
Not Available	Recruiting	Not Available	Prostatic Neoplasms	1
Not Available	Recruiting	Treatment	Adenocarcinoma of the Prostate	1

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

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

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

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	>10000	N/A	N/A	18442912 / 22094279 / 22391033 / 23199477
EC 50 (nM)	157	N/A	N/A	10230628
IC 50 (nM)	>10	N/A	N/A	10230628
IC 50 (nM)	>100000	N/A	N/A	23301637
IC 50 (nM)	117	N/A	N/A	10230628
IC 50 (nM)	12000	7.2	23	19645433
IC 50 (nM)	128	7.4	37	17887661
IC 50 (nM)	140	N/A	N/A	17064916 / 17804229
IC 50 (nM)	157	N/A	N/A	9484511 / 9871534
IC 50 (nM)	162	N/A	N/A	18400499 / 18442912
IC 50 (nM)	162	7.4	37	17257838
IC 50 (nM)	170	N/A	N/A	15546739
IC 50 (nM)	173	N/A	N/A	15603938 / 15603960 / 18291644 / 20584610
IC 50 (nM)	200	N/A	N/A	17064916 / 17804229 / 20381361 / 21050768
IC 50 (nM)	232	N/A	N/A	18442912
IC 50 (nM)	300	N/A	N/A	20826091
IC 50 (nM)	330	N/A	N/A	22094279 / 22391033 / 23199477
IC 50 (nM)	338	N/A	N/A	10743937
IC 50 (nM)	400	N/A	N/A	15546739 / 15603938 / 15603960 / 20584610
IC 50 (nM)	54	N/A	N/A	22094279 / 22391033 / 23199477
IC 50 (nM)	550	N/A	N/A	20381361
IC 50 (nM)	600	N/A	N/A	21050768
IC 50 (nM)	725	N/A	N/A	15603938 / 15603960
IC 50 (nM)	890	7.8	N/A	16420057
Ki (nM)	117	N/A	N/A	9484511 / 10743937
Ki (nM)	151	N/A	N/A	18400499 / 18442912
Ki (nM)	151	7.4	37	17257838
Ki (nM)	35	N/A	N/A	15603938 / 15603960
Ki (nM)	64	N/A	N/A	15603938 / 15603960 / 18291644 / 20584610
Ki (nM)	65	N/A	N/A	15546739
Ki (nM)	70	7.4	37	17887661
Ki (nM)	82	N/A	N/A	9871534

Details1. 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

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

Details1. Cytochrome P450 3A4

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

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

Details2. Cytochrome P450 2C19

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

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

Details3. Cytochrome P450 2C9

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

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

Details4. Cytochrome P450 2D6

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

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 August 21, 2019 23:43

Bicalutamide

Identification

Structure for Bicalutamide (DB01128)

Pharmacology

Interactions

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

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Enzymes

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