Bicalutamide

Summary

Bicalutamide (CHEMBL409) is an approved small molecule (ATC L02BB03) targeting AR; indicated across 19 conditions including neoplasm and carcinoma.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: L02BB03
• Targets: 1 (AR)
• Indications: 19 conditions
• Clinical trials: 163
• Chemistry: 430.4 Da · C18H14F4N2O4S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL409
Name	Bicalutamide
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	2375
ChEBI	CHEBI:144093
ATC	L02BB03
Molecular formula	C18H14F4N2O4S
Molecular weight	430.4
InChIKey	LKJPYSCBVHEWIU-UHFFFAOYSA-N

SMILES: CC(CS(=O)(=O)C1=CC=C(C=C1)F)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O

IUPAC name: N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfonyl-2-hydroxy-2-methylpropanamide

ChEBI definition: A member of the class of (trifluoromethyl)benzenes that is 4-amino-2-(trifluoromethyl)benzonitrile in which one of the amino hydrogens is substituted by a 3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanoyl group.

Also known as: Bicalutamida, Bicalutamide, Casodex, Calutide, Cosudex, ICI 176,334, ICI-176334, Kalumid, NSC-759816, bicalutamide, SID26719836, SID50112740

Patent coverage: 20,621 distinct patent families (86,587 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 86,149 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
AR	Androgen receptor	Antagonist	6		P10275

Broader ChEMBL bioactivity targets: 12 (assay-derived). Sample: Nuclear receptor ROR-gamma, Androgen receptor, Alpha-2C adrenergic receptor, Beta-lactamase, Progesterone receptor, Progesterone receptor, Androgen receptor, Androgen receptor, Albumin, Progesterone receptor.

Bioactivity

ChEMBL activities: 98 potent at pChembl ≥ 5 of 106 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
AR	7.96	Ki	11	nM	CHEMBL_ACT_24775601
P15207	7.85	Ki	14	nM	CHEMBL_ACT_1673720
AR	7.72	Ki	19	nM	CHEMBL_ACT_1673719
P15207	7.6	IC50	25	nM	CHEMBL_ACT_7846345
AR	7.51	EC50	31	nM	CHEMBL_ACT_13344973
AR	7.46	Ki	35	nM	CHEMBL_ACT_1422157
AR	7.46	Ki	35	nM	CHEMBL_ACT_1436714
AR	7.4	Ki	40	nM	CHEMBL_ACT_28423493
AR	7.27	IC50	54	nM	CHEMBL_ACT_12691774
P15207	7.27	IC50	54	nM	CHEMBL_ACT_5246402
AR	7.27	IC50	54	nM	CHEMBL_ACT_7993820
AR	7.27	IC50	54	nM	CHEMBL_ACT_8045689
AR	7.19	Ki	64	nM	CHEMBL_ACT_1422155
AR	7.19	Ki	64	nM	CHEMBL_ACT_1436712
AR	7.19	Ki	65	nM	CHEMBL_ACT_1462706
AR	7.19	Ki	64	nM	CHEMBL_ACT_15727983
AR	7.19	Ki	64	nM	CHEMBL_ACT_2114772
AR	7.19	Ki	64	nM	CHEMBL_ACT_3378633
AR	7.09	Ki	82	nM	CHEMBL_ACT_276505
AR	7.06	IC50	86.9	nM	CHEMBL_ACT_15198856
AR	7.06	IC50	86.9	nM	CHEMBL_ACT_15198866
AR	6.93	IC50	117	nM	CHEMBL_ACT_525160
AR	6.93	Ki	117	nM	CHEMBL_ACT_528695
AR	6.93	Ki	117	nM	CHEMBL_ACT_928197
AR	6.92	IC50	120	nM	CHEMBL_ACT_12691759
AR	6.92	IC50	120.2	nM	CHEMBL_ACT_24824257
AR	6.92	IC50	120	nM	CHEMBL_ACT_7993845
AR	6.92	IC50	120	nM	CHEMBL_ACT_8045712
AR	6.85	IC50	140	nM	CHEMBL_ACT_1852555
AR	6.85	IC50	140	nM	CHEMBL_ACT_1985110

Target pathways

Aggregated over 1 target gene(s): AR.

Top Reactome pathways

23 total, by targets touching each:

Pathway	Targets	Genes
Signal Transduction	1	AR
Signaling by Rho GTPases	1	AR
RHO GTPase Effectors	1	AR
Generic Transcription Pathway	1	AR
Cellular responses to stress	1	AR
SUMOylation	1	AR
SUMO E3 ligases SUMOylate target proteins	1	AR
HSP90 chaperone cycle for steroid hormone receptors (SHR) in the presence of ligand	1	AR
Nuclear Receptor transcription pathway	1	AR
Metabolism of proteins	1	AR
SUMOylation of intracellular receptors	1	AR
RHO GTPases activate PKNs	1	AR
Activated PKN1 stimulates transcription of AR (androgen receptor) regulated genes KLK2 and KLK3	1	AR
Deubiquitination	1	AR
Ub-specific processing proteases	1	AR
Post-translational protein modification	1	AR
RNA Polymerase II Transcription	1	AR
Gene expression (Transcription)	1	AR
Transcriptional regulation by RUNX2	1	AR
RUNX2 regulates osteoblast differentiation	1	AR
RUNX2 regulates bone development	1	AR
Cellular responses to stimuli	1	AR
Signaling by Rho GTPases, Miro GTPases and RHOBTB3	1	AR

Dominant GO biological processes

GO term	Targets
negative regulation of transcription by RNA polymerase II	1
MAPK cascade	1
in utero embryonic development	1
regulation of systemic arterial blood pressure	1
epithelial cell morphogenesis	1
transcription by RNA polymerase II	1
signal transduction	1
cell-cell signaling	1
spermatogenesis	1
single fertilization	1
positive regulation of cell population proliferation	1
negative regulation of cell population proliferation	1
male gonad development	1
positive regulation of gene expression	1
male somatic sex determination	1

Indications & clinical

Indications

19 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
neoplasm	4	MONDO:0005070	EFO:0000616
carcinoma	4	MONDO:0004993	EFO:0000313
prostate adenocarcinoma	3	MONDO:0005082	EFO:0000673
metastatic prostate carcinoma	3	MONDO:0004956	EFO:0000196
prostate carcinoma	3	MONDO:0005159	EFO:0001663
breast carcinoma	3	MONDO:0004989	EFO:0000305
breast neoplasm	3	MONDO:0021100	EFO:0003869
severe acute respiratory syndrome	3	MONDO:0005091	EFO:0000694
gynecomastia disorder	2	MONDO:0001571	HP:0000771
precocious puberty	2	MONDO:0000088	MONDO:0000088
peritoneal neoplasm	2	MONDO:0006901	MONDO:0002087
fallopian tube neoplasm	2	MONDO:0021092	MONDO:0002158
salivary gland cancer	2	MONDO:0004669	MONDO:0004669
ovarian cancer	2	MONDO:0008170	MONDO:0008170
urothelial carcinoma	2	MONDO:0040679	EFO:0008528

4 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 163.

Phase distribution

Phase	Trials
PHASE2	70
PHASE3	40
PHASE1	23
Not specified	11
PHASE1/PHASE2	8
PHASE4	6
PHASE2/PHASE3	3
EARLY_PHASE1	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00255268	PHASE4	WITHDRAWN	CMAB vs IMAB in Metastatic Prostate Cancer
NCT00293696	PHASE4	COMPLETED	Casodex/Zoladex Biomarkers in Localised Prostate Cancer
NCT00470834	PHASE4	COMPLETED	Prostate Cancer Study In Men Who Have Failed First-Line Androgen Deprivation Therapy
NCT00590213	PHASE4	COMPLETED	Compare the Value of Prophylactic Versus Therapeutic Breast Radiotherapy in CASODEX
NCT03971110	PHASE4	TERMINATED	A Study of Neoadjuvant Hormone Therapy in Patient With Advanced Prostate Cancer Undergoing Radical Prostatectomy.
NCT04248621	PHASE4	UNKNOWN	Androgen Deprivation Therapy on Bone Mineral Density Change in Prostate Cancer Patients
NCT02531516	PHASE3	ACTIVE_NOT_RECRUITING	An Efficacy and Safety Study of JNJ-56021927 (Apalutamide) in High-risk Prostate Cancer Subjects Receiving Primary Radiation Therapy: ATLAS
NCT03458221	PHASE2/PHASE3	RECRUITING	Signal TrAnsduction Pathway Activity Analysis in OVarian cancER
NCT03678025	PHASE3	RECRUITING	Standard Systemic Therapy With or Without Definitive Treatment in Treating Participants With Metastatic Prostate Cancer
NCT04513717	PHASE3	ACTIVE_NOT_RECRUITING	Two Studies for Patients With High Risk Prostate Cancer Testing Less Intense Treatment for Patients With a Low Gene Risk Score and Testing a More Intense Treatment for Patients With a High Gene Risk Score, The PREDICT-RT Trial
NCT05019846	PHASE3	RECRUITING	SRT Versus SRT+ADT in Prostate Cancer
NCT05050084	PHASE3	ACTIVE_NOT_RECRUITING	Two Studies for Patients With Unfavorable Intermediate Risk Prostate Cancer Testing Less Intense Treatment for Patients With a Low Gene Risk Score and Testing a More Intense Treatment for Patients With a Higher Gene Risk Score, The Guidance Trial
NCT06650579	PHASE3	RECRUITING	REVELUTION-2: Relugolix+Abiraterone Acetate (AA) Versus Leuprolide+AA Cardiac Trial
NCT00002633	PHASE3	COMPLETED	Hormone Therapy With or Without Surgery or Radiation Therapy in Treating Patients With Prostate Cancer
NCT00002651	PHASE3	COMPLETED	SWOG-9346, Hormone Therapy in Treating Men With Stage IV Prostate Cancer
NCT00002855	PHASE3	COMPLETED	Chemotherapy Plus Hormone Therapy Versus Androgen Suppression in Treating Patients With Metastatic or Unresectable Prostate Cancer
NCT00002874	PHASE3	COMPLETED	Radiation Therapy With or Without Bicalutamide for Recurrent pT3N0 Prostate Cancer After Radical Prostatectomy
NCT00003026	PHASE3	COMPLETED	Hormone Therapy in Treating Patients With Advanced Prostate Cancer
NCT00003653	PHASE3	COMPLETED	Hormone Therapy in Treating Patients With Rising PSA Levels Following Radiation Therapy for Prostate Cancer
NCT00004054	PHASE3	COMPLETED	Hormone Therapy Plus Radiation Therapy With or Without Combination Chemotherapy in Treating Patients With Prostate Cancer
NCT00004124	PHASE3	COMPLETED	S9921, Hormone Therapy With or Without Mitoxantrone and Prednisone in Patients Who Have Undergone Radical Prostatectomy for Prostate Cancer
NCT00005044	PHASE3	COMPLETED	Hormone Therapy and Radiation Therapy in Treating Patients With Prostate Cancer
NCT00014586	PHASE3	TERMINATED	Bicalutamide Compared With Observation Followed by Bicalutamide Plus Either Goserelin or Orchiectomy in Treating Patients With Prostate Cancer
NCT00021450	PHASE3	COMPLETED	Radiation Therapy With or Without Bicalutamide and Goserelin in Treating Patients With Prostate Cancer
NCT00023829	PHASE3	COMPLETED	Adjuvant Radiation Therapy Plus Hormone Therapy Compared With Radiation Therapy Alone in Treating Patients With Stage II or Stage III Prostate Cancer
NCT00030654	PHASE3	COMPLETED	Hormone Therapy Plus Chemotherapy in Treating Patients With Prostate Cancer
NCT00055731	PHASE3	COMPLETED	Hormone Therapy With or Without Docetaxel And Estramustine in Treating Patients With Prostate Cancer That is Locally Advanced or At High Risk of Relapse
NCT00067015	PHASE3	COMPLETED	Radiation Therapy With or Without Bicalutamide and Goserelin in Treating Patients With Prostate Cancer
NCT00233610	PHASE3	COMPLETED	Two Different Regimens of Nolvadex in Preventing Gynecomastia Induced by Casodex 150 mg in Patients With Prostate Cancer
NCT00243646	PHASE3	TERMINATED	Implant and External Radiation for Prostate Cancer With or Without Hormonal Therapy: A Prospective Randomized Trial
NCT00388804	PHASE3	TERMINATED	External Beam Radiation Therapy (EBRT) With or Without Hormonal Therapy in Prostate Cancer
NCT00421694	PHASE2/PHASE3	COMPLETED	Positive Surgical Margins Rate and EGFR Family Members Expression in Prostate Cancer Treated With Bicalutamide
NCT00514917	PHASE3	TERMINATED	A Study of Androgen Deprivation With Leuprolide, +/- Docetaxel for Clinically Asymptomatic Prostate Cancer Participants With a Rising Prostate Specific Antigen (PSA)
NCT00541047	PHASE3	COMPLETED	RADICALS - Radiotherapy and Androgen Deprivation In Combination After Local Surgery
NCT00651326	PHASE3	TERMINATED	Androgen Suppression and Radiation With/Out Docetaxel in High-Risk Localized Prostate Cancer
NCT00657904	PHASE3	COMPLETED	Bicalutamide (Casodex™) Versus Placebo in Patients With Early Prostate Cancer
NCT00672282	PHASE3	COMPLETED	Casodex vs Placebo in Non-Metastatic Early Prostate Cancer
NCT00673205	PHASE3	COMPLETED	(Bicalutamide) Casodex vs Placebo in Non-metastatic Early Prostate Cancer
NCT00831233	PHASE3	TERMINATED	Symptomatic Study Investigating Degarelix in Patients Suffering From Prostate Cancer
NCT00833248	PHASE3	COMPLETED	Neoadjuvant Study Investigating Degarelix in Patients Suffering From Prostate Cancer

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 1 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

129 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
MEGESTROL	ChEMBL + PubChem	Phase 4 (approved)	AR
ABIRATERONE	ChEMBL	Phase 4 (approved)	AR
APALUTAMIDE	ChEMBL	Phase 4 (approved)	AR
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	AR
BECLOMETHASONE DIPROPIONATE	ChEMBL	Phase 4 (approved)	AR
BETAMETHASONE	ChEMBL	Phase 4 (approved)	AR
BITHIONOL	ChEMBL	Phase 4 (approved)	AR
BROMHEXINE	ChEMBL	Phase 4 (approved)	AR
BUDESONIDE	ChEMBL	Phase 4 (approved)	AR
CHLORMADINONE	ChEMBL	Phase 4 (approved)	AR
CLARITHROMYCIN	ChEMBL	Phase 4 (approved)	AR
CLASCOTERONE	ChEMBL	Phase 4 (approved)	AR
CLOCORTOLONE PIVALATE	ChEMBL	Phase 4 (approved)	AR
CLOMIPHENE	ChEMBL	Phase 4 (approved)	AR
CORTISONE	ChEMBL	Phase 4 (approved)	AR
CYCLOFENIL	ChEMBL	Phase 4 (approved)	AR
DAROLUTAMIDE	ChEMBL	Phase 4 (approved)	AR
DESOGESTREL	ChEMBL	Phase 4 (approved)	AR
DESOXIMETASONE	ChEMBL	Phase 4 (approved)	AR
DEXAMETHASONE	ChEMBL	Phase 4 (approved)	AR
DIETHYLSTILBESTROL	ChEMBL	Phase 4 (approved)	AR
DIFLORASONE DIACETATE	ChEMBL	Phase 4 (approved)	AR
DORZOLAMIDE	ChEMBL	Phase 4 (approved)	AR
DROSPIRENONE	ChEMBL	Phase 4 (approved)	AR
DYDROGESTERONE	ChEMBL	Phase 4 (approved)	AR
ENZALUTAMIDE	ChEMBL	Phase 4 (approved)	AR
EPLERENONE	ChEMBL	Phase 4 (approved)	AR
ESTRADIOL	ChEMBL	Phase 4 (approved)	AR
ESTRADIOL CYPIONATE	ChEMBL	Phase 4 (approved)	AR
ESTRADIOL VALERATE	ChEMBL	Phase 4 (approved)	AR
ESTRIOL	ChEMBL	Phase 4 (approved)	AR
ESTRONE	ChEMBL	Phase 4 (approved)	AR
ETHINYL ESTRADIOL	ChEMBL	Phase 4 (approved)	AR
ETHYNODIOL DIACETATE	ChEMBL	Phase 4 (approved)	AR
ETONOGESTREL	ChEMBL	Phase 4 (approved)	AR
FLUMETHASONE PIVALATE	ChEMBL	Phase 4 (approved)	AR
FLUOCINOLONE ACETONIDE	ChEMBL	Phase 4 (approved)	AR
FLUOCINONIDE	ChEMBL	Phase 4 (approved)	AR
FLUOXYMESTERONE	ChEMBL	Phase 4 (approved)	AR
FLURANDRENOLIDE	ChEMBL	Phase 4 (approved)	AR
FLUTAMIDE	ChEMBL	Phase 4 (approved)	AR
FLUTICASONE FUROATE	ChEMBL	Phase 4 (approved)	AR
FLUTICASONE PROPIONATE	ChEMBL	Phase 4 (approved)	AR
HALCINONIDE	ChEMBL	Phase 4 (approved)	AR
HALOBETASOL PROPIONATE	ChEMBL	Phase 4 (approved)	AR
HEXACHLOROPHENE	ChEMBL	Phase 4 (approved)	AR
HEXESTROL	ChEMBL	Phase 4 (approved)	AR
HYDROCORTISONE	ChEMBL	Phase 4 (approved)	AR
INDOMETHACIN	ChEMBL	Phase 4 (approved)	AR
LEVONORGESTREL	ChEMBL	Phase 4 (approved)	AR
MEDROXYPROGESTERONE	ChEMBL	Phase 4 (approved)	AR
METHYLPREDNISOLONE	ChEMBL	Phase 4 (approved)	AR
MIFEPRISTONE	ChEMBL	Phase 4 (approved)	AR
MOMETASONE FUROATE	ChEMBL	Phase 4 (approved)	AR
NILUTAMIDE	ChEMBL	Phase 4 (approved)	AR
NOMEGESTROL	ChEMBL	Phase 4 (approved)	AR
NORETHINDRONE	ChEMBL	Phase 4 (approved)	AR
NORETHYNODREL	ChEMBL	Phase 4 (approved)	AR
OXANDROLONE	ChEMBL	Phase 4 (approved)	AR
OXICONAZOLE	ChEMBL	Phase 4 (approved)	AR