Flutamide

Summary

Flutamide (CHEMBL806) is an approved small-molecule androgen antagonist (ATC L02BB01) targeting AR; indicated across 8 conditions including prostate carcinoma and neoplasm.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: L02BB01
• Targets: 1 (AR)
• Indications: 8 conditions
• Clinical trials: 56
• Chemistry: 276.21 Da · C11H11F3N2O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL806
Name	Flutamide
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	3397
ChEBI	CHEBI:5132
ATC	L02BB01
Molecular formula	C11H11F3N2O3
Molecular weight	276.21
InChIKey	MKXKFYHWDHIYRV-UHFFFAOYSA-N

SMILES: CC(C)C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F

IUPAC name: 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

Pharmacological roles (ChEBI): androgen antagonist, antineoplastic agent.

Also known as: Chimax, Drogenil, Eulexin, Flutamida, Flutamide, NSC-215876, SCH 13521, SCH-13521, flutamide, SID11111202, SID11111203, SID11532925

Patent coverage: 24,924 distinct patent families (99,079 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 98,682 (100%) 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	5.43		P10275

Broader ChEMBL bioactivity targets: 31 (assay-derived). Sample: Nuclear receptor ROR-gamma, Survival motor neuron protein, Prelamin-A/C, Ferritin light chain, Endonuclease 4, Peripheral myelin protein 22, Androgen receptor, Thyrotropin receptor, Beta-lactamase, Thromboxane A2 receptor.

Bioactivity

ChEMBL activities: 31 potent at pChembl ≥ 5 of 61 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
AR	7.26	Ki	55	nM	CHEMBL_ACT_25828637
LMNA	7.1	Potency	79.4	nM	CHEMBL_ACT_3645584
AR	6.81	IC50	154	nM	CHEMBL_ACT_1472580
AR	6.81	IC50	154	nM	CHEMBL_ACT_56112
CYP1A2	6.5	AC50	316.2	nM	CHEMBL_ACT_6034304
AR	6.24	IC50	580	nM	CHEMBL_ACT_2359328
AADAC	6.22	Ki	600	nM	CHEMBL_ACT_15454619
P00811	6.2	Potency	631	nM	CHEMBL_ACT_4718332
P0A6C1	6.05	Potency	891.3	nM	CHEMBL_ACT_4069511
AR	6	IC50	1000	nM	CHEMBL_ACT_3243510
AR	5.89	Ki	1300	nM	CHEMBL_ACT_588925
AR	5.8	AC50	1582	nM	CHEMBL_ACT_25203189
AR	5.7	IC50	2000	nM	CHEMBL_ACT_2603313
O70528	5.65	Ki	2258	nM	CHEMBL_ACT_7648785
CES2	5.64	Ki	2300	nM	CHEMBL_ACT_15461137
KCNH2	5.6	AC50	2528	nM	CHEMBL_ACT_25117327
AR	5.43	Ki	3700	nM	CHEMBL_ACT_2451959
AR	5.38	IC50	4200	nM	CHEMBL_ACT_2452715
CYP3A4	5.3	Potency	5012	nM	CHEMBL_ACT_4997799
CYP3A4	5.3	Potency	5012	nM	CHEMBL_ACT_5066508
CYP3A4	5.3	AC50	5012	nM	CHEMBL_ACT_6022973
CHRM1	5.24	AC50	5772	nM	CHEMBL_ACT_25210067
TBXA2R	5.22	AC50	6000	nM	CHEMBL_ACT_25197498
P08482	5.2	Potency	6310	nM	CHEMBL_ACT_4853850
P08482	5.15	Potency	7080	nM	CHEMBL_ACT_4803434
HTR6	5.08	Ki	8271	nM	CHEMBL_ACT_7648787
P15207	5.05	Ki	8927	nM	CHEMBL_ACT_7648801
ADRA1A	5.04	AC50	9045	nM	CHEMBL_ACT_25218708
SMN1	5	Potency	10000	nM	CHEMBL_ACT_3893479
CYP2C19	5	Potency	10000	nM	CHEMBL_ACT_4014324

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

8 indications (5 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
prostate carcinoma	4	MONDO:0005159	EFO:0001663
neoplasm	4	MONDO:0005070	EFO:0000616
prostate adenocarcinoma	4	MONDO:0005082	EFO:0000673
metastatic prostate carcinoma	4	MONDO:0004956	EFO:0000196
carcinoma	4	MONDO:0004993	EFO:0000313
polycystic ovary syndrome	2	MONDO:0008487	EFO:0000660
ovarian cancer	2	MONDO:0008170	MONDO:0008170

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

Clinical trials

Total trials: 56.

Phase distribution

Phase	Trials
PHASE3	24
PHASE2	17
PHASE1	4
Not specified	4
PHASE4	3
PHASE2/PHASE3	2
EARLY_PHASE1	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00611923	PHASE4	COMPLETED	Effectiveness of Flutamide in Treating Women With Premenstrual Dysphoric Disorder
NCT02918968	PHASE4	COMPLETED	Study on Enzalutamide and Flutamide in Patients With Castration Resistant Prostate Cancer
NCT04248621	PHASE4	UNKNOWN	Androgen Deprivation Therapy on Bone Mineral Density Change in Prostate Cancer Patients
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
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
NCT00001521	PHASE3	COMPLETED	Three Drug Combination Therapy Versus Conventional Treatment of Children With Congenital Adrenal Hyperplasia
NCT00002597	PHASE3	COMPLETED	Radiation Therapy With or Without Antiandrogen Therapy in Treating Patients With Stage I or Stage II Prostate Cancer
NCT00002633	PHASE3	COMPLETED	Hormone Therapy With or Without Surgery or Radiation Therapy in Treating Patients With Prostate Cancer
NCT00002855	PHASE3	COMPLETED	Chemotherapy Plus Hormone Therapy Versus Androgen Suppression in Treating Patients With Metastatic or Unresectable Prostate Cancer
NCT00002881	PHASE3	COMPLETED	Flutamide, Suramin, and Hydrocortisone in Treating Patients With Prostate Cancer
NCT00003026	PHASE3	COMPLETED	Hormone Therapy in Treating Patients With Advanced Prostate Cancer
NCT00003645	PHASE3	TERMINATED	Randomized Trial of Adjuvant Hormonal Therapy in Surgically Treated Prostate Cancer Patients at High Risk for Recurrence
NCT00003653	PHASE3	COMPLETED	Hormone Therapy in Treating Patients With Rising PSA Levels Following Radiation Therapy for Prostate Cancer
NCT00003734	PHASE3	UNKNOWN	Combination Hormone Therapy Followed by Radiation Therapy in Treating Patients With Prostate Cancer
NCT00004054	PHASE3	COMPLETED	Hormone Therapy Plus Radiation Therapy With or Without Combination Chemotherapy in Treating Patients With Prostate Cancer
NCT00005044	PHASE3	COMPLETED	Hormone Therapy and Radiation Therapy 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
NCT00104741	PHASE3	COMPLETED	Triptorelin, Flutamide, and External-Beam Radiation Therapy or External-Beam Radiation Therapy Alone in Treating Patients With Stage II or Stage III Prostate Cancer
NCT00388804	PHASE3	TERMINATED	External Beam Radiation Therapy (EBRT) With or Without Hormonal Therapy in Prostate Cancer
NCT00651326	PHASE3	TERMINATED	Androgen Suppression and Radiation With/Out Docetaxel in High-Risk Localized Prostate Cancer
NCT00767286	PHASE3	COMPLETED	Goserelin, Flutamine, and Radiation Therapy in Treating Patients With Locally Advanced Prostate Cancer
NCT00769548	PHASE3	COMPLETED	Radiation Therapy and Hormone Therapy in Treating Patients With Prostate Cancer
NCT00936390	PHASE3	COMPLETED	Radiation Therapy With or Without Androgen-Deprivation Therapy in Treating Patients With Prostate Cancer
NCT01011751	PHASE3	COMPLETED	Treatment of Hot Flushes Caused by Leuprorelin 11.25 mg in Prostate Adenocarcinoma
NCT01122121	PHASE3	COMPLETED	Leuprorelin Associated With Radiotherapy Versus Leuprorelin Alone in T3 - T4 or pT3 (on Biopsy) N0, M0 Prostate Cancer
NCT03070886	PHASE2/PHASE3	COMPLETED	Antiandrogen Therapy and Radiation Therapy With or Without Docetaxel in Treating Patients With Prostate Cancer That Has Been Removed by Surgery
NCT06601205	PHASE2/PHASE3	COMPLETED	Finasteride and Flutamide in Pre-surgical Trial in Prostate Cancer.
NCT01786265	PHASE2	ACTIVE_NOT_RECRUITING	Finite Androgen Ablation With or Without Abiraterone Acetate and Prednisone in Treating Patients With Recurrent Prostate Cancer
NCT06694350	PHASE2	NOT_YET_RECRUITING	Pembrolizumab in Combination with Flutamide Treatment for Recurrence / Metastasis HNSCC
NCT00002889	PHASE2	COMPLETED	Radiation Therapy With Androgen Suppression in Treating Patients With Prostate Cancer
NCT00003124	PHASE2	COMPLETED	Hormone Therapy Plus Radiation Therapy in Treating Patients With Prostate Cancer
NCT00003323	PHASE2	COMPLETED	Hormone Therapy in Treating Patients With Prostate Cancer
NCT00003517	PHASE2	WITHDRAWN	Antineoplaston Therapy in Treating Patients With Stage III or Stage IV Prostate Cancer
NCT00006214	PHASE2	COMPLETED	Flutamide In the Prevention of Prostate Cancer in Patients With Neoplasia of the Prostate
NCT00028769	PHASE2	COMPLETED	S0032, Combination Chemotherapy Plus Hormone Therapy in Treating Patients With Metastatic Prostate Cancer
NCT00170157	PHASE2	COMPLETED	Hormone Therapy and Ipilimumab in Treating Patients With Advanced Prostate Cancer
NCT00223665	PHASE2	COMPLETED	Effects of IAS in Men With Localized Biochemical Relapsed Prostate Cancer
NCT00450463	PHASE2	COMPLETED	Vaccine Therapy With PROSTVAC/TRICOM and Flutamide Versus Flutamide Alone to Treat Prostate Cancer

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

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
BICALUTAMIDE	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
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