Nilutamide
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Also known as AnadronNilandronNilutamidaNSC-758683RU 23908RU-23908SID11111555SID11111556SID11114201SID26747174SID26752242SID50104947SID56463082SID90341288SID85231160SID104171203SID26747175SID50104948SID50104949
Summary
Nilutamide (CHEMBL1274) is an approved small-molecule antineoplastic agent (ATC L02BB02) targeting AR; indicated across 4 conditions including neoplasm and prostate adenocarcinoma; with CIViC clinical evidence for 1 variant-indication association (e.g. AR Mutation in prostate cancer).
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: L02BB02
- Targets: 1 (AR)
- Indications: 4 conditions
- Clinical trials: 10
- Precision-oncology evidence (CIViC): 1 variant–indication association
- Chemistry: 317.22 Da · C12H10F3N3O4
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1274 |
| Name | Nilutamide |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 4493 |
| ChEBI | CHEBI:7573 |
| ATC | L02BB02 |
| Molecular formula | C12H10F3N3O4 |
| Molecular weight | 317.22 |
| InChIKey | XWXYUMMDTVBTOU-UHFFFAOYSA-N |
SMILES: CC1(C(=O)N(C(=O)N1)C2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)C
IUPAC name: 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
Pharmacological roles (ChEBI): antineoplastic agent, androgen antagonist.
Also known as: Anadron, Nilandron, Nilutamida, Nilutamide, NSC-758683, RU 23908, RU-23908, SID11111555, SID11111556, SID11114201, SID26747174, SID26752242
Patent coverage: 14,707 distinct patent families (64,154 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 64,013 (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 | 7.12 | P10275 |
Broader ChEMBL bioactivity targets: 20 (assay-derived). Sample: Nuclear receptor ROR-gamma, Survival motor neuron protein, Prelamin-A/C, Ras-related protein Rab-9A, Androgen receptor, Thyrotropin receptor, Progesterone receptor, Menin/Histone-lysine N-methyltransferase MLL, Muscarinic acetylcholine receptor M1, 3’,5’-cyclic-AMP phosphodiesterase 4D.
Bioactivity
ChEMBL activities: 26 potent at pChembl ≥ 5 of 46 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| P08482 | 8.8 | Potency | 1.6 | nM | CHEMBL_ACT_4803511 |
| AR | 8.05 | IC50 | 9 | nM | CHEMBL_ACT_1472449 |
| AR | 8.05 | IC50 | 9 | nM | CHEMBL_ACT_57340 |
| AR | 7.1 | AC50 | 80 | nM | CHEMBL_ACT_25203542 |
| TSHR | 6.9 | Potency | 125.9 | nM | CHEMBL_ACT_3912221 |
| CYP2C19 | 6.9 | Potency | 125.9 | nM | CHEMBL_ACT_4018433 |
| CYP2C19 | 6.9 | AC50 | 125.9 | nM | CHEMBL_ACT_6056394 |
| CYP2C19 | 6.6 | Potency | 251.2 | nM | CHEMBL_ACT_4016258 |
| CYP2C19 | 6.6 | AC50 | 251.2 | nM | CHEMBL_ACT_6004302 |
| AR | 6.22 | IC50 | 600 | nM | CHEMBL_ACT_22453857 |
| P15207 | 6.05 | AC50 | 883 | nM | CHEMBL_ACT_25232901 |
| LMNA | 5.75 | Potency | 1778 | nM | CHEMBL_ACT_3639870 |
| P15207 | 5.68 | AC50 | 2100 | nM | CHEMBL_ACT_25232359 |
| CYP1A2 | 5.6 | AC50 | 2512 | nM | CHEMBL_ACT_6012065 |
| CYP1A2 | 5.5 | AC50 | 3162 | nM | CHEMBL_ACT_6055369 |
| CYP3A4 | 5.4 | Potency | 3981 | nM | CHEMBL_ACT_4969553 |
| CYP3A4 | 5.4 | Potency | 3981 | nM | CHEMBL_ACT_5034853 |
| CYP3A4 | 5.4 | AC50 | 3981 | nM | CHEMBL_ACT_6057277 |
| AR | 5.3 | IC50 | 5000 | nM | CHEMBL_ACT_24775612 |
| ALOX12 | 5.2 | Potency | 6310 | nM | CHEMBL_ACT_4527154 |
| P15207 | 5.16 | AC50 | 6933 | nM | CHEMBL_ACT_25187495 |
| NFKB1 | 5.15 | Potency | 7080 | nM | CHEMBL_ACT_3671909 |
| NFKB1 | 5.15 | Potency | 7080 | nM | CHEMBL_ACT_4585191 |
| SMN1 | 5.1 | Potency | 7943 | nM | CHEMBL_ACT_3874023 |
| CYP2C19 | 5.1 | Potency | 7943 | nM | CHEMBL_ACT_4016391 |
| P51450 | 5.05 | Potency | 8912 | nM | CHEMBL_ACT_4818790 |
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
4 indications (4 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 |
| prostate adenocarcinoma | 4 | MONDO:0005082 | EFO:0000673 |
| prostate cancer | 4 | MONDO:0008315 | MONDO:0008315 |
| metastatic prostate carcinoma | 4 | MONDO:0004956 | EFO:0000196 |
Clinical trials
Total trials: 10.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 4 |
| PHASE2 | 4 |
| PHASE2/PHASE3 | 1 |
| PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT03678025 | PHASE3 | RECRUITING | Standard Systemic Therapy With or Without Definitive Treatment in Treating Participants With Metastatic 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 |
| NCT00003653 | PHASE3 | COMPLETED | Hormone Therapy in Treating Patients With Rising PSA Levels Following Radiation Therapy for 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 |
| NCT01786265 | PHASE2 | ACTIVE_NOT_RECRUITING | Finite Androgen Ablation With or Without Abiraterone Acetate and Prednisone in Treating Patients With Recurrent Prostate Cancer |
| NCT00020254 | PHASE2 | COMPLETED | Vaccine Therapy Plus Sargramostim and Interleukin-2 Compared With Nilutamide Alone in Treating Patients With Prostate Cancer |
| NCT00028769 | PHASE2 | COMPLETED | S0032, Combination Chemotherapy Plus Hormone Therapy in Treating Patients With Metastatic Prostate Cancer |
| NCT00918385 | PHASE2 | TERMINATED | Genomic Guided Therapy With Dasatinib or Nilutamide in Metastatic Castration-Resistant Prostate Cancer |
| NCT00512668 | PHASE1 | TERMINATED | Hormone Therapy and Temsirolimus in Treating Patients With Relapsed Prostate Cancer |
Clinical evidence (CIViC)
Variant × indication × effect (1 predictive associations from 1 curated evidence items):
| Variant | Indication | Effect | Therapy | Level | CIViC |
|---|---|---|---|---|---|
| AR Mutation | Prostate Cancer | Resistance | Flutamide + Cyproterone Acetate + Nilutamide + Bicalutamide | CIViC B | EID1521 |
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 |
| 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 |
| 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 |
Related Atlas pages
- Genes: AR
- Diseases: neoplasm, prostate adenocarcinoma, prostate cancer, metastatic prostate carcinoma, prostate carcinoma
- Drugs: Megestrol, Abiraterone, Apalutamide, Aripiprazole, Beclomethasone Dipropionate, Betamethasone, Bicalutamide, Bithionol, Bromhexine, Budesonide, Chlormadinone, Clarithromycin, Clascoterone, Clocortolone Pivalate, Clomiphene, Cortisone, Cyclofenil, Darolutamide, Desogestrel, Desoximetasone, Dexamethasone, Diethylstilbestrol, Diflorasone Diacetate, Dorzolamide, Drospirenone, Dydrogesterone, Enzalutamide, Eplerenone, Estradiol, Estradiol Cypionate, Estradiol Valerate, Estriol, Estrone, Ethinyl Estradiol, Ethynodiol Diacetate, Etonogestrel, Flumethasone Pivalate, Fluocinolone Acetonide, Fluocinonide, Fluoxymesterone, Flurandrenolide, Flutamide, Fluticasone Furoate, Fluticasone Propionate, Halcinonide, Halobetasol Propionate, Hexachlorophene, Hexestrol, Hydrocortisone, Indomethacin, Levonorgestrel, Medroxyprogesterone, Methylprednisolone, Mifepristone, Mometasone Furoate, Norethindrone, Norethynodrel, Oxandrolone, Oxiconazole