U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H10F3N3O4
Molecular Weight 317.2207
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NILUTAMIDE

SMILES

CC1(C)NC(=O)N(C1=O)C2=CC(=C(C=C2)[N+]([O-])=O)C(F)(F)F

InChI

InChIKey=XWXYUMMDTVBTOU-UHFFFAOYSA-N
InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20)

HIDE SMILES / InChI
Molecular Formula C12H10F3N3O4
Molecular Weight 317.2207
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf

Nilutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Nilutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Nilutamide blocks the action of androgens of adrenal and testicular origin that 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. The relative binding affinity of nilutamide at the androgen receptor is less than that of bicalutamide, but similar to that of hydroxuflutamide. Nilutamide competes with androgen for the binding of androgen receptors, consequently blocking the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. This blockade of androgen receptors may result in growth arrest or transient tumor regression through inhibition of androgen-dependent DNA and protein synthesis. Nilutamide is used in combination with surgical castration for the treatment of metastatic prostate cancer involving distant lymph nodes, bone, or visceral organs (Stage D2). Nilutamide is sold under the brand names Nilandron (US), Anandron (CA)).

CNS Activity

CNS Penetrant
2588
Curator's Comment: Like flutamide and bicalutamide, nilutamide is able to cross the blood-brain-barrier and has central antiandrogen actions.

Originator

Approval Year

1996
224
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 9.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
NILANDRON

Approved Use

Metastatic Prostate Cancer Nilutamide Tablets are indicated for use in combination with surgical castration for the treatment of metastatic prostate cancer (Stage D2).

Launch Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.3 mg/L
DRUG LABEL
https://gp2u.com.au/static/pdf/A/ANANDRON-PI.pdf
0.3 g single, oral
dose: 0.3 g
route of administration: Oral
experiment type: SINGLE
co-administered:
NILUTAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2.3 mg/L
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/8453188
0.3 g single, oral
dose: 0.3 g
route of administration: Oral
experiment type: SINGLE
co-administered:
NILUTAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
84 mg × h/L
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/8453188
0.3 g single, oral
dose: 0.3 g
route of administration: Oral
experiment type: SINGLE
co-administered:
NILUTAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
56 h
DRUG LABEL
https://gp2u.com.au/static/pdf/A/ANANDRON-PI.pdf
0.3 g single, oral
dose: 0.3 g
route of administration: Oral
experiment type: SINGLE
co-administered:
NILUTAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
49 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/8453188
0.3 g single, oral
dose: 0.3 g
route of administration: Oral
experiment type: SINGLE
co-administered:
NILUTAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
unhealthy, 47-93
Health Status: unhealthy
Age Group: 47-93
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
DLT: Nausea, Vomiting...
Disc. AE: Hot flashes, Interstitial lung disease...
Dose limiting toxicities:
Nausea (7.5%)
Vomiting (7.5%)
AEs leading to
discontinuation/dose reduction:
Hot flashes (5.7%)
Interstitial lung disease (3.8%)
Visual disturbance NOS (1.9%)
Pruritus (1.9%)
Dizziness (1.9%)
Headache (1.9%)
Hepatic enzyme increased (1.9%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
13 g single, oral
Overdose
Dose: 13 g
Route: oral
Route: single
Dose: 13 g
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
unhealthy, 79
Health Status: unhealthy
Age Group: 79
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
Disc. AE: Vomiting, Diarrhoea...
AEs leading to
discontinuation/dose reduction:
Vomiting (moderate)
Diarrhoea (moderate)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
900 mg 1 times / day multiple, oral
Highest studied dose
Dose: 900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 900 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
Disc. AE: Gastrointestinal disorders, Nausea...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal disorders
Nausea
Vomiting
Malaise
Headache
Dizziness
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
Disc. AE: Interstitial pneumonitis, Pulmonary fibrosis...
AEs leading to
discontinuation/dose reduction:
Interstitial pneumonitis (2%)
Pulmonary fibrosis (grade 5, rare)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
Disc. AE: Liver injury...
AEs leading to
discontinuation/dose reduction:
Liver injury (severe, rare)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
Disc. AE: Visual disturbances...
AEs leading to
discontinuation/dose reduction:
Visual disturbances (1 - 2)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Dizziness 1.9%
Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
unhealthy, 47-93
Health Status: unhealthy
Age Group: 47-93
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
Headache 1.9%
Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
unhealthy, 47-93
Health Status: unhealthy
Age Group: 47-93
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
Hepatic enzyme increased 1.9%
Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
unhealthy, 47-93
Health Status: unhealthy
Age Group: 47-93
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
Pruritus 1.9%
Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
unhealthy, 47-93
Health Status: unhealthy
Age Group: 47-93
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
Visual disturbance NOS 1.9%
Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
unhealthy, 47-93
Health Status: unhealthy
Age Group: 47-93
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
Interstitial lung disease 3.8%
Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
unhealthy, 47-93
Health Status: unhealthy
Age Group: 47-93
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
Hot flashes 5.7%
Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
unhealthy, 47-93
Health Status: unhealthy
Age Group: 47-93
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
Nausea 7.5%
DLT
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
unhealthy, 47-93
Health Status: unhealthy
Age Group: 47-93
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
Vomiting 7.5%
DLT
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
unhealthy, 47-93
Health Status: unhealthy
Age Group: 47-93
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/2203517
Diarrhoea moderate
Disc. AE
13 g single, oral
Overdose
Dose: 13 g
Route: oral
Route: single
Dose: 13 g
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
unhealthy, 79
Health Status: unhealthy
Age Group: 79
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
Vomiting moderate
Disc. AE
13 g single, oral
Overdose
Dose: 13 g
Route: oral
Route: single
Dose: 13 g
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
unhealthy, 79
Health Status: unhealthy
Age Group: 79
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
Dizziness Disc. AE
900 mg 1 times / day multiple, oral
Highest studied dose
Dose: 900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 900 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
Gastrointestinal disorders Disc. AE
900 mg 1 times / day multiple, oral
Highest studied dose
Dose: 900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 900 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
Headache Disc. AE
900 mg 1 times / day multiple, oral
Highest studied dose
Dose: 900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 900 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
Malaise Disc. AE
900 mg 1 times / day multiple, oral
Highest studied dose
Dose: 900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 900 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
Nausea Disc. AE
900 mg 1 times / day multiple, oral
Highest studied dose
Dose: 900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 900 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
Vomiting Disc. AE
900 mg 1 times / day multiple, oral
Highest studied dose
Dose: 900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 900 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/2810141
Interstitial pneumonitis 2%
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
Pulmonary fibrosis grade 5, rare
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
Liver injury severe, rare
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
Visual disturbances 1 - 2
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
unhealthy
Health Status: unhealthy
Sex: M
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:7573
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7573
ChemicalBook
CB3278091
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3278091
eMolecules
592881
https://www.emolecules.com/cgi-bin/more?vid=592881
MolPort
MolPort-003-666-533
https://www.molport.com/shop/molecule-link/MolPort-003-666-533
MolPort
MolPort-005-975-300
https://www.molport.com/shop/molecule-link/MolPort-005-975-300
ZINC
ZINC000003874498
http://zinc15.docking.org/substances/ZINC000003874498
PubMed

PubMed

TitleDatePubMed
Activity of antiandrogens against juvenile and adult Schistosoma mansoni in mice.
2010-09
Maximal androgen blockade for advanced prostate cancer.
2010-06-11
Involvement of androgen receptor in nitric oxide production induced by icariin in human umbilical vein endothelial cells.
2010-06-03
The evolutionary impact of androgen levels on prostate cancer in a multi-scale mathematical model.
2010-04-20
Androgen receptor-dependent activation of endothelial nitric oxide synthase in vascular endothelial cells: role of phosphatidylinositol 3-kinase/akt pathway.
2010-04
A randomized phase II trial of mitoxantrone, estramustine and vinorelbine or bcl-2 modulation with 13-cis retinoic acid, interferon and paclitaxel in patients with metastatic castrate-resistant prostate cancer: ECOG 3899.
2010-02-24
Growth inhibition of androgen-responsive prostate cancer cells with brefeldin A targeting cell cycle and androgen receptor.
2010-01-26
Hormonal therapy of prostate cancer.
2010
Fasting and cancer treatment in humans: A case series report.
2009-12-31
Efficacy of salvage radiotherapy plus 2-year androgen suppression for postradical prostatectomy patients with PSA relapse.
2009-11-15
Prospective study evaluating postoperative radiotherapy plus 2-year androgen suppression for post-radical prostatectomy patients with pathologic T3 disease and/or positive surgical margins.
2009-10-01
Integrating statistical predictions and experimental verifications for enhancing protein-chemical interaction predictions in virtual screening.
2009-06
Fulminant hepatic failure due to nilutamide hepatotoxicity.
2009-04
CYP17 blockade by abiraterone: further evidence for frequent continued hormone-dependence in castration-resistant prostate cancer.
2009-03-10
Impact level of dihydrotestosterone on the hypothalamic-pituitary-leydig cell axis in men.
2009-02
Genotoxic and endocrine activities of bis(hydroxyphenyl)methane (bisphenol F) and its derivatives in the HepG2 cell line.
2009-01-08
Role of maximum androgen blockade in advanced prostate cancer.
2009-01
A dramatic, objective antiandrogen withdrawal response: case report and review of the literature.
2008-11-05
Watchful waiting beats androgen deprivation therapy in early prostate cancer.
2008-11-05
Testosterone recovery after prolonged androgen suppression in patients with prostate cancer.
2008-10
FAF-Drugs2: free ADME/tox filtering tool to assist drug discovery and chemical biology projects.
2008-09-24
Analysis of overall survival in patients with nonmetastatic castration-resistant prostate cancer treated with vaccine, nilutamide, and combination therapy.
2008-07-15
Strategies for prostate cancer prevention: Review of the literature.
2008-07
Delayed dark adaptation caused by nilutamide.
2008-06
Antiandrogen withdrawal in castrate-refractory prostate cancer: a Southwest Oncology Group trial (SWOG 9426).
2008-06
Maximal androgen blockade for advanced prostate cancer.
2008-04
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008-04
Synthesis and structure-activity relationships of the first ferrocenyl-aryl-hydantoin derivatives of the nonsteroidal antiandrogen nilutamide.
2008-03-27
The androgen receptor can signal through Wnt/beta-Catenin in prostate cancer cells as an adaptation mechanism to castration levels of androgens.
2008-01-24
Androgen receptor functional analyses by high throughput imaging: determination of ligand, cell cycle, and mutation-specific effects.
2008
Role of vaccine therapy in cancer: biology and practice.
2007-12
Combined androgen blockade in advanced prostate cancer: looking back to move forward.
2007-09
A bifunctional colchicinoid that binds to the androgen receptor.
2007-08
A novel synthetic compound that interrupts androgen receptor signaling in human prostate cancer cells.
2007-07
Effects of steroidal and non-steroidal antiandrogens on wild-type and mutant androgen receptors.
2007-06-01
Long-term effectiveness of luteinizing hormone-releasing hormone agonist or antiandrogen monotherapy in elderly men with localized prostate cancer (T1-2): a retrospective study.
2007-03
Signaling pathway of nitric oxide production induced by ginsenoside Rb1 in human aortic endothelial cells: a possible involvement of androgen receptor.
2007-02-16
New therapeutic targets in the treatment of prostate cancer.
2007-01
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007-01
Antiandrogenic activity of pyrethroid pesticides and their metabolite in reporter gene assay.
2007-01
Ginsenoside Re, a main phytosterol of Panax ginseng, activates cardiac potassium channels via a nongenomic pathway of sex hormones.
2006-12
Bioactivation and hepatotoxicity of nitroaromatic drugs.
2006-10
[Keyrole of endocrinology in the victory against prostate cancer].
2006-09
Antiandrogen treatments in locally advanced prostate cancer: are they all the same?
2006-08
Maximal androgen blockade for the treatment of metastatic prostate cancer--a systematic review.
2006-06
Recent progress in hormonal therapy for advanced prostate cancer.
2006-05
Combined androgen blockade: an update.
2006-05
Role of 5 alpha-reductase inhibitors in the management of prostate cancer.
2006
Flare Associated with LHRH-Agonist Therapy.
2001
Androgen deprivation and other treatments for advanced prostate cancer.
2001
Patents

Patents

JP2003504306A
1
JP2011523657A
3
JPH04103573A
1
JPH059128A
1

Sample Use Guides

In Vivo Use Guide
The recommended dosage is 300 mg once a day for 30 days, followed thereafter by 150 mg once a day. Nilutamide Tablets can be taken with or without food.
Route of Administration: Oral
In Vitro Use Guide
At concentrations expected in the human liver (110 uM), nilutamide inhibited hexobarbital hydroxylase, benzphetamine N-demethylase, benzo(a)pyrene hydroxylase and 7-ethoxycoumarin O-deethylase activities by 85, 40, 35 and 25%, respectively in human liver microsomes.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:09:06 GMT 2025
Edited
by admin
on Mon Mar 31 18:09:06 GMT 2025
Record UNII
51G6I8B902
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NILANDRON
Preferred Name English
NILUTAMIDE
EP   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
nilutamide [INN]
Common Name English
NILUTAMIDE [ORANGE BOOK]
Common Name English
5,5-DIMETHYL-3-(.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-4-NITRO-M-TOLYL)HYDANTOIN
Systematic Name English
2,4-IMIDAZOLIDINEDIONE, 5,5-DIMETHYL-3-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)-
Systematic Name English
NILUTAMIDE [EP MONOGRAPH]
Common Name English
NILUTAMIDE [USP MONOGRAPH]
Common Name English
NILUTAMIDE [MI]
Common Name English
RU 23908
Code English
NILUTAMIDE [MART.]
Common Name English
NSC-758683
Code English
NILUTAMIDE [VANDF]
Common Name English
RU-23908
Code English
NILUTAMIDE [USP-RS]
Common Name English
Nilutamide [WHO-DD]
Common Name English
NILUTAMIDE [USAN]
Common Name English
Classification Tree Code System Code
LIVERTOX NBK548158
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
NDF-RT N0000000243
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
NCI_THESAURUS C146993
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
WHO-VATC QL02BB02
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
WHO-ATC L02BB02
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
NDF-RT N0000175560
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID3034165
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
MESH
C021277
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
NCI_THESAURUS
C1173
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
WIKIPEDIA
NILUTAMIDE
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
RS_ITEM_NUM
1463472
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
PUBCHEM
4493
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
SMS_ID
100000083883
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
NSC
758683
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
MERCK INDEX
m7899
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1274
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
EVMPD
SUB09291MIG
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
FDA UNII
51G6I8B902
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
DRUG BANK
DB00665
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
DAILYMED
51G6I8B902
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
USAN
HH-48
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
DRUG CENTRAL
1933
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
CAS
63612-50-0
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
CHEBI
7573
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
INN
5755
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
IUPHAR
2864
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY
RXCUI
31805
Created by admin on Mon Mar 31 18:09:06 GMT 2025 , Edited by admin on Mon Mar 31 18:09:06 GMT 2025
PRIMARY RxNorm
Related Record Type Details
Structure of N,N'-BIS(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)UREA
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 5-IMINONILUTAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-NITRO-3-TRIFLUOROMETHYLANILINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 3-OXONILUTAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of NILUTAMIDE
ACTIVE MOIETY
NIH
NCATS
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