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Record Information
Version1.0
Creation Date2014-09-11 05:16:24 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003740
Identification
Common NameNilutamide
ClassSmall Molecule
DescriptionNilutamide 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Androgen Antagonist
  • Antineoplastic Agent
  • Drug
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
5,5-Dimethyl-3-(alpha,alpha,alpha-trifluoro-4-nitro-m-tolyl)hydantoinChEBI
NilandronChEBI
NilutamidaChEBI
NilutamidumChEBI
5,5-Dimethyl-3-(a,a,a-trifluoro-4-nitro-m-tolyl)hydantoinGenerator
5,5-Dimethyl-3-(α,α,α-trifluoro-4-nitro-m-tolyl)hydantoinGenerator
5,5-Dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)- 2,4-imidazolidinedioneHMDB
Hoechst brand OF nilutamideHMDB
Aventis behring brand OF nilutamideHMDB
Aventis brand OF nilutamideHMDB
AnandronHMDB
Chemical FormulaC12H10F3N3O4
Average Molecular Mass317.221 g/mol
Monoisotopic Mass317.062 g/mol
CAS Registry Number63612-50-0
IUPAC Name5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
Traditional Namenilutamide
SMILESCC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F
InChI IdentifierInChI=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)
InChI KeyXWXYUMMDTVBTOU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentPhenylhydantoins
Alternative Parents
Substituents
  • 3-phenylhydantoin
  • Phenylimidazolidine
  • Alpha-amino acid or derivatives
  • Trifluoromethylbenzene
  • Nitrobenzene
  • Nitroaromatic compound
  • N-acyl urea
  • Ureide
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboximide
  • Organic nitro compound
  • C-nitro compound
  • Carbonic acid derivative
  • Urea
  • Azacycle
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Carbonyl group
  • Organohalogen compound
  • Organic zwitterion
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alkyl fluoride
  • Organic nitrogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Alkyl halide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility4.19e-03 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.0042 g/LALOGPS
logP1.74ALOGPS
logP2.25ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)15.01ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area95.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.23 m³·mol⁻¹ChemAxon
Polarizability25.88 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0a59-9051000000-b212093377487cffc158View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-f4acafe069c7fdcf8fc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9025000000-2c79c0bbfc87dd118bd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-a91f0e83aff94e2bad18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-19746ba07e5113297e15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-4009000000-f2904499b324cc347c22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-740d06c64bdf821f7e3dView in MoNA
Toxicity Profile
Route of ExposureRapidly and completely absorbed, yielding high and persistent plasma concentrations.
Mechanism of ToxicityNilutamide 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.
MetabolismThe results of a human metabolism study using 14C-radiolabelled tablets show that nilutamide is extensively metabolized and less than 2% of the drug is excreted unchanged in urine after 5 days. Route of Elimination: Nilutamide is extensively metabolized andless than 2% of the drug is excreted unchanged in urine after 5 days. Fecal elimination is negligible, ranging from 1.4% to 7% of the dose after 4 to 5 days. Half Life: 38.0-59.1 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor use in combination with surgical castration for the treatment of metastatic prostate cancer involving distant lymph nodes, bone, or visceral organs (Stage D2).
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include dizziness, general discomfort, headache, nausea, and vomiting.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00665
HMDB IDHMDB0014803
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNilutamide
Chemspider ID4337
ChEBI ID7573
PubChem Compound ID4493
Kegg Compound IDC08164
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kassouf W, Tanguay S, Aprikian AG: Nilutamide as second line hormone therapy for prostate cancer after androgen ablation fails. J Urol. 2003 May;169(5):1742-4.
2. Lukka H, Waldron T, Klotz L, Winquist E, Trachtenberg J: Maximal androgen blockade for the treatment of metastatic prostate cancer--a systematic review. Curr Oncol. 2006 Jun;13(3):81-93.