ContaminantDB: Nilutamide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:16:24 UTC

Update Date

2026-05-14 16:45:30 UTC

Accession Number

CHEM003740

Identification

Common Name

Nilutamide

Class

Small Molecule

Description

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.

Contaminant Sources

HMDB Contaminants - Urine
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Androgen Antagonist
Antineoplastic Agent
Drug
Human Neurotoxin
Metabolite
Organic Compound
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,5-Dimethyl-3-(alpha,alpha,alpha-trifluoro-4-nitro-m-tolyl)hydantoin	ChEBI
Nilandron	ChEBI
Nilutamida	ChEBI
Nilutamidum	ChEBI
5,5-Dimethyl-3-(a,a,a-trifluoro-4-nitro-m-tolyl)hydantoin	Generator
5,5-Dimethyl-3-(α,α,α-trifluoro-4-nitro-m-tolyl)hydantoin	Generator
5,5-Dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)- 2,4-imidazolidinedione	HMDB
Hoechst brand OF nilutamide	HMDB
Aventis behring brand OF nilutamide	HMDB
Aventis brand OF nilutamide	HMDB
Anandron	HMDB

Chemical Formula

C₁₂H₁₀F₃N₃O₄

Average Molecular Mass

317.221 g/mol

Monoisotopic Mass

317.062 g/mol

CAS Registry Number

63612-50-0

IUPAC Name

5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione

Traditional Name

nilutamide

SMILES

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

InChI Identifier

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)

InChI Key

XWXYUMMDTVBTOU-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Phenylhydantoins

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:7573 )
imidazolidinone (CHEBI:7573 )
(trifluoromethyl)benzenes (CHEBI:7573 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	4.19e-03 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	1.74	ALOGPS
logP	2.25	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	15.01	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	95.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.23 m³·mol⁻¹	ChemAxon
Polarizability	25.88 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-9051000000-b212093377487cffc158	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0600-0094000000-0991ece9f9d42b94c643	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-014i-0019000000-7989a507a8031f03f612	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00di-0090000000-1d63c70e06fcd4c6d922	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0kmi-0390000000-05fc687a7f642e06e60a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0kmi-0390000000-e2d42b542bf6dc07d5c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0zfr-1970000000-f1091bfdddddc602902c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0lz9-1920000000-14b04987997234218267	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-f4acafe069c7fdcf8fc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9025000000-2c79c0bbfc87dd118bd7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-a91f0e83aff94e2bad18	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-19746ba07e5113297e15	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-4009000000-f2904499b324cc347c22	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-740d06c64bdf821f7e3d	Spectrum

Toxicity Profile

Route of Exposure

Rapidly and completely absorbed, yielding high and persistent plasma concentrations.

Mechanism of Toxicity

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.

Metabolism

The 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 Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For 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 Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include dizziness, general discomfort, headache, nausea, and vomiting.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID