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

• ChemBase ID: 547
• Molecular Formular: C12H10F3N3O4
• Molecular Mass: 317.2207096
• Monoisotopic Mass: 317.06234048
• SMILES: FC(F)(F)c1cc(N2C(=O)C(NC2=O)(C)C)ccc1[N+](=O)[O-]
• Canonical SMILES: O=C1NC(C(=O)N1c1ccc(c(c1)C(F)(F)F)[N+](=O)[O-])(C)C
• InChI: 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)
• InChIKey: XWXYUMMDTVBTOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
• IUPAC Traditional name: nilutamide; 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
• Brand Name: Anandron; Nilandron; Nilandrone; Nilutamida [Spanish]; Nilutamide [Usan:Ban:Inn]; Nilutamidum [Latin]
• Synonyms: Nilutamide; 5,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedion; 1-3-Trifluoromethyl-4-nitrophenyl)-4,4-dimethylimidazoline-2,5-dione; Nilandron; Nilandrone; RU 23908; RU 23908-10; 5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)-2,4-imidazolidinedione; 5,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedione; Anandron; RU-23908; Nilutamide

Database IDs

• CAS Number: 63612-50-0
• MDL Number: MFCD00864670
• PubChem SID: 160964010; 46505381; 24278596
• PubChem CID: 4493

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.008641
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.2507768
• LogD (pH = 7.4): 2.2507768
• Log P: 2.2507768
• Molar Refractivity: 67.2218 cm^3
• Polarizability: 24.620682 Å^3
• Polar Surface Area: 92.55 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.74
• LOG S: -4.88
• Solubility (Water): 4.19e-03 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Pale Yellow Solid; solid
• Melting Point: 153-154°C
• Hydrophobicity(logP): 1.8

Safety Information

• Storage Condition: Refrigerator
• RTECS: NI9453300
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 60-25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H360
• GHS Precautionary statements: P201-P301 + P310-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... AR(367)
• Mechanism of Action: Androgen receptor blocker, preventing its interaction with testosterone

Product Information

• Purity: 97%
• Application(s): Antineoplastic agent; Used for treatment of prostatic cancer
• Empirical Formula (Hill Notation): C12H10F3N3O4

DETAILS

DrugBank - DB00665

• Drug Groups: approved
• 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.
• Indication: For use in combination with surgical castration for the treatment of metastatic prostate cancer involving distant lymph nodes, bone, or visceral organs (Stage D2).
• Pharmacology: 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.
• Toxicity: Symptoms of overdose include dizziness, general discomfort, headache, nausea, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Absorption: Rapidly and completely absorbed, yielding high and persistent plasma concentrations.
• Half Life: 38.0-59.1 hours
• 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.
• References: 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. [Pubmed] ; 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. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - N8534

Biochem/physiol Actions
Nilutamide is an antiandrogen used in the treatment of prostate cancer.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N8534.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - N467500

Nonsteroidal antiandrogen. Antineoplastic (hormonal).

REFERENCES

• 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. Pubmed
• 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. Pubmed
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