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63612-50-0 molecular structure
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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 and InChIs

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

Cite this record

CBID:547 http://www.chembase.cn/molecule-547.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
IUPAC Traditional name
5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
nilutamide
Brand Name
Anandron
Nilandron
Nilandrone
Nilutamida [Spanish]
Nilutamide [Usan:Ban:Inn]
Nilutamidum [Latin]
Synonyms
5,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedione
Anandron
RU-23908
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
Nilutamide
CAS Number
63612-50-0
MDL Number
MFCD00864670
PubChem SID
24278596
46505381
160964010
PubChem CID
4493

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 15.008641  H Acceptors
H Donor LogD (pH = 5.5) 2.2507768 
LogD (pH = 7.4) 2.2507768  Log P 2.2507768 
Molar Refractivity 67.2218 cm3 Polarizability 24.620682 Å3
Polar Surface Area 92.55 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.74  LOG S -4.88 
Solubility (Water) 4.19e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Dichloromethane expand Show data source
Methanol expand Show data source
Apperance
Pale Yellow Solid expand Show data source
solid expand Show data source
Melting Point
153-154°C expand Show data source
Hydrophobicity(logP)
1.8 expand Show data source
Storage Condition
Refrigerator expand Show data source
RTECS
NI9453300 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
60-25 expand Show data source
Safety Statements
36/37/39-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H360 expand Show data source
GHS Precautionary statements
P201-P301 + P310-P308 + P313 expand Show data source
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 expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Gene Information
human ... AR(367) expand Show data source
Mechanism of Action
Androgen receptor blocker, preventing its interaction with testosterone expand Show data source
Purity
97% expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antineoplastic agent expand Show data source
Used for treatment of prostatic cancer expand Show data source
Empirical Formula (Hill Notation)
C12H10F3N3O4 expand Show data source

DETAILS

DETAILS

TRC TRC DrugBank DrugBank Sigma Aldrich Sigma Aldrich
Toronto Research Chemicals - N467500 external link
Nonsteroidal antiandrogen. Antineoplastic (hormonal).
DrugBank - DB00665 external link
Item Information
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 external link
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.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Ger. Pat., 1977, Roussel, 2 649 925; CA, 87, 85005, (synth)
  • • Raynaud, J.P. et al., Prog. Clin. Biol. Res., 1985, 185A, 99, (rev, pharmacol)
  • • Ojasoo, T., Drugs of the Future, 1987, 12, 763, (rev)
  • • Moguilewsky, M. et al., J. Steroid Biochem., 1987, 27, 871, (rev, pharmacol)
  • • Pendyala, L. et al., Cancer Chemother. Pharmacol., 1988, 22, 69, (metab)
  • • Moguilewsky, M. et al., Prog. Cancer Res. Ther., 1988, 35, 349, (rev, activity)
  • • Dhar, J.D. et al., Contraception, 1990, 42, 121, (tox)
  • • Decensi, A. et al., Eur. J. Cancer, 1991, 27, 1100, (clin trial)
  • • Gomez, J.-L. et al., Am. J. Med., 1992, 92, 563, (tox)
  • • Harris, M.G. et al., Drugs Aging, 1993, 3, 9, (rev)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 496
  • • Berson, A. et al., J. Pharmacol. Exp. Ther., 1994, 270, 167, (tox)
  • • 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
  • • Raynaud, J.-P., et al.: J. Steroid Biochem., 11, 93 (1979)
  • • Harris, M.G., et al.: Drugs Aging, 3, 9 (1979)
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PATENTS

PATENTS

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INTERNET

INTERNET

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