CAS 63612-50-0|Nilandrone|RU 23908|Nilutamide|5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione|1-3-Trifluoromethyl-4-nitrophenyl)-4,4-dimethylimidazoline-2,5-dione|Nilandron...

General Information

Structure

Molecular Formula

C₁₂H₁₀F₃N₃O₄

Molecular Mass

317.2207096

Exact Mass

317.06234048

Charge

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

Canonic Smiles

O=C1NC(C(=O)N1c1ccc(c(c1)C(F)(F)F)[N+](=O)[O-])(C)C

Isomeric Smiles

FC(F)(F)c1cc(N2C(=O)C(NC2=O)(C)C)ccc1[N+](=O)[O-]

Calculated Properties

JChem

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

Polarizability

24.620682

Polar Surface Area

92.55

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

1.74

LOG S

-4.88

Solubility (Water)

4.19e-03 g/l

Data Source

Names and Identifiers

IUPAC name

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

Synonyms

1-3-Trifluoromethyl-4-nitrophenyl)-4,4-dimethylimidazoline-2,5-dioneRU 23908NilutamideNilandroneRU 23908-10Nilandron5,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedionAnandron5,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedioneNilutamideRU-239085,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)-2,4-imidazolidinedione

IUPAC Traditional name

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

Brand Name

AnandronNilutamida [Spanish]NilandronNilandroneNilutamide [Usan:Ban:Inn]Nilutamidum [Latin]

Names and Identifiers

Registration numbers

CAS Number

63612-50-0

PubChem SID

4650538124278596160964010

PubChem CID

4493

MDL Number

MFCD00864670

Registration numbers

Properties

Safety Information

2811

P201-P301+P310-P308+P313

NI9453300

36/37/39-45

Pharmacology Properties

human ... AR(367)

Androgen receptor blocker, preventing its interaction with testosterone

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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

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]

TRC

N467500

Nonsteroidal antiandrogen. Antineoplastic (hormonal).

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.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

• Raynaud, J.-P., et al.: J. Steroid Biochem., 11, 93 (1979)

• Harris, M.G., et al.: Drugs Aging, 3, 9 (1979)

• Decensi, A. et al., Eur. J. Cancer, 1991, 27, 1100, (clin trial)

• Harris, M.G. et al., Drugs Aging, 1993, 3, 9, (rev)

• Moguilewsky, M. et al., J. Steroid Biochem., 1987, 27, 871, (rev, pharmacol)

• Ojasoo, T., Drugs of the Future, 1987, 12, 763, (rev)

• Raynaud, J.P. et al., Prog. Clin. Biol. Res., 1985, 185A, 99, (rev, pharmacol)

• Moguilewsky, M. et al., Prog. Cancer Res. Ther., 1988, 35, 349, (rev, activity)

• Ger. Pat., 1977, Roussel, 2 649 925; CA, 87, 85005, (synth)

• Dhar, J.D. et al., Contraception, 1990, 42, 121, (tox)

• Gomez, J.-L. et al., Am. J. Med., 1992, 92, 563, (tox)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 496

• Berson, A. et al., J. Pharmacol. Exp. Ther., 1994, 270, 167, (tox)

• Pendyala, L. et al., Cancer Chemother. Pharmacol., 1988, 22, 69, (metab)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

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

Synonyms

IUPAC Traditional name

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

Brand Name

AnandronNilutamida [Spanish]NilandronNilandroneNilutamide [Usan:Ban:Inn]Nilutamidum [Latin]

Registration numbers

CAS Number

63612-50-0

PubChem SID

4650538124278596160964010

PubChem CID

4493

MDL Number

MFCD00864670

References

PubChem Literature

From Data Sources

• 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

• 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

• Raynaud, J.-P., et al.: J. Steroid Biochem., 11, 93 (1979)

• Harris, M.G., et al.: Drugs Aging, 3, 9 (1979)

• Decensi, A. et al., Eur. J. Cancer, 1991, 27, 1100, (clin trial)

• Harris, M.G. et al., Drugs Aging, 1993, 3, 9, (rev)

• Moguilewsky, M. et al., J. Steroid Biochem., 1987, 27, 871, (rev, pharmacol)

• Ojasoo, T., Drugs of the Future, 1987, 12, 763, (rev)

• Raynaud, J.P. et al., Prog. Clin. Biol. Res., 1985, 185A, 99, (rev, pharmacol)

• Moguilewsky, M. et al., Prog. Cancer Res. Ther., 1988, 35, 349, (rev, activity)

• Ger. Pat., 1977, Roussel, 2 649 925; CA, 87, 85005, (synth)

• Dhar, J.D. et al., Contraception, 1990, 42, 121, (tox)

• Gomez, J.-L. et al., Am. J. Med., 1992, 92, 563, (tox)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 496

• Berson, A. et al., J. Pharmacol. Exp. Ther., 1994, 270, 167, (tox)

• Pendyala, L. et al., Cancer Chemother. Pharmacol., 1988, 22, 69, (metab)

Bioactivity

PubChem BioAssay

Properties

Safety Information

2811

P201-P301+P310-P308+P313

NI9453300

36/37/39-45

Pharmacology Properties

human ... AR(367)

Androgen receptor blocker, preventing its interaction with testosterone

Molecule Details

DrugBank

DB00665

Drug Groups

approved

Description

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

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]

TRC

N467500

Nonsteroidal antiandrogen. Antineoplastic (hormonal).

Sigma Aldrich

N8534

Molecule

ID:547