Nilutamide

CAS No:
63612-50-0 Category:
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Product Details:

  • CAS No: 63612-50-0
  • AHFC code: 10:00.0
  • Synonyms:
  • ATC Code: L02BB02
  • Chemical Formula: C20H24N2O6
  • Molecular Weight: 317.2207
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00665 (APRD00150)
  • SMILES: CC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F
  • InChl: XWXYUMMDTVBTOU-UHFFFAOYSA-N
  • PubChem: 4493
  • IUPAC: 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione

Additional Details

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).
Pharmacodynamics:
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.
Mode of Action:
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.
Toxicity:
Symptoms of overdose include dizziness, general discomfort, headache, nausea, and vomiting.
General Reference:
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 cancerãa systematic review. Curr Oncol. 2006 Jun;13(3):81-93. Pubmed
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