Product Name

Nilutamide

CAS Number

63612-50-0

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Product Name:
Nilutamide
CAS Number:
63612-50-0
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).
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.

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.

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.

IUPAC:
5, 5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2, 4-dione
ATC:
L02BB02
PubChem:
4493
DrugBank:
DB00665 (APRD00150)
Formula:
C20H24N2O6
Molecular Mass:
317.2207
SMILES:
CC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F
AHFS Code:
10:00.0
InChi:
XWXYUMMDTVBTOU-UHFFFAOYSA-N
General Reference:
General Reference:

  1. 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
  2. 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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