Nilutamide

Nilutamide (INN, USAN, BAN)

Clinical data
Pronunciation	nye-LOO-tah-mide
Trade names	Nilandron, Anandron
AHFS/Drugs.com	Monograph
MedlinePlus	a697044
Pregnancy category	US: C
Routes of administration	Oral
ATC code	L02BB02 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Good
Protein binding	80–84%
Metabolism	Liver: CYP2C19, FMO
Metabolites	At least 5, some active
Biological half-life	23–87 hours (mean 56 hours, or about 2 days)
Excretion	Urine (62%); Feces (<10%)
Identifiers
IUPAC name 5,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
Synonyms	RU-23908
CAS Number	63612-50-0 Y
PubChem (CID)	4493
IUPHAR/BPS	2864
DrugBank	DB00665 Y
ChemSpider	4337 Y
UNII	51G6I8B902 Y
KEGG	D00965 Y
ChEBI	CHEBI:7573 Y
ChEMBL	CHEMBL1274 Y
ECHA InfoCard	100.153.268
Chemical and physical data
Formula	C12H10F3N3O4
Molar mass	317.221 g/mol
3D model (Jmol)	Interactive image
SMILES O=C2N(c1ccc([N+]([O-])=O)c(c1)C(F)(F)F)C(=O)C(N2)(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) Y Key:XWXYUMMDTVBTOU-UHFFFAOYSA-N Y

Nilutamide (brand names Nilandron (US), Anandron (CA)) is a synthetic, non-steroidal antiandrogen (NSAA) used in the treatment of advanced-stage (metastatic) prostate cancer. It was developed by Roussel, first introduced in 1987 (in Europe) and was the second NSAA to be marketed, with flutamide preceding it and bicalutamide following it in 1995. It was not introduced until 1996 in the United States.[1] Because most prostate cancer cells rely on activation of the androgen receptor (AR) for growth and survival, nilutamide can slow the progression of the disease and extend life in men with prostate cancer.

Nilutamide shows unique and unfavorable tolerability and toxicity profiles, most importantly a high incidence of interstitial pneumonitis (which can progress to pulmonary fibrosis, a potentially fatal condition), and this has limited its clinical use. From a safety standpoint, bicalutamide is clinically preferred not only over nilutamide (due primarily to its risk of interstitial pneumonitis) but also flutamide (due to its high risk of hepatotoxicity) in choice of NSAA.

Nilutamide is used in prostate cancer in combination with a gonadotropin-releasing hormone (GnRH) analogue at a dosage of 300 mg/day (150 mg twice daily) for the first 4 weeks of treatment, and 150 mg/day thereafter. It is not indicated as a monotherapy in prostate cancer.