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Merck

N8534

Nilutamide

solid

Synonym(s):

5,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedione, Anandron, RU-23908

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About This Item

Empirical Formula (Hill Notation):
C12H10F3N3O4
CAS Number:
63612-50-0
Molecular Weight:
317.22
NACRES:
NA.77
PubChem Substance ID:
24278596
UNSPSC Code:
51111800
MDL number:
MFCD00864670

Product Name

Nilutamide, solid

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)

SMILES string

CC1(C)NC(=O)N(c2ccc(c(c2)C(F)(F)F)[N+]([O-])=O)C1=O

InChI key

XWXYUMMDTVBTOU-UHFFFAOYSA-N

form

solid

originator

Sanofi Aventis

Quality Level

200

Gene Information

human ... AR(367)

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Application

Nilutamide has been used:
  • as a nuclear androgen receptor (nAR) inhibitor to study its effects on oocyte maturation in zebrafish
  • to determine its effects on bioluminescent Saccharomyces cerevisiae bioreporters in BLYAS assay
  • as a substrate in hydrogenation reaction

Biochem/physiol Actions

Nilutamide is a nuclear androgen receptor inhibitor. It is a nonsteroidal antiandrogen that competitively inhibits the binding of dihydrotestosterone to the androgen receptor. Nilutamide shows a therapeutic effect against prostate cancer.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H301,H360

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
057K1157
076K1722
076K1481
101K1091

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A Desai et al.
Urology, 58(6), 1016-1020 (2001-12-18)
To study the ability of nilutamide to induce prostate-specific antigen (PSA) responses in patients with hormone-resistant prostate cancer who had been exposed to prior antiandrogen therapy, because resistance to antiandrogens may be mediated by altered binding to a mutated or
Jing Yu et al.
Endocrinology, 151(4), 1822-1828 (2010-03-03)
The mechanisms of testosterone-induced vasodilatation are not fully understood. This study investigated the effect of testosterone on nitric oxide (NO) synthesis and its molecular mechanism using human aortic endothelial cells (HAEC). Testosterone at physiological concentrations (1-100 nm) induced a rapid
Richard Choo et al.
International journal of radiation oncology, biology, physics, 75(4), 983-989 (2009-05-05)
To determine the efficacy of a combined approach of radiotherapy (RT) plus 2-year androgen suppression (AS) as salvage treatment for prostate-specific antigen (PSA) relapse after radical prostatectomy (RP). Seventy-five patients with PSA relapse after RP were treated with salvage RT
Ravi A Madan et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 14(14), 4526-4531 (2008-07-17)
We reported previously the first randomized study of any kind in patients with nonmetastatic, castrate-resistant prostate cancer. The study employed vaccine, the hormone nilutamide, and the combined therapy (crossover for each arm) with an endpoint of time to progression. We
Urs A Boelsterli et al.
Current drug metabolism, 7(7), 715-727 (2006-11-01)
Certain drugs containing a nitroaromatic moiety (e.g., tolcapone, nimesulide, nilutamide, flutamide, nitrofurantoin) have been associated with organ-selective toxicity including rare cases of idiosyncratic liver injury. What they have in common is the potential for multistep nitroreductive bioactivation (6-electron transfer) that
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