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Merck
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Documentos clave

N8534

Sigma-Aldrich

Nilutamide

solid

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C12H10F3N3O4
Número de CAS:
63612-50-0
Peso molecular:
317.22
MDL number:
MFCD00864670
UNSPSC Code:
51111800
PubChem Substance ID:
24278596
NACRES:
NA.77

form

solid

Quality Level

200

originator

Sanofi Aventis

SMILES string

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

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)

InChI key

XWXYUMMDTVBTOU-UHFFFAOYSA-N

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_germany

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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Certificados de análisis (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
Hong Sun et al.
Chemosphere, 66(3), 474-479 (2006-07-22)
Many pesticides possess hormonal activity and have thus been classified as endocrine disruptors. Pyrethroids are commonly used pesticides worldwide, but little has been done to characterize their antiandrogenic activity potential. We tested three frequently encountered pyrethroids (fenvalerate, cypermethrin, permethrin) and
Jing Yu et al.
Biochemical and biophysical research communications, 353(3), 764-769 (2007-01-02)
Ginsenosides have been shown to stimulate nitric oxide (NO) production in aortic endothelial cells. However, the signaling pathways involved have not been well studied in human aortic endothelial cells. The present study was designed to examine whether purified ginsenoside Rb1
Hideki Koizumi et al.
FEBS letters, 584(11), 2440-2444 (2010-04-27)
Icariin, a flavonoid isolated from Epimedii herba, stimulated phosphorylation of endothelial nitric oxide synthase (eNOS) at Ser1177, Akt (Ser473) and ERK1/2 (Thr202/Tyr204). The icariin-induced eNOS phosphorylation was abolished by an androgen receptor (AR) antagonist, nilutamide in human umbilical vein endothelial
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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