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MilliporeSigma

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

Key Documents

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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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This Item
Y0000829F93971463472
Nilutamide solid

Sigma-Aldrich

N8534

Nilutamide

vibrant-m

Y0000829

Nilutamide

Flutamide

Sigma-Aldrich

F9397

Flutamide

USP

USP

1463472

Nilutamide

form

solid

form

-

form

-

form

-

Quality Level

200

Quality Level

-

Quality Level

100

Quality Level

-

originator

Sanofi Aventis

originator

-

originator

Schering Plough

originator

-

Gene Information

human ... AR(367)

Gene Information

human ... AR(367)

Gene Information

human ... AR(367)
mouse ... Ar(11835)
rat ... Ar(24208)

Gene Information

-

Application

Nilutamide has been used:
  • as a nuclear androgen receptor (nAR) inhibitor to study its effects on oocyte maturation in zebrafish[1]
  • to determine its effects on bioluminescent Saccharomyces cerevisiae bioreporters in BLYAS assay[2]
  • as a substrate in hydrogenation reaction[3]

Biochem/physiol Actions

Nilutamide is a nuclear androgen receptor inhibitor.[1] It is a nonsteroidal antiandrogen that competitively inhibits the binding of dihydrotestosterone to the androgen receptor.[4] Nilutamide shows a therapeutic effect against prostate cancer.[5]

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
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
Chang-Xi Bai et al.
Circulation, 112(12), 1701-1710 (2005-09-15)
Women have longer QTc intervals than men and are at greater risk for arrhythmias associated with long QTc intervals, such as drug-induced torsade de pointes. Recent clinical and experimental data suggest an important role of testosterone in sex-related differences in
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
Chih-Yang Chang et al.
Fertility and sterility, 85 Suppl 1, 1195-1203 (2006-04-18)
To investigate the effects of androgen and antiandrogen and the expression of androgen receptor on mouse embryonic stem cells (ESCs) and the inner cell mass. Controlled laboratory study. Academic university hospital. Blastocysts from mice developed at the Institute for Cancer
View All Related Papers

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