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Merck
CN

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
MDL number:
MFCD00864670
UNSPSC Code:
51111800
PubChem Substance ID:
24278596
NACRES:
NA.77

Key Documents

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form

solid

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

Signal Word

Danger

Hazard Statements

H301,H360

Precautionary Statements

P201 - P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1B

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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

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Masayasu Urushibara et al.
The Prostate, 67(8), 799-807 (2007-03-22)
Molecular basis for secondary antiandrogen therapy in prostate cancer with mutant androgen receptors (ARs) is not fully elucidated. Effects of steroidal and non-steroidal antiandrogens on transcriptional activities of wild-type and mutant (W741C, T877A, and W741C+T877A) ARs were measured. Crystal structure
Jennifer Keiser et al.
The Journal of antimicrobial chemotherapy, 65(9), 1991-1995 (2010-06-26)
The antischistosomal properties of the marketed antiandrogens bicalutamide, flutamide, nilutamide and cyproterone acetate were studied both in vivo and in vitro. Schistosoma mansoni-infected mice were treated orally with 50-400 mg/kg of the antiandrogens 3 and 7 weeks post-infection. In addition
Rajenahally V Jagadeesh et al.
Nature protocols, 10(4), 548-557 (2015-03-06)
In this protocol, we describe the preparation of nanoscale iron oxide-based materials and their use in the catalysis of different hydrogenation reactions. Pyrolysis of a Fe(OAc)2-phenanthroline complex on carbon at 800 °C under argon atmosphere results in the formation of
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
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
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