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N8534

Sigma-Aldrich

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:
Molecular Weight:
317.22
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

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form

solid

Quality Level

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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PR0G000T3PR0G000S2PR0G000S1
manufacturer/tradename

Progard®

manufacturer/tradename

Progard®

manufacturer/tradename

Progard®

manufacturer/tradename

Progard®

feature

Optimal protection of Reverse Osmosis (RO) membrane, optimized system lifetime and performance. Removal of large particles, organic compounds and free chlorine from feed water with a silt density index (SDI) up to 12

feature

Optimal protection of RO membrane, optimized system lifetime and performance, feed water with a silt density index up to 5.

feature

Optimal protection of Reverse Osmosis (RO) membrane, optimized system lifetime and performance. Removal of large particles, organic compounds and free chlorine from feed water with a silt density index (SDI) up to 12.

feature

-

shipped in

ambient

shipped in

ambient

shipped in

ambient

shipped in

ambient

packaging

pkg of 1 unit

packaging

pkg of 1 unit

packaging

pkg of 1 unit

packaging

pkg of 1 unit

material

EPDM rubber

material

-

material

EPDM rubber , polypropylene

material

polypropylene (and EPDM)

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

Signal Word

Danger

Hazard Statements

Precautionary Statements

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
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
Kjetil Ask et al.
Biochemical pharmacology, 71(3), 377-385 (2005-11-30)
Nilutamide is a non-steroidal anti-androgen drug proposed in the treatment of metastatic prostatic carcinoma. Its therapeutic effects are overshadowed by the occurrence of adverse reactions, mediated by mechanisms that remain elusive. To elucidate possible mechanisms for nilutamide toxicity, we investigated
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

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