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H4166

Sigma-Aldrich

Hydroxyflutamide

≥98% (HPLC)

Synonyme(s) :

2-Hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-propanamide, 2-Hydroxyflutamide, Hydroxyniphtholide, Sch 16423, a,a,a-Trifluoro-2-methyl-4′-nitro-m-lactotoluidide

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About This Item

Formule empirique (notation de Hill) :
C11H11F3N2O4
Numéro CAS:
52806-53-8
Poids moléculaire :
292.21
Numéro MDL:
MFCD00563126
Code UNSPSC :
51111800
ID de substance PubChem :
329815208
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Essai

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to tan

Solubilité

DMSO: >10 mg/mL

Auteur

Schering Plough

Température de stockage

room temp

Chaîne SMILES 

CC(C)(O)C(=O)Nc1ccc(c(c1)C(F)(F)F)[N+]([O-])=O

InChI

1S/C11H11F3N2O4/c1-10(2,18)9(17)15-6-3-4-8(16(19)20)7(5-6)11(12,13)14/h3-5,18H,1-2H3,(H,15,17)

Clé InChI

YPQLFJODEKMJEF-UHFFFAOYSA-N

Application

Hydroxyflutamide has been used:
  • as an androgen receptor antagonist to study its effects on cardiomyocyte hypertrophy induced by dihydrtestosterone (DHT) in primary neonatal rat ventricular cardiomyocyte and rat cardio myoblast (H9c2) cells.
  • as an androgen receptor antagonist for the treatment of MDA-kb2 cells to check its effect on luciferase expression.
  • as an antagonist control in transcriptional activation assay.

Actions biochimiques/physiologiques

Hydroxflutamide is an AR (androgen receptor) antagonist.
Hydroxflutamide is an AR antagonist. Androgen receptors (ARs) are nuclear hormone receptors/transcription factors. Hydroxyflutamide is an androgen antagonist with publications going back to 1981. It is one of a few gold standard AR antagonists; activities of new antagonists are measured against hydroxyflutamide.
Hydroxyflutamide plays a role in preventing the binding of 5α-dihydrotestosterone (DHT) and testosterone to the androgen receptors.

Caractéristiques et avantages

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 Schering Plough. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000421418
0000421418
0000186818
0000186817
0000152947

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Chemical research in toxicology, 20(10), 1503-1512 (2007-09-29)
Treatment with flutamide has been associated with clinical hepatotoxicty. The toxicity, metabolism,and transport of flutamide were investigated using cultured human hepatocytes. Flutamide and its major metabolite, 2-hydroxyflutamide, caused an inhibition of taurocholate efflux in human hepatocytes with an IC50=75 microM
Jennifer C Brennan et al.
Toxicology in vitro : an international journal published in association with BIBRA, 47, 18-25 (2017-11-07)
There is a need to adapt cell bioassays to 384-well and 1536-well formats instead of the traditional 96-well format as high-throughput screening (HTS) demands increase. However, the sensitivity and performance of the bioassay must be re-verified in these higher micro-well
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Biochemical pharmacology, 82(11), 1651-1662 (2011-09-13)
Prostate cancer (PCa) progression is enhanced by androgen and treatment with antiandrogens represents an alternative to castration. While patients initially respond favorably to androgen ablation therapy, most experience a relapse of the disease within 1-2 years by expressing androgen receptor
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