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H4166

Sigma-Aldrich

Hydroxyflutamide

≥98% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C11H11F3N2O4
CAS Number:
52806-53-8
Molecular Weight:
292.21
MDL number:
MFCD00563126
UNSPSC Code:
51111800
PubChem Substance ID:
329815208
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to tan

solubility

DMSO: >10 mg/mL

originator

Schering Plough

storage temp.

room temp

SMILES string

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)

InChI key

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.

Biochem/physiol Actions

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.

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Tomonori Ishikawa et al.
Reproduction (Cambridge, England), 133(6), 1233-1239 (2007-07-20)
Androgen receptor (AR) is reported to be expressed in human uterine endometrium, but not much information is available on the role of androgens in human endometrium. The purpose of this study is to investigate the role of androgens in the
G E Jensen et al.
SAR and QSAR in environmental research, 22(1-2), 35-49 (2011-03-11)
Three modelling systems (MultiCase®, LeadScope® and MDL® QSAR) were used for construction of androgenic receptor antagonist models. There were 923-942 chemicals in the training sets. The models were cross-validated (leave-groups-out) with concordances of 77-81%, specificity of 78-91% and sensitivity of
Renate Louw-du Toit et al.
Biochemical and biophysical research communications, 491(1), 140-146 (2017-07-18)
Progestins used in endocrine therapies bind to multiple steroid receptors and are associated with several side-effects. It is thus important to understand the relationship between steroid receptor cross-reactivity and the side-effect profile of progestins. In cell lines that express negligible
Anticancer Drugs That Modulate Hormone Action
Medicinal Chemistry of Anticancer Drugs, 81-131 (2015)
Brenda Bingham et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 36(7), 1433-1443 (2011-03-18)
The posterior bed nuclei of the stria terminalis (BST) are important neural substrate for relaying limbic influences to the paraventricular nucleus (PVN) of the hypothalamus to inhibit hypothalamic-pituitary-adrenal (HPA) axis responses to emotional stress. Androgen receptor-expressing cells within the posterior
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