H4166
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:
Molecular Weight:
292.21
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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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
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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
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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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Our previous work has shown that an anti-androgen flutamide administered pre- and post-natally induced adverse effects on the epididymal morphology and function of adult boars. The present investigation is aimed to understand the effect of flutamide and its metabolite on
Seva E Kostrubsky et al.
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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
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