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HomeProduct name listHYDROXYFLUTAMIDE

HYDROXYFLUTAMIDE

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

HYDROXYFLUTAMIDE Structural

What is HYDROXYFLUTAMIDE?

Description

2-hydroxy Flutamide is the major metabolite formed during the metabolism of the non-steroidal antiandrogen flutamide by cytochrome P450 (CYP) isoforms CYP1A2 and CYP3A4. Through competitive inhibition of the binding of testosterone to the nuclear androgen receptor (AR; IC50 = ~300-900), 2-hydroxy flutamide blocks the expression of AR target genes and prevents androgen-dependent stabilization of the AR. Compared to flutamide, 2-hydroxy flutamide is a more potent antiandrogen in vivo, demonstrating a higher binding affinity for the AR (0.1% binding affinity relative to dihydrotestosterone) and, thus, is the predominant contributor to the therapeutic effects of flutamide in the treatment of prostate cancer.

Chemical properties

HYDROXYFLUTAMIDE is Yellow-Brown Powder

The Uses of HYDROXYFLUTAMIDE

HYDROXYFLUTAMIDE is used non-steroidal antagonist Flutamide. Shown to be an antianhydrogen.

The Uses of HYDROXYFLUTAMIDE

Shown to be an antianhydrogen. The active metabolite of the widely used non-steroidal antagonist flutamide

The Uses of HYDROXYFLUTAMIDE

The active metabolite of the widely used non-steroidal antagonist Flutamide (F598850). Shown to be an antianhydrogen.

What are the applications of Application

2-Hydroxy-flutamide is an inhibitor of proliferation of estradiol-induced growth of MCF-7 breast cancer cells

Biochem/physiol Actions

Hydroxyflutamide plays a role in preventing the binding of 5α-dihydrotestosterone (DHT) and testosterone to the androgen receptors.

References

[1] kolvenbag g, furr b j a, blackledge g r p. receptor affinity and potency of non-steroidal antiandrogens: translation of preclinical findings into clinical activity[j]. prostate cancer and prostatic diseases, 1998, 1: 307-314.
[2] heinlein c a, chang c. androgen receptor in prostate cancer[j]. endocrine reviews, 2004, 25(2): 276-308.
[3] shet m s, mcphaul m, fisher c w, et al. metabolism of the antiandrogenic drug (flutamide) by human cyp1a2[j]. drug metabolism and disposition, 1997, 25(11): 1298-1303.
[4] gao w, kim j, dalton j t. pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands[j]. pharmaceutical research, 2006, 23(8): 1641-1658.

Properties of HYDROXYFLUTAMIDE

Melting point: 125-130°C
Boiling point: 443.8±45.0 °C(Predicted)
Density  1.472
storage temp.  room temp
solubility  DMSO: >10mg/mL
pka 12.87±0.70(Predicted)
form  powder
color  white to tan

Safety information for HYDROXYFLUTAMIDE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for HYDROXYFLUTAMIDE

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