| Identification | Back Directory | [Name]
HYDROXYFLUTAMIDE | [CAS]
52806-53-8 | [Synonyms]
Sch-16423
Hydroxyflutamid
HYDROXYFLUTAMIDE
5-HYDROXYFLUTAMIDE
hydroxyniphtholide
2-HYDROXY-FLUTAMIDE
Hydroxyflutamide, >=98%
HydroxyflutaMide (Hydroxyniphtholide)
Hydroxy-Flutamide(Flutamide metabolite)
a,a,a-Trifluoro-2-methyl-4′-nitro-m-lactotoluidide
α,α,α-Trifluoro-2-Methyl-4'-nitro-M-
lactotoluidide
N-[3-(Trifluoromethyl)-4-nitrophenyl]-2-hydroxyisobutyramide
alpha,alpha,alpha-Trifluoro-2-methyl-4'-nitro-m-lactotoluidide
2-Hydroxy-2-methyl-N-(3-trifluoromethyl-4-nitrophenyl)propanamide
2-hydroxy-2-methyl-n-(4-nitro-3-(trifluoromethyl)phenyl)-propanamid
2-HYDROXY-2-METHYL-N-[4-NITRO-3-(TRIFLUOROMETHYL)PHENYL]-PROPANAMIDE
2-Hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propionamide
Propanamide, 2-hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)-
5-Hydroxyflutamide, 2-Hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-propanamide,
HYDROXYFLUTAMIDE (2-HYDROXY-2-METHYL-N-{4''-NITRO-3''-(TRIFLUOROMETHYL)PHENYL}PROPANAMIDE) | [Molecular Formula]
C11H11F3N2O4 | [MDL Number]
MFCD00563126 | [MOL File]
52806-53-8.mol | [Molecular Weight]
292.21 |
| Chemical Properties | Back Directory | [Appearance]
Yellow-Brown Powder | [Melting point ]
125-130°C | [Boiling point ]
443.8±45.0 °C(Predicted) | [density ]
1.472 | [storage temp. ]
-20°C Freezer | [solubility ]
DMSO: >10mg/mL | [form ]
powder | [pka]
12.87±0.70(Predicted) | [color ]
white to tan |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow-Brown Powder | [Uses]
Shown to be an antianhydrogen. The active metabolite of the widely used non-steroidal antagonist flutamide | [Uses]
The active metabolite of the widely used non-steroidal antagonist Flutamide (F598850). Shown to be an antianhydrogen. | [Uses]
The active metabolite of the widely used non-steroidal antagonist Flutamide. Shown to be an antianhydrogen. | [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 CYP3A4.1 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.2 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.3 | [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. |
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