Hydroxyflutamide

Chemical compound From Wikipedia, the free encyclopedia

Hydroxyflutamide (developmental code SCH-16423; also known as 2-hydroxyflutamide, HF, and OHF) is a nonsteroidal antiandrogen (NSAA) and the major active metabolite of flutamide, which is considered to be a prodrug of hydroxyflutamide as the active form.[1][2] It has been reported to possess an IC50 of 700 nM for the androgen receptor (AR), which is about 4-fold less than that of bicalutamide.[3]

More information Compound, RBATooltip Relative binding affinity ...
Affinities[a][4]
Compound RBATooltip Relative binding affinity[b]
Metribolone 100
Dihydrotestosterone 85
Cyproterone acetate 7.8
Bicalutamide 1.4
Nilutamide 0.9
Hydroxyflutamide 0.57
Flutamide <0.0057
Notes:
  1. [a]
    At androgen receptors; measured in human prostate tissue.
  2. [b]
    Relative to Metribolone, which is by definition 100%
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Other names2-Hydroxyflutamide; HF; OHF; Flutamide-hydroxide; SCH-16423; Hydroxyniphtholide; Hydroxyniftolide; α,α,α-Trifluoro-2-methyl-4'-nitro-m-lactotoluidide
Drug classNonsteroidal antiandrogen
CAS Number
PubChem CID
Quick facts Clinical data, Other names ...
Hydroxyflutamide
Clinical data
Other names2-Hydroxyflutamide; HF; OHF; Flutamide-hydroxide; SCH-16423; Hydroxyniphtholide; Hydroxyniftolide; α,α,α-Trifluoro-2-methyl-4'-nitro-m-lactotoluidide
Drug classNonsteroidal antiandrogen
Identifiers
  • 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.169.708 Edit this at Wikidata
Chemical and physical data
FormulaC11H11F3N2O4
Molar mass292.214 g·mol−1
3D model (JSmol)
  • CC(C)(C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F)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)
  • Key:YPQLFJODEKMJEF-UHFFFAOYSA-N
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More information Species, IC50Tooltip Half maximal inhibitory concentration (nM) ...
Relative affinities of first-generation nonsteroidal antiandrogens for the androgen receptor
SpeciesIC50Tooltip Half maximal inhibitory concentration (nM)RBATooltip Relative binding affinity (ratio)
Bicalutamide2-HydroxyflutamideNilutamideBica / 2-OH-fluBica / niluRef
Rat190700ND4.0ND[5]
Rat~400~900~9002.32.3[6]
RatNDNDND3.3ND[7]
Rata35954565186201.35.2[8]
Human~300~700~5002.51.6[9]
Human~100~300ND~3.0ND[10]
Humana2490234553001.02.1[8]
Footnotes: a = Controversial data. Sources: See template.
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More information Antiandrogen, Relative potency ...
Relative potencies of selected antiandrogens
AntiandrogenRelative potency
Bicalutamide4.3
Hydroxyflutamide3.5
Flutamide3.3
Cyproterone acetate1.0
Zanoterone0.4
Description: Relative potencies of orally administered antiandrogens in antagonizing 0.8 to 1.0 mg/kg s.c.Tooltip subcutaneous injection testosterone propionate-induced ventral prostate weight increase in castrated immature male rats. Higher values mean greater potency. Sources: See template.
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References

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