Hydroxyflutamide

{{short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

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| IUPAC_name = 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

| image = Hydroxyflutamide.svg

| width = 225px

| image2 = Hydroxyflutamide molecule ball.png

| width2 = 225px

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| class = Nonsteroidal antiandrogen

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| CAS_number_Ref =

| CAS_number = 52806-53-8

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| PubChem = 91649

| IUPHAR_ligand = 2862

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| ChemSpiderID_Ref =

| ChemSpiderID = 82752

| UNII = 31D90UKP5Y

| KEGG = C14204

| ChEBI = 43064

| ChEMBL = 491

| synonyms = 2-Hydroxyflutamide; HF; OHF; Flutamide-hydroxide; SCH-16423; Hydroxyniphtholide; Hydroxyniftolide; α,α,α-Trifluoro-2-methyl-4'-nitro-m-lactotoluidide

| C=11 | H=11 | F=3 | N=2 | O=4

| SMILES = CC(C)(C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F)O

| StdInChI_Ref =

| StdInChI = 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)

| StdInChIKey_Ref =

| StdInChIKey = YPQLFJODEKMJEF-UHFFFAOYSA-N

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Hydroxyflutamide (HF, OHF) (developmental code name SCH-16423), or 2-hydroxyflutamide, 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.{{cite journal | vauthors = Serra C, Sandor NL, Jang H, Lee D, Toraldo G, Guarneri T, Wong S, Zhang A, Guo W, Jasuja R, Bhasin S | display-authors = 6 | title = The effects of testosterone deprivation and supplementation on proteasomal and autophagy activity in the skeletal muscle of the male mouse: differential effects on high-androgen responder and low-androgen responder muscle groups | journal = Endocrinology | volume = 154 | issue = 12 | pages = 4594–4606 | date = December 2013 | pmid = 24105483 | pmc = 3836062 | doi = 10.1210/en.2013-1004 }}{{cite journal | vauthors = Singh SM, Gauthier S, Labrie F | title = Androgen receptor antagonists (antiandrogens): structure-activity relationships | journal = Current Medicinal Chemistry | volume = 7 | issue = 2 | pages = 211–247 | date = February 2000 | pmid = 10637363 | doi = 10.2174/0929867003375371 }} 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.{{cite journal | vauthors = Furr BJ | title = Casodex: preclinical studies and controversies | journal = Annals of the New York Academy of Sciences | volume = 761 | issue = 3 | pages = 79–96 | date = June 1995 | pmid = 7625752 | doi = 10.1111/j.1749-6632.1995.tb31371.x | s2cid = 37242269 | bibcode = 1995NYASA.761...79F }}

{{Affinities of selected androgen receptor ligands}}

{{Relative affinities of first-generation nonsteroidal antiandrogens for the androgen receptor}}

{{Relative potencies of selected antiandrogens in rats}}