| Iupac name | 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide |
|---|---|
| Width | 225px |
| Width 2 | 225px |
| Class | Nonsteroidal antiandrogen |
| Cas number | 52806-53-8 |
| Pubchem | 91649 |
| Iuphar ligand | 2862 |
| 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 | 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 | YPQLFJODEKMJEF-UHFFFAOYSA-N |
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]
References
- ^ Serra C, Sandor NL, Jang H, Lee D, Toraldo G, Guarneri T, Wong S, Zhang A, Guo W, Jasuja R, Bhasin S (December 2013). "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". Endocrinology. 154 (12): 4594–4606. doi:10.1210/en.2013-1004. PMC 3836062. PMID 24105483
- ^ Singh SM, Gauthier S, Labrie F (February 2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships". Current Medicinal Chemistry. 7 (2): 211–247. doi:10.2174/0929867003375371. PMID 10637363
- ^ Furr BJ (June 1995). "Casodex: preclinical studies and controversies". Annals of the New York Academy of Sciences. 761 (3): 79–96. Bibcode:1995NYASA.761...79F. doi:10.1111/j.1749-6632.1995.tb31371.x. PMID 7625752. S2CID 37242269