Hydroxyflutamide

Hydroxyflutamide

Identifiers
IUPAC name 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
Synonyms	Hydroxyniphtholide, hydroxyniftolide; α,α,α-trifluoro-2-methyl-4'-nitro-m-lactotoluidide
CAS Number	52806-53-8
PubChem (CID)	91649
IUPHAR/BPS	2862
ChemSpider	82752
UNII	31D90UKP5Y
KEGG	C14204
ChEBI	CHEBI:43064
ChEMBL	CHEMBL491
ECHA InfoCard	100.169.708
Chemical and physical data
Formula	C11H11F3N2O4
Molar mass	292.21125 g/mol
3D model (Jmol)	Interactive image
SMILES CC(C)(C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F)O
InChI 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

Hydroxyflutamide (HF, OHF) (developmental code name SCH-16423), or 2-hydroxyflutamide, is a non-steroidal antiandrogen.^[1][2] It is the major active metabolite of flutamide.^[2] It is reported to possess an IC₅₀ of 700 nM for the androgen receptor (AR), about 4-fold less than that of bicalutamide.^[3]

See also

• Nilutamide
• Bicalutamide

References

1. Serra, C; Sandor, NL; Jang, H; Lee, D; Toraldo, G; Guarneri, T; Wong, S; Zhang, A; Guo, W; Jasuja, R; Bhasin, S (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): 4594–606. doi:10.1210/en.2013-1004. PMC 3836062. PMID 24105483.
2. Singh, Shankar; Gauthier, Sylvain; Labrie, Fernand (2000). "Androgen Receptor Antagonists (Antiandrogens) Structure-Activity Relationships". Current Medicinal Chemistry. 7 (2): 211–247. doi:10.2174/0929867003375371. ISSN 0929-8673.
3. Furr BJ (1995). "Casodex: preclinical studies and controversies". Annals of the New York Academy of Sciences. 761: 79–96. PMID 7625752.