Hydroxyflutamide

Hydroxyflutamide
Clinical data
Synonyms	2-Hydroxyflutamide; HF; OHF; Flutamide-hydroxide; SCH-16423; Hydroxyniphtholide; Hydroxyniftolide; α,α,α-Trifluoro-2-methyl-4'-nitro-m-lactotoluidide
Drug class	Nonsteroidal antiandrogen
Identifiers
	IUPAC name 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide;
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 (JSmol)	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 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 (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.
↑ 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. PMID 10637363.
↑ Furr BJ (1995). "Casodex: preclinical studies and controversies". Annals of the New York Academy of Sciences. 761: 79–96. doi:10.1111/j.1749-6632.1995.tb31371.x. PMID 7625752.
↑ Ayub M, Levell MJ (August 1989). "The effect of ketoconazole related imidazole drugs and antiandrogens on [3H] R 1881 binding to the prostatic androgen receptor and [3H]5 alpha-dihydrotestosterone and [3H]cortisol binding to plasma proteins". J. Steroid Biochem. 33 (2): 251–5. doi:10.1016/0022-4731(89)90301-4. PMID 2788775.

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