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
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.169.708
Chemical and physical data
Formula C11H11F3N2O4
Molar mass 292.21125 g/mol
3D model (JSmol)

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]

Hydroxyflutamide and other
ligands at the AR[4][5]
CompoundRBA (%)
Metribolone100
Dihydrotestosterone85
Cyproterone acetate7.8
Spironolactone2.3
Bicalutamide1.4
Nilutamide0.9
Hydroxyflutamide0.57
Flutamide<0.0057

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. PMID 10637363.
  3. 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.
  4. 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.
  5. Yamasaki K, Sawaki M, Noda S, Muroi T, Takakura S, Mitoma H, Sakamoto S, Nakai M, Yakabe Y (2004). "Comparison of the Hershberger assay and androgen receptor binding assay of twelve chemicals". Toxicology. 195 (2-3): 177–86. doi:10.1016/j.tox.2003.09.012. PMID 14751673.


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