An active metabolite of the antiandrogen flutamide
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Pro-drug Form(s)
20359Flutamide
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2-hydroxy Flutamide

Item No. 15271

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-propanamide
CAS Number
52806-53-8
Synonyms
  • Hydroxyniphtholide
  • SCH 16423
Molecular Formula
C11H11F3N2O4
Formula Weight
292.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 25 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
225, 291 nm
SMILES
O=C(C(O)(C)C)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1
InChi Code
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)
InChi Key
YPQLFJODEKMJEF-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    50 mg

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    Product Description

    2-hydroxy Flutamide is the major metabolite formed during the metabolism of the non-steroidal antiandrogen flutamide by cytochrome P450 (CYP) isoforms CYP1A2 and CYP3A4.1 Through competitive inhibition of the binding of testosterone to the nuclear androgen receptor (AR; IC50 = ~300-900), 2-hydroxy flutamide blocks the expression of AR target genes and prevents androgen-dependent stabilization of the AR.2 Compared to flutamide, 2-hydroxy flutamide is a more potent antiandrogen in vivo, demonstrating a higher binding affinity for the AR (0.1% binding affinity relative to dihydrotestosterone) and, thus, is the predominant contributor to the therapeutic effects of flutamide in the treatment of prostate cancer.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shet, M.S., McPhaul, M., Fisher, C.W., et al. Metabolism of the antiandrogenic drug (flutamide) by human CYP1A2. Drug Metab. Dispos. 25(11), 1298-1303 (1997).

    2. Kolvenbag, G.J.C.M., Furr, B.J.A., and Blackledge, G.R.P. Receptor affinity and potency of non-steroidal antiandrogens: Translation of preclinical findings into clinical activity. Prostate Cancer Prostatic Dis. 1(6), 307-314 (1998).

    3. Gao, W., Kim, J., and Dalton, J.T. Pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands. Pharmacol. Res. 23(8), 1641-1658 (2006).