An androgen receptor antagonist and a prodrug form of 2-hydroxy flutamide
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Active Metabolite(s)
152712-hydroxy Flutamide
Labeled Version(s)
33541Flutamide-d7
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Flutamide

Item No. 20359

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-propanamide
CAS Number
13311-84-7
Synonyms
  • Niftolide
  • NSC 147834
  • NSC 251876
  • SCH 13521
Molecular Formula
C11H11F3N2O3
Formula Weight
276.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
226, 294 nm
SMILES
O=C(C(C)C)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1
InChi Code
InChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)
InChi Key
MKXKFYHWDHIYRV-UHFFFAOYSA-N
Shipping & Storage Information
Storage
Room temperature
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $36

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    5 g

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    10 g

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    25 g

    $294

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    Cayman Chemical
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    Product Description

    Flutamide is an androgen receptor antagonist (Kis = 1.3 and 7.5 µM for the cytosolic rat ventral prostate and anterior pituitary receptors, respectively) and a prodrug form of 2-hydroxy flutamide (Item No. 15271).1 Flutamide is converted to 2-hydroxy flutamide by the cytochrome P450 (CYP) isoform CYP1A2 in human liver microsomes.1 It is cytotoxic to PC3 and LNCaP prostate cancer cells with IC50 values of 98.8 and 81.8 µM, respectively.2 Flutamide (50 mg/kg per day) reduces tumor growth in a PC-82 mouse xenograft model.3 Formulations containing flutamide have been used in the treatment of prostate cancer.

    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. Shi, Q., Wada, K., Ohkoshi, E., et al. Antitumor agents 290. Design, synthesis, and biological evaluation of new LNCaP and PC-3 cytotoxic curcumin analogs conjugated with anti-androgens. Bioorg. Med. Chem. 20(13), 4020-4031 (2012).

    3. Nnane, I.P., Long, B.J., Ling, Y.Z., et al. Anti-tumour effects and pharmacokinetic profile of 17-(5'-isoxazolyl)androsta-4,16-dien-3-one (L-39) in mice: An inhibitor of androgen synthesis. Br. J. Cancer 83(1), 74-82 (2000).