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    Flutamide (SCH 13521)
    Flutamide (SCH 13521)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1764
    CAS #: 13311-84-7Purity ≥98%

    Description: Flutamide (also known as SCH13521; SCH-13521; trade names: Flucinom; Flugerel; Niftolid; Flutan; Oncosal etc.), a toluidine derivative, is a potent non-steroidal antiandrogen drug (AR antagonist) with potential anticancer activity. It is mainly used for the treatment of prostate cancer. Flutamide can be transformed into an active metablolite that binds to androgen receptor with a Ki value of 55 nM. Flutamideis a toluidine derivative and nonsteroidal antiandrogen that is structurally related to bicalutamide and nilutamide. Flutamide and the more active metabolite 2-hydroxyflutamide competitively block dihydrotestosterone binding at androgen receptors, forming inactive complexes which cannot translocate into the cell nucleus. 

    References: Mol Cell Endocrinol. 1986 Mar;44(3):261-70; J Steroid Biochem. 1988 Jun;29(6):691-8.

    Related CAS#: 52806-53-8 (2-Hydroxyflutamide)

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    Molecular Weight (MW)276.21
    FormulaC11H11F3N2O3
    CAS No.13311-84-7
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 55 mg/mL (199.1 mM)
    Water: <1 mg/mL
    Ethanol: 55 mg/mL (199.1 mM)
    Other infoChemical Name: N-(4-nitro-3-(trifluoromethyl)phenyl)isobutyramide
    InChi Key: MKXKFYHWDHIYRV-UHFFFAOYSA-N
    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)
    SMILES Code: CC(C)C(NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1)=O 
    SynonymsSCH-13521; SCH13521; SCH 13521; trade names: Flucinom; Flugerel; Niftolid; Flutan; Oncosal; Profamid; Prostacur; Flutaplex; Fugerel; Grisetin; Eulexin; Apimid; Chimax; Drogenil; Euflex; Eulexine; Flucinome; Fluken; Flulem; Flutabene; Flutacan; FlutaGry; Flutamex; Flutamin; Prostadirex; Prostica; Prostogenat; Tafenil; Tecnoflut; Testotard. FLUT.


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    In Vitro

    In vitro activity: Flutamide (Eulexin) is an antiandrogen drug. Flutamide-OH, the active metabolite of flutamide, directly binds at rat anterior pituitary androgen receptor with Ki values of 55 nM. Flutamide does not affect the proliferation of an androgen-sensitive clone of the mouse mammary carcinoma Shionogi SC-l 15 cells in culture, shows only antiandrogenic effect, but not androgenic effect. Flutamide provides treatment for prostate cancer when used along with leuprolide.


    Kinase Assay: Aliquots of 100 μl cytosol are incubated at 0-4°C for 18 h with 100 μl of the indicated saturating concentration of [3H]T in the presence or absence of increasing concentrations of nonlabeled T, DHT, flutamide (FLU) or flutamide-OH (FLU-OH). At the end of the incubation, free and bound T are separated by the addition of 200 μl dextran-coated charcoal (1 % charcoal, 0.1% dextran T-70, 0.1% gelatin, 1.5 mM EDTA and 50 mM Tris (pH 7.4)) for 15 min before centrifugation at 2300 × g for another 15 min at 0-4°C. Aliquots (350 μl) of the supernatant are transferred to scintillation vials with 10 ml of an aqueous counting solution before counting in a Beckman LS 330 counter.


    Cell Assay: Effect of flutamide on the growth of an androgen-sensitive clone (SEM-l) of mouse mammary carcinoma Shionogi cells in culture. The cells are incubated up to 40 days in medium (MEM + 2% dextran-coated charcoal extracted fetal calf serum) containing the compounds at a concentration of 1 μM. Media are changed every second day.

    In VivoFlutamide causes a markedly reduction in rat ventral prostate weight from 319 mg to 245 mg. A combination of flutamide and LHRH agonist induces an additive effect with a decrease in prostate weight to 101 mg, and an marked drop in prostatic ODC activity.
    Animal modelMale rat
    Formulation & DosageDissolved in 1% gelatin-9% NaCl; 5 mg/kg; s.c. injection
    References

    Mol Cell Endocrinol. 1986 Mar;44(3):261-70; J Steroid Biochem. 1988 Jun;29(6):691-8.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

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