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    TAK-700/Orteronel (s-isomer)
    TAK-700/Orteronel (s-isomer)

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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 #: V0819
    CAS #: 566939-85-3 Purity ≥98%

    Description: Orterone (aslo known as TAK-700; TAK 700; TAK700) is an orally bioavailable non-steroidal androgen synthesis inhibitor of human 17,20-lyase inhibitor with potential anticancer activity. It inhibits human 17,20-lyase with IC50 of 38 nM, and exhibits >1000-fold selectivity for human 17,20-lyase over other CYPs (e.g. 11-hydroxylase and CYP3A4). It is a novel hormonal therapy developed by Takeda company for the treatment of prostate cancer.

    References: Bioorg Med Chem. 2011 Nov 1;19(21):6383-99; J Steroid Biochem Mol Biol. 2012 Apr;129(3-5):115-28.

    Related CAS: 566939-85-3 (s-isomer); 426219-18-3 (racemic)

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    Molecular Weight (MW)307.35
    FormulaC18H17N3O2
    CAS No.566939-85-3 (s-isomer)
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 61 mg/mL (198.5 mM)
    Water:<1 mg/mL
    Ethanol: 8 mg/mL (26.0 mM)
    Solubility (In vivo)0.5% methylcellulose: 30 mg/mL  
    SynonymsTAK700; TAK-700; TAK 700; Orteronel (s-isomer); 

    Chemical Name: (S)-6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide

    InChi Key: OZPFIJIOIVJZMN-SFHVURJKSA-N

    InChi Code: InChI=1S/C18H17N3O2/c1-19-17(22)14-3-2-13-9-15(5-4-12(13)8-14)18(23)6-7-21-11-20-10-16(18)21/h2-5,8-11,23H,6-7H2,1H3,(H,19,22)/t18-/m0/s1

    SMILES Code: O=C(NC)C1=CC=C2C=C([[email protected]@]3(O)CCN4C=NC=C43)C=CC2=C1           


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    In Vitro

    In vitro activity: In vitro, TAK-700 shows the potent inhibitory activity against rat and human steroid 17,20-lyase with IC50 of 54 nM and 38 nM, respectively. While other CYP isoforms including 11-hydroxylase and CYP3A4 are not significantly affected by TAK-700. In microsomes expressing human CYP isoforms, TAK-700 exhibit greater inhibitory effects on 17,20-lyase with IC50 of 19 nM compared to the other CYP isoforms. TAK-700 shows the inhibitory activity against monkey 17,20-lyase and 17-hydroxylase with IC50 of 27 nM and 38 nM, respectively. In monkey adrenal cells, TAK-700 inhibits the ACTH stimulated production of DHEA and androstenedione with IC50 of 110 nM and 130 nM, respectively. Moreover, TAK-700 also potently inhibits DHEA production in human adrenocortical tumor line H295R cells with IC50 of 37 nM.


    Kinase Assay: Rat 11-hydroxylase activity is measured according to a method described for side-chain cleavage activity previously with some modifications. The reaction mixture contained 200 mM mannitol, 4.5 mM HEPES, 2.3 mM potassium phosphate (pH 7.4), 0.1 mM EDTA·2 K, 0.03% BSA (crystallized), 4.5 mM NADPH, 11 mM calcium chloride, 4 μg of mitochondria protein, 10 nM [1,2-3H]-hydroxy-11-deoxycorticosterone (11-deoxycortisol) (NEN, dissolved in 0.02% Tween-80), and 1-1000 nM test compounds in a total volume of 150 μL. The concentrations of reagents are expressed as the final concentration in the reaction mixture. The test compounds are serially diluted with dimethylformamide, and 1.5 μL is added directly to the reaction mixture. After 30 min incubation at 37°C the reaction is terminated by addition of 400 μL of ethyl acetate and 100 μL of distilled water, then vortexed for 30 s and briefly centrifuged. Three hundred μLs of the organic phase is transferred to a new tube and evaporated until dry using nitrogen gas. The steroids are dissolved with 30 μL of ethyl acetate and the whole volume is applied to silica gel TLC plates. The substrate and the products (11-deoxycortisol and cortisol) are separated in the toluene-acetone (7:2) solvent system.


    Cell Assay: In monkey adrenal cells, orteronel inhibits the ACTH stimulated production of DHEA and androstenedione with IC50 of 110 nM and 130 nM, respectively. Moreover, Orteronel also potently inhibits DHEA production in human adrenocortical tumor line H295R cells with IC50 of 37 nM. In vitro, orteronel shows the potent inhibitory activity against rat and human steroid 17,20-lyase with IC50 of 54 nM and 38 nM, respectively. While other CYP isoforms including 11-hydroxylase and CYP3A4 are not significantly affected by Orteronel. In microsomes expressing human CYP isoforms, Orteronel exhibit greater inhibitory effects on 17,20-lyase with IC50 of 19 nM compared to the other CYP isoforms.

    In VivoIn cynomolgus monkeys, oral treatment of TAK-700 at a dose of 1 mg/kg markedly reduces serum testosterone and dehydroepiandrosterone (DHEA) levels. Oral treatment of TAK-700 at a dose of 1 mg/kg results in favorable pharmacokinetic parameters with Tmax, Cmax, t1/2 and AUC0-24 hours of 1.7 hours, 0.147 μg/mL, 3.8 hours and 0.727 μg h/mL, respectively.
    Animal modelAdult male cynomolgus monkeys. 
    Formulation & DosageDissolved in 0.5% methylcellulose; ≤1 mg/kg; Oral gavage
    ReferencesBioorg Med Chem. 2011 Nov 1;19(21):6383-99; J Steroid Biochem Mol Biol. 2012 Apr;129(3-5):115-28.


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

    TAK-700 (Orteronel)

    Bioorg Med Chem. 2011 Nov 1;19(21):6383-99.
     

    TAK-700 (Orteronel)


    J Steroid Biochem Mol Biol. 2012 Apr;129(3-5):115-28.
     

    TAK-700 (Orteronel)

    J Steroid Biochem Mol Biol. 2012 Apr;129(3-5):115-28.


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