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    InvivoChem Cat #: V0847
    CAS #: 59-05-2Purity ≥98%

    Description: Methotrexate (MTX; alphamethopterin; amethopterin; methylaminopterin; CL-14377; NCIC04671; WR19039; NCI-C04671) is an FDA approved antineoplastic and immunosuppressant drug that belongs to the antimetabolite and antifolate class of drugs. It acts by inhibiting the metabolism of folic acid in activated peripheral T cells. Specifically, methotrexate binds to and inhibits the enzyme dihydrofolate reductase, resulting in inhibition of purine nucleotide and thymidylate synthesis and, subsequently, inhibition of DNA and RNA syntheses. Methotrexate (Amethopterin) is the disease-modifying antirheumatic drug (DMARD) of first choice for the treatment of RA in most countries worldwide. Methotrexate is an antineoplastic agent used to fight a number of different cancers, such as acute lymphoblastic leukemia and solid cancers.

    References: J Clin Invest. 1998 Jul 15;102(2):322-8; J Clin Invest. 1993 Dec;92(6):2675-82.

    Related CAS #: 7413-34-5 (disodium)  59-05-2 (free acid)  7532-09-4 (monosodium)   6745-93-3 (hydrate)   15475-56-6 (sodium)                                                    

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    Molecular Weight (MW)454.44
    CAS No.59-05-2
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 90 mg/mL (198.0 mM)
    Water: <1 mg/mL
    Ethanol: <1 mg/mL
    Solubility (In vivo)2% DMSO+30% PEG 300+5% Tween 80+ddH2O: 5 mg/mL
    Synonymsalphamethopterin; amethopterin; methylaminopterin; CL 14377; NCIC04671; WR19039; WR-19039; WR 19039; MTX; NCI-C04671; NCI C04671; CL14377; CL-14377; Methotrexate.

    Chemical Name: (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioic acid.


    InChi Code: InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1

    SMILES Code: O=C(O)[[email protected]@H](NC(C1=CC=C(N(CC2=NC3=C(N)N=C(N)N=C3N=C2)C)C=C1)=O)CCC(O)=O           

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    In Vitro

    In vitro activity: Methotrexate (0.1-10 mM) induces apoptosis of in vitro activated T cells from human peripheral blood. Methotrexate achieves clonal deletion of activated T cells in mixed lymphocyte reactions. Methotrexate can selectively delete activated peripheral blood T cells by a CD95-independent pathway. Methotrexate is taken up by cells via the reduced folate carrier and then is converted within the cells to polyglutamates. Methotrexate leads to diminished production of leukotriene B4 by neutrophils stimulated ex vivo. Methotrexate polyglutamates inhibit the enzyme aminoimidazolecarboxamidoadenosineribonucleotide (AICAR) transformylase more potently than the other enzymes involved in purine biosynthesis. Methotrexate is also known to suppress TNF activity by suppressing TNF-induced nuclear factor-κB activation in vitro, in part related to a reduction in the degradation and inactivation of an inhibitor of this factor, IκBα, and probably related to the release of adenosine. Methotrexate suppresses the production of both TNF and IFN-γ by T-cell-receptor-primed T lymphocytes from both healthy human donors and RA patients. Methotrexate treatment is associated with a significant decrease of TNF-α-positive CD4+ T cells, while the number of T cells expressing the anti-inflammatory cytokine IL-10 increased.

    Cell Assay: Each cell line is studied in growth inhibition experiments using 96-well microtiter plates. As antifols are schedule dependent, preliminary experiments are aimed at defining the longest duration of exposure that would allow for continuous logarithmic phase growth of cells without changing of the culture media while maintaining a linear relationship between SRB optical density and cell number. Twenty-four hours after cell plating, the cell lines are exposed to the antifol for 120 h (three replicates per experiment). To ensure that a complete sigmoidal survival-concentration curve could be observed, the following drug concentrations are studied: Methotrexate (0.002-5 μM), AMT (0.0001-1 μM), PXD (0.0003-10 μM), TLX (0.0002-0.5 μM). Experiments are repeated at least twice.

    In VivoMethotrexate increases splenocyte AICAR content, raised adenosine concentrations in exudates from carrageenan-inflamed air pouches, and markedly inhibits leukocyte accumulation in inflamed air pouches in mice. Methotrexate-mediated reduction in leukocyte accumulation is partially reversed by injection of adenosine deaminase (ADA) into the air pouch, completely reverses by a specific adenosine A2 receptor antagonist, 3,7-dimethyl-1-propargylxanthine (DMPX), but not affected by an adenosine A1 receptor antagonist, 8-cyclopentyl-dipropylxanthine in mice.
    Animal modelMice
    Formulation & DosageThe combination of bioactive phytochemicals is administered one week prior to the Methotrexate exposure. Treatment group I: mice are given a combination of green tea polyphenols and eleutherosides from Siberian ginseng (0.2 mL/10 g, i.g. once daily) for 15 days, and a single dose of Methotrexate (2 mg/kg, i.p. once daily) is added on the 8th day. Treatment group II: mice are given a combination of grape seed proanthocyanidins and eleutherosides from Siberian ginseng for 15 days, and Methotrexate is administered on the 8th day in a similar manner. Model group: animals received distilled water instead of bioactive phytochemicals combinations for 15 days and the same Methotrexate protocol applied to this group on the 8th day. Control group: mice are given distilled water through 15 days and physiological saline instead of Methotrexate is administered on the 8th day in a similar manner. Twelve hours after the final doses, the animals are euthanized by cervical dislocation.

    J Clin Invest. 1998 Jul 15;102(2):322-8; J Clin Invest. 1993 Dec;92(6):2675-82.

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


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