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Product Details:

  • Product Name: Methotrexate Disodium
  • CAS #: 7413-34-5
  • Mode of Action:

    Methotrexate anti-tumor activity is a result of the inhibition of folic acid reductase, leading to inhibition of DNA synthesis and inhibition of cellular replication. The mechanism involved in its activity against rheumatoid arthritis is not known.

  • Pharmacodynamics:

    Methotrexate is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Methotrexate inhibits folic acid reductase which is responsible for the conversion of folic acid to tetrahydrofolic acid. At two stages in the biosynthesis of purines and at one stage in the synthesis of pyrimidines, one-carbon transfer reactions occur which require specific coenzymes synthesized in the cell from tetrahydrofolic acid. Tetrahydrofolic acid itself is synthesized in the cell from folic acid with the help of an enzyme, folic acid reductase. Methotrexate looks a lot like folic acid to the enzyme, so it binds to it quite strongly and inhibits the enzyme. Thus, DNA synthesis cannot proceed because the coenzymes needed for one-carbon transfer reactions are not produced from tetrahydrofolic acid because there is no tetrahydrofolic acid. Methotrexate selectively affects the most rapidly dividing cells (neoplastic and psoriatic cells). Methotrexate is also indicated in the management of severe, active, classical, or definite rheumatoid arthritis.

  • Metabolism:

    Methotrexate undergoes hepatic and intracellular metabolism to polyglutamated forms which can be converted back to methotrexate by hydroxylase enzymes. These polyglutamates act as inhibitors of dihydrofolate reductase and thymidylate synthetase. A small amount of metabolism to 7-hydroxymethotrexate may occur at doses commonly prescribed. Furthermore, intestinal flora partially metabolizes methotrexate after oral administration.

  • Toxicity:

    Symptoms of overdose include bone marrow suppression and gastrointestinal toxicity. LD50=43mg/kg(orally in rat).

  • IUPAC: Disodium N-(4-(((2, 4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-L-glutamate Glutamic acid, N-(p-(((2, 4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-, disodium salt, L-(+)-
  • ATC: L01BA01" L04AX03
  • PubChem: 126941
  • DrugBank: DB00563
  • Formula: C20-H20-N8-O5.2Na, C20-H22-N8-O5.2Na
  • Molecular Mass: 498.409
  • Synonyms: 4-Amino-N(sup 10)-methylpteroylglutamic acid disodium salt, Abitrexate, Amethopterin sodium, Disodium methotrexate, EINECS 231-022-0, Farmitrexat, Folex, Folex PFS, Ledertrexate, Methotrexat dinatrium, Methotrexate disodium salt, Methotrexate LPF, Methotrexate preservative free, Methotrexate sodium, Methotrexate sodium preservative free, Mexate, Mexate-AQ, Mexate-AQ preserved, MTX disodium, Sodium methotrexate, Trexall, UNII-3IG1E710ZN
  • SMILES: c12c(ncc(n1)CN(c1ccc(C(N[C@@H](CCC(=O)[O-])C(=O)[O-])=O)cc1)C)nc(N)nc2N.[Na+].[Na+]
  • AHFS Code: 10:00.0
  • InChl: 1S/C20H22N8O5.2Na/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);;/q;2*+1/p-2/t13-;;/m0../s1
  • General Reference:

    1. Klareskog L, van der Heijde D, de Jager JP, Gough A, Kalden J, Malaise M, Martin Mola E, Pavelka K, Sany J, Settas L, Wajdula J, Pedersen R, Fatenejad S, Sanda M: Therapeutic effect of the combination of etanercept and methotrexate compared with each treatment alone in patients with rheumatoid arthritis: double-blind randomised controlled trial. Lancet. 2004 Feb 28;363(9410):675-81. Pubmed
    2. Johnston A, Gudjonsson JE, Sigmundsdottir H, Ludviksson BR, Valdimarsson H: The anti-inflammatory action of methotrexate is not mediated by lymphocyte apoptosis, but by the suppression of activation and adhesion molecules. Clin Immunol. 2005 Feb;114(2):154-63. Pubmed

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