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Product Details:

  • Product Name: Methotrexate
  • CAS #: 59-05-2
  • 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:

    Hepatic.

  • Toxicity:

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

  • IUPAC: (2S)-2-[(4-{[(2, 4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid
  • ATC: L01BA01 L04AX03
  • PubChem: 126941
  • DrugBank: DB00563 (APRD00353)
  • Formula: C19H24O2
  • Molecular Mass: 454.4393
  • Synonyms: Amethopterin Amethopterine HDMTX L-Amethopterin Methopterin Methotextrate Methotrexat Methotrexate Sodium Methylaminopterin Methylaminopterinum MTX N-Bismethylpteroylglutamic Acid
  • SMILES: CN(CC1=CN=C2N=C(N)N=C(N)C2=N1)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O
  • AHFS Code: 10:00.0
  • InChl: FBOZXECLQNJBKD-ZDUSSCGKSA-N
  • 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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LGM Pharma Acquires CDMO

On July 27, 2020, LGM Pharma announced its acquisition of the formulation development and drug product contract manufacturing business of Nexgen Pharma, Inc. As a result, you will notice our new logo and visuals throughout the website. We’re working on updates to reflect the exciting, expanded CDMO capabilities and services we now can offer you.

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