Methotrexate, MP Biomedicals™

Description

Acts as a potent anti-cancer agent. Methotrexate, MP Biomedicals is a folic acid antagonist that is structurally similar to folic acid. It is a mixture of 4-amino-10-methylfolic acid and related compounds. It is a potent inhibitor of dihydrofolate reducta

Blocks DNA synthesis by blocking the production of tetrahydrofolate cofactors required for the synthesis of thymidine. Methotrexate is actively transported into cells by the folate transporter. In the cell, it is converted to a high molecular weight polyglutamate metabolite by folypolyglutamate synthase that, in turn, binds to dihydrofolate reductase and inhibits its activity. Methotrexate-polyglutamate is degraded intracellularly by gamma-glutamyl hydrolase.

Methotrexate is an allosteric inhibititor of dihydrofolate reductase (DHFR), the enzyme that catalyzes the conversion of dihydrofolate to tetrahydrofolate. Since tetrahydrolfolate is required for purine and pyrimidine synthesis, methotrexate treatment results in the inhibition of DNA and RNA synthesis.

• A potent inhibitor of dihydrofolate reductase and is an agent for antitumor studies
• Used to inhibit dihydrofolate reductase in DHFR-based protein expression systems
• Effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites
• Also shows immunosuppressive effects, e.g., in rheumatoid arthritis

Specifications

Chemical Identifiers

• CAS: 59-05-2
• Molecular Formula: C20H22N8O5
• Molecular Weight (g/mol): 454.447
• InChI Key: FBOZXECLQNJBKD-ZDUSSCGKSA-N
• Synonym: methotrexate, abitrexate, rheumatrex, amethopterin, mexate, metatrexan, hdmtx, trexall, methylaminopterinum, antifolan
• PubChem CID: 126941
• ChEBI: CHEBI:44185
• IUPAC Name: (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
• SMILES: CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O

• Melting Point: 185°C to 204°C
• Boiling Point: 184°C to 204°C (monohydrate decomposition)
• Quantity: 1 g
• Solubility Information: Soluble in alkaline solutions with decomposition. Insoluble in water, ethanol, chloroform and ether.
• Optical Rotation: 19–24°
• Formula Weight: 454.4
• Grade: USP
• Physical Form: Powder

Safety and Handling

Recommended Storage

+4°C

WARNING: Reproductive Harm - www.P65Warnings.ca.gov