Methotrexate, MP Biomedicals™

Description

Acts as a folic acid antagonist. Methotrexate, MP Biomedicals is a mix of 4-amino-10-methylfolic acid and related compounds, structurally similar to folic acid. A potent anticancer agent, it blocks DNA synthesis by blocking production of tetrahydrofolate

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.

• Potent inhibitor of dihydrofolate reductase in DHFR-based protein expression systems
• Anti-cancer agent used in antitumor studies
• Effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites
• 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: 10 mg
• 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