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CAS 134-05-4

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N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl](formyl)amino}phenyl)carbonyl]-L-glutamic acid

Description:
N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl](formyl)amino}phenyl)carbonyl]-L-glutamic acid, commonly known as Methotrexate, is a potent antimetabolite and antifolate drug primarily used in the treatment of certain cancers and autoimmune diseases. It functions by inhibiting dihydrofolate reductase, an enzyme critical for DNA synthesis and cell replication, thereby impeding the growth of rapidly dividing cells. Methotrexate is characterized by its complex structure, which includes a pteridine ring, an amino acid moiety, and a carboxylic acid group, contributing to its solubility and biological activity. The compound exhibits a range of pharmacokinetic properties, including absorption, distribution, metabolism, and excretion that can vary based on dosage and administration route. Its therapeutic effects are often accompanied by side effects, necessitating careful monitoring during treatment. Methotrexate is also utilized in lower doses for chronic inflammatory conditions, showcasing its versatility in medical applications.
Formula:C20H19N7O7
InChI:InChI=1/C20H19N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,7,9,13H,5-6,8H2,(H,24,31)(H,29,30)(H,33,34)(H3,21,22,25,26,32)/t13-/m0/s1
InChI key:UGWUWNVTCLDEOG-ZDUSSCGKSA-N
SMILES:c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)N(Cc1cnc2c(c(nc(=N)[nH]2)O)n1)C=O
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