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CAS 36093-88-6

:

N-[4-[[(2,4-Diamino-1,4-dihydro-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid

Description:
N-[4-[[(2,4-Diamino-1,4-dihydro-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid, commonly known as methotrexate, is a potent antimetabolite and antifolate medication primarily used in the treatment of certain cancers and autoimmune diseases. This compound 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 benzoyl group, contributing to its biological activity. It is typically administered orally or via injection, and its pharmacokinetics can vary based on dosage and route of administration. The drug is known for its potential side effects, including myelosuppression, hepatotoxicity, and gastrointestinal disturbances, necessitating careful monitoring during treatment. Methotrexate's efficacy in various therapeutic regimens has made it a cornerstone in oncology and rheumatology, highlighting its significance in modern medicine.
Formula:C19H22N8O5
InChI:InChI=1S/C19H22N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,15,22H,5-7,20H2,(H,25,30)(H,28,29)(H,31,32)(H3,21,23,26,27)/t12-,15?/m0/s1
InChI key:InChIKey=SWIWRMRRLKUTKE-SFVWDYPZSA-N
SMILES:NC1C=2C(NC=C(CNC3=CC=C(C(N[C@@H](CCC(O)=O)C(O)=O)=O)C=C3)N2)=NC(N)=N1
Synonyms:
  • N-[4-[[(2,4-Diamino-1,4-dihydro-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid
  • L-Glutamic acid, N-[4-[[(2,4-diamino-1,4-dihydro-6-pteridinyl)methyl]amino]benzoyl]-
  • Quinoid 2,4-diaminodihydropteroylglutamic acid
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