Compound ID | 3274

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Sulfametoxydiazine

Synonym(s): sulfameter  |  5-methoxysulfadiazine

Class: Sulfa drug / Sulphonamide

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Active against Streptococcus pyogenes, Streptococcus pneumoniae, Escherichia coli, Salmonella typhimurium, and Klebsiella pneumoniae; sulphonamides are structural analogues of p-aminobenzoic acid and act as competitive inhibitors (and alternate substrates) of dihydropteroate synthase (DHPS) to block the synthesis of folic acid. Primarily bacteriostatic; rapid emergence of resistance
Description: Synthetic compound (sulfa/ sulphonamide drug); sulfanilamide derivative (structural analogue of p-aminobenzoic acid); long-acting (~7 days)
Year first mentioned: 1962
Development status: Experimental
Chemical structure(s):
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Molecular weight: 280.3
Iso. SMILES: COC1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI Key: GPTONYMQFTZPKC-UHFFFAOYSA-N
Can. SMILES: COC1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI: InChI=1S/C11H12N4O3S/c1-18-9-6-13-11(14-7-9)15-19(16,17)10-4-2-8(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5326
Guide to Pharmacology: sulfametoxydiazine
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/14296029/
  • https://ascpt.onlinelibrary.wiley.com/doi/10.1002/cpt196563316

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