Compound ID | 2069

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Sulfamethoxazole

Synonym(s): Sulfisomezole  |  sulfamethalazole  |  sulfamethazole

Class: Sulfa drug / Sulphonamide

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: 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 sufanilamide derivative; intermediate-acting (8-12 hours). Mostly used in fixed combination with trimethoprim (synergistic combination) for treatment and prophylaxis (oral and iv).
Year first mentioned: 1950
Development status: Approved, off-patent, discontinued in most countries as monotherapy
Chemical structure(s):
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Molecular weight: 253.28
Iso. SMILES: CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI Key: JLKIGFTWXXRPMT-UHFFFAOYSA-N
Can. SMILES: CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI: InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5329
Guide to Pharmacology: sulfamethoxazole
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8046889/

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