Compound ID | 2075

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Sulfisoxazole

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; short-acting (4-8 hours). Oral and topical application.
Year first mentioned: 1949
Development status: Approved, off-patent, discontinued in most countries
Chemical structure(s):
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Molecular weight: 267.31
Iso. SMILES: CC1=C(ON=C1C)NS(=O)(=O)C2=CC=C(C=C2)N
InChI Key: NHUHCSRWZMLRLA-UHFFFAOYSA-N
Can. SMILES: CC1=C(NS(=O)(=O)C2=CC=C(C=C2)N)ON=C1C
InChI: InChI=1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5344
Guide to Pharmacology: sulfisoxazole
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/35820309/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8046889/
  • https://pubmed.ncbi.nlm.nih.gov/14795570/

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