Compound ID | 2058

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Sulfanilamide

Class: Sulfa drug / Sulphonamide

Spectrum of activity: Gram-positive
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 compound; active compound of prontosil; para-aminobenzoic acid (PABA) analogue. Topical use.
Year first mentioned: 1940
Development status: Discontinued
Chemical structure(s):
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Molecular weight: 172.21
Iso. SMILES: C1=CC(=CC=C1N)S(=O)(=O)N
InChI Key: FDDDEECHVMSUSB-UHFFFAOYSA-N
Can. SMILES: C1=C(C=CC(=C1)S(=O)(=O)N)N
InChI: InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5333
Guide to Pharmacology: sulfanilamide
Citations:
  • https://www.mdpi.com/2079-6382/9/8/456
  • https://www.nature.com/articles/nsb0697-490
  • https://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=&ved=2ahUKEwjJoKe46KH8AhWpsKQKHZB4BVA4RhAWegQIDhAB&url=https%3A%2F%2Fbrill.com%2Fdownloadpdf%2Fjournals%2Fges%2F45%2F1%2Farticle-p67_6.pdf&usg=AOvVaw140xK_dCoF3i7D_LhFz_UX

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