Compound ID | 2057

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Prontosil

Synonym(s): Sulfamidochrysoidine

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: Prodrug of sulfanilamide
Year first mentioned: 1935
Development status: Discontinued
Chemical structure(s):
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Molecular weight: 291.33
Iso. SMILES: C1=CC(=CC=C1N=NC2=C(C=C(C=C2)N)N)S(=O)(=O)N
InChI Key: ABBQGOCHXSPKHJ-UHFFFAOYSA-N
Can. SMILES: C1=C(C=C(C(=C1)N=NC2=CC=C(C=C2)S(=O)(=O)N)N)N
InChI: InChI=1S/C12H13N5O2S/c13-8-1-6-12(11(14)7-8)17-16-9-2-4-10(5-3-9)20(15,18)19/h1-7H,13-14H2,(H2,15,18,19)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/66895
Guide to Pharmacology: prontosil
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/3042521/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2601063/pdf/yjbm00510-0025.pdf

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