S-3578, a new broad spectrum parenteral cephalosporin exhibiting potent activity against both methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa. Synthesis and structure-activity relationships

J Antibiot (Tokyo). 2002 Nov;55(11):975-92. doi: 10.7164/antibiotics.55.975.

Abstract

A series of 7-aminothiadiazolylcephalosporins having a 1-(substituted)-1H-imidazo[4,5-b]pyridinium group at the C-3' position of the cephem nucleus were synthesized and evaluated for in vitro antibacterial activities. Among the cephalosporins prepared in this study, 7beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetamido]-3-[1-(3-methylaminopropyl)-1H-imidazo[4,5-b]pyridinium-4-yl]methyl-3-cephem-4-carboxylate sulfate (S-3578) showed extremely potent broad spectrum activity against both gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA) and gram-negative bacteria including Pseudomonas aeruginosa, and good water solubility.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Cephalosporins / chemical synthesis*
  • Cephalosporins / chemistry
  • Cephalosporins / pharmacology*
  • Methicillin Resistance*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pseudomonas aeruginosa / drug effects*
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship

Substances

  • 7-(2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido)-3-(1-(3-methylaminopropyl)-1H-imidazo(4,5-b)pyridinium-4-yl)methyl-3-cephem-4-carboxylate
  • Anti-Bacterial Agents
  • Cephalosporins