A chiral benzoquinolizine-2-carboxylic acid arginine salt active against vancomycin-resistant Staphylococcus aureus

J Med Chem. 2005 Aug 11;48(16):5232-42. doi: 10.1021/jm050035f.

Abstract

There is an urgent medical need for novel antibacterial agents to treat hospital infections, specially those caused by multidrug-resistant Gram-positive pathogens. The need may also be fulfilled by either exploring antibacterial agents having new mechanism of action or expanding known classes of antibacterial drugs. The paper describes a new chemical entity, compound 21, derived from hitherto little known "floxacin". The choice of the entity was made from a series of synthesized prodrugs and salts of the active chiral benzoquinolizine carboxylic acid, S-(-)-nadifloxacin. The chemistry, physicochemical characteristics, and essential bioprofile of 21 qualifies it for serious consideration as a novel drug entity against hospital infections of multi-drug-resistant Staphylococcus aureus, and its progress up to clinical phase I trials in humans is described.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Anti-Bacterial Agents / toxicity
  • Area Under Curve
  • Clinical Trials, Phase I as Topic
  • Dogs
  • Drug Resistance, Multiple, Bacterial
  • Female
  • Fluoroquinolones / chemical synthesis*
  • Fluoroquinolones / pharmacology
  • Fluoroquinolones / toxicity
  • Half-Life
  • Humans
  • Infusions, Intravenous
  • Injections, Intravenous
  • Male
  • Methicillin Resistance
  • Mice
  • Microbial Sensitivity Tests
  • Mutation
  • Prodrugs / chemical synthesis
  • Prodrugs / pharmacology
  • Prodrugs / toxicity
  • Quinolizines / chemical synthesis*
  • Quinolizines / pharmacology
  • Quinolizines / toxicity
  • Rats
  • Rats, Wistar
  • Staphylococcal Infections / drug therapy
  • Staphylococcus aureus / drug effects*
  • Staphylococcus aureus / genetics
  • Stereoisomerism
  • Structure-Activity Relationship
  • Vancomycin Resistance*

Substances

  • Anti-Bacterial Agents
  • Fluoroquinolones
  • Prodrugs
  • Quinolizines
  • nadifloxacin