The Fluoroquinolone Toxicity Research Foundation

 
  You are visitor number Counter
The Research Directory   


Misc 10
Quinolones differ in the number and placement of nitrogen in the 4-quinolone nucleus. These include the quinoline derivatives (ciprofloxacin, norfloxacin, ofloxacin, perfloxacin), cinnoline derivatives (cinoxacin), and naphthyridine derivatives (enoxacin, nalidixic acid). Quinolones that contain a fluorine atom are classified as fluoroquinolone. These include ciprofloxacin, enoxacin, grepafloxacin, levofloxacin, lomefloxacin, norfloxacin, ofloxacin, perfloxacin, sparfloxacin, and trovafloxacin. Fluoroquinolones have an expanded spectrum of acitivity and inreased antibacterial potency compared with nonfluorinated quinolones (cinoxacin, nalidixic acid, oxolinic acid).

These two drugs are both derivatives of quinoline, a heterocyclic aromatic structure consisting of two joined benzene rings with a nitrogen atom substituted for one carbon. The quinoline chemical structure provides many sites which, under certain reaction conditions, can be substituted with various functional groups. Chapter 11 in our textbook Organic Chemistry, deals with the topic of heterocyclic aromatic compounds of this type. Other chapters in the book regarding functional groups and methods of aromatic substitution etc. also would pertain to the synthesis of this drug. Most likely both compounds, from their starting materials, undergo reactions such as electrophilic aromatic substitution to introduce the fluorine component onto the compound. (http://www.chem.qmw.ac.uk/iupac/fusedring/FR22.html) Many other processes to introduce functional groups such as the carboxylic acid can be found in the textbook. Chapters 19 and 20 apply to the carboxylic acid group.