Abstract
Fluoroquinolones are a known antibacterial class commonly used around the world. These compounds present relative stability and they may show some adverse effects according their distinct chemical structures. The chemical hydrolysis of five fluoroquinolones was studied using alkaline and photolytic degradation aiming to observe the differences in molecular reactivity. DFT/B3LYP-6.31G* was used to assist with understanding the chemical structure degradation. Gemifloxacin underwent degradation in alkaline medium. Gemifloxacin and danofloxacin showed more degradation perceptual indices in comparison with ciprofloxacin, enrofloxacin and norfloxacin in photolytic conditions. Some structural features were observed which may influence degradation, such as the presence of five member rings attached to the quinolone ring and the electrostatic positive charges, showed in maps of potential electrostatic charges. These measurements may be used in the design of effective and more stable fluoroquinolones as well as the investigation of degradation products from stress stability assays.
Highlights
Quinolones are a group of synthetic broad spectrum antibacterial drugs commonly used throughout the world
Quinolones shows fast degradation under photolytic conditions, demonstrating high susceptibility to drug degradation when exposed to UV radiation, as described in the literature (Burhenne, Ludwig, Spiteller, 1999; Sunderland et al, 2001; Torniainen, Askolin, Mattinen 2007; Paim et al, 2010)
Alsante et al (2007) suggested a degradation of 5-20% for establishing a stability method, since intermediate degradation products should not interfere in drug analysis
Summary
Quinolones are a group of synthetic broad spectrum antibacterial drugs commonly used throughout the world. Nalidixic acid was the first compound introduced for therapeutics in 1962 for the treatment of urinary tract infections (Andersson, MacGowan, 2003; Petri, 2005). There are four generations of quinolones available for clinical use (Andersson, MacGowan, 2003; Petri, 2005), the main quinolones have a fluoro moiety attached to position 6. The stability of drugs is a critical point of quality control and pharmacology for therapeutic agents, since a non-stable or reactive molecule may influence its structure, efficacy and safety. Known as forced degradation studies, are important tools used to detect, quantify and identify the generation of degradation products (Alsante et al.; 2007; Singh et al, 2013).
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