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Photodegradation of moxifloxacin in aqueous and organic solvents: a kinetic study.

Authors
Type
Published Article
Journal
AAPS PharmSciTech
1530-9932
Publisher
American Association of Pharmaceutical Scientists
Publication Date
Volume
15
Issue
6
Pages
1588–1597
Identifiers
DOI: 10.1208/s12249-014-0184-x
PMID: 25139764
Source
Medline
License
Unknown

Abstract

The kinetics of photodegradation of moxifloxacin (MF) in aqueous solution (pH 2.0-12.0), and organic solvents has been studied. MF photodegradation is a specific acid-base catalyzed reaction and follows first-order kinetics. The apparent first-order rate constants (kobs) for the photodegradation of MF range from 0.69 × 10(-4) (pH 7.5) to 19.50 × 10(-4) min(-1) (pH 12.0), and in organic solvents from 1.24 × 10(-4) (1-butanol) to 2.04 × 10(-4) min(-1) (acetonitrile). The second-order rate constant (k2) for the [H(+)]-catalyzed and [OH(-)]-catalyzed reactions are 6.61 × 10(-2) and 19.20 × 10(-2) M(-1) min(-1), respectively. This indicates that the specific base-catalyzed reaction is about three-fold faster than that of the specific acid-catalyzed reaction probably as a result of the rapid cleavage of diazabicyclononane side chain in the molecule. The kobs-pH profile for the degradation reactions is a V-shaped curve indicating specific acid-base catalysis. The minimum rate of photodegradation at pH 7-8 is due to the presence of zwitterionic species. There is a linear relation between kobs and the dielectric constant and an inverse relation between kobs and the viscosity of the solvent. Some photodegraded products of MF have been identified and pathways proposed for their formation in acid and alkaline solutions.

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