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Photodegradation of Moxifloxacin in Aqueous and Organic Solvents: A Kinetic Study

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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 (k obs) 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 (k 2) 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 k obs-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 k obs and the dielectric constant and an inverse relation between k obs 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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Authors and Affiliations

  1. Baqai Institute of Pharmaceutical Sciences, Baqai Medical University, Toll Plaza, Super highway, Gadap Road, Karachi, 74600, Pakistan

    Iqbal Ahmad, Raheela Bano, Sofia Ahmed, Muhammad Ali Sheraz & Zufi Shad

  2. H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

    Syed Ghulam Musharraf, Qamar ul Arfeen & Muhammad Salman Bhatti

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  1. Iqbal Ahmad
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Correspondence to Muhammad Ali Sheraz.

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Ahmad, I., Bano, R., Musharraf, S.G. et al. Photodegradation of Moxifloxacin in Aqueous and Organic Solvents: A Kinetic Study. AAPS PharmSciTech 15, 1588–1597 (2014). https://doi.org/10.1208/s12249-014-0184-x

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