AAPS PharmSciTech

, Volume 15, Issue 6, pp 1588–1597 | Cite as

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

  • Iqbal Ahmad
  • Raheela Bano
  • Syed Ghulam Musharraf
  • Sofia Ahmed
  • Muhammad Ali Sheraz
  • Qamar ul Arfeen
  • Muhammad Salman Bhatti
  • Zufi Shad
Research Article

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.

KEY WORDS

acid-base catalysis kinetics moxifloxacin photodegradation rate–pH profile solvent effect 

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Copyright information

© American Association of Pharmaceutical Scientists 2014

Authors and Affiliations

  • Iqbal Ahmad
    • 1
  • Raheela Bano
    • 1
  • Syed Ghulam Musharraf
    • 2
  • Sofia Ahmed
    • 1
  • Muhammad Ali Sheraz
    • 1
  • Qamar ul Arfeen
    • 2
  • Muhammad Salman Bhatti
    • 2
  • Zufi Shad
    • 1
  1. 1.Baqai Institute of Pharmaceutical SciencesBaqai Medical UniversityKarachiPakistan
  2. 2.H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological SciencesUniversity of KarachiKarachiPakistan

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