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Permanganate oxidative products of moxifloxacin, a fluoroquinolone drug: a mechanistic approach

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Abstract

The kinetics of oxidation of moxifloxacin (MOX) was studied spectrophotometrically by a well-recognized analytical reagent, permanganate (Mn(VII), in aqueous alkaline medium at a constant ionic strength. The reaction was first order in [Mn(VII)] and less than unit order both in [MOX] and [alkali]. Retarding effect on rate of reaction was observed with an increase in ionic strength. The effect of dielectric constant of the medium was also studied. The multiple m/z values of ESI–MS spectra prove the existence of various oxidative products of MOX. The main product was identified as 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(octahydro-2-oxopyrrolo[3,4-b] pyridin-6-yl)-8-methoxy-4-oxoquinoline-3-carboxylic acid. The other three oxidative products from MOX in the present study are similar to the oxidative products of other fluoroquinolones oxidations. However, the abnormally high values of m/z could be assigned to the permanganate complexes of the products, which are unusual in the non-metallic oxidation of MOX. A composite mechanism involving the monohydropermangante as the reactive species of the oxidant has been proposed. Activation parameters and thermodynamic parameters are calculated and the reaction constants involved in the different steps of the mechanisms are calculated.

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Acknowledgments

The authors are grateful to the Principal, Karnatak Science College, Dharwad, Karnataka, India for providing the necessary facilities to carry out this work. They also thank the Raptakos Brett and Co., Microlabs Ltd. KLAB, Mumbai, India for providing the free sample of Moxifloxacin.

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  1. Department of Chemistry, Karnatak Science College, Dharwad, 580 001, Karnataka, India

    Seema S. Badi & Suresh M. Tuwar

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  1. Seema S. Badi
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Correspondence to Suresh M. Tuwar.

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Badi, S.S., Tuwar, S.M. Permanganate oxidative products of moxifloxacin, a fluoroquinolone drug: a mechanistic approach. Res Chem Intermed 41, 7827–7845 (2015). https://doi.org/10.1007/s11164-014-1862-8

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