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. 2020 Feb 24:14:715-730.
doi: 10.2147/DDDT.S239307. eCollection 2020.

Synthesis, Characterization, and Pharmacodynamics Study of Enrofloxacin Mesylate

Lin-Lin Pei #  1 , Wen-Zhu Yang #  1 , Jing-Yuan Fu #  1 , Meng-Xi Liu  1 , Ting-Ting Zhang  1 , Dong-Bo Li  1 , Ruo-Yue Huang  1 , Li Zhang  1 , Guang-Neng Peng  1 , Gang Shu  1 , Zhi-Xiang Yuan  2 , Ju-Chun Lin  1 , Wei Zhang  1 , Zhi-Jun Zhong  1 , Ling Zhao  1 , Hua-Lin Fu  1
Affiliations

Synthesis, Characterization, and Pharmacodynamics Study of Enrofloxacin Mesylate

Lin-Lin Pei et al. Drug Des Devel Ther. .

Abstract

Introduction: Enrofloxacin is used in the treatment of a wide variety of bacterial infections in mammals. However, its poor solubility limits the clinical use.

Methods: In order to improve the solubility of enrofloxacin, the enrofloxacin mesylate (EM) were obtained by a chemical synthesis method. The characterization of EM was carried out using ultraviolet scan (UV), synchronous thermal analysis (SDT), fourier transform infrared spectrometer (FTIR) and mass spectrometry (MS), nuclear magnetic resonance (NMR) and X-ray powder diffraction analysis (XRPD). Acute toxicity of EM in Kunming mice was studied. Besides, pharmacokinetic studies were performed in New Zealand rabbits at a single oral dose of 10 mg/kg, and the antibacterial activity of EM was also evaluated.

Results: EM was successfully synthesized and purified. The stoichiometric ratio of mesylate to enrofloxacin was 1:1 and the aqueous solubility of EM was 483.01±4.06 mg/mL, the solubility of EM was about 2000 times higher than enrofloxacin. The oral lethal dose (LD50) of EM was 1168.364 mg/kg, and the pharmacokinetics indicated that the oral relative bioavailability of EM was about 1.79 times and 1.48 times higher than that of enrofloxacin and enrofloxacin hydrochloride, respectively. In addition, the in vitro antibacterial activity of EM was not significantly changed compared with enrofloxacin and enrofloxacin hydrochloride.

Conclusion: EM has higher solubility, low toxicity for oral use, and increases the oral bioavailability in rabbit. This study may be of benefit for the development of new enrofloxacin drugs.

Keywords: acute toxicity; antibacterial effect; characterization; enrofloxacin mesylate; pharmacokinetics.

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Conflict of interest statement

The authors report no conflicts of interest in this work.

Figures

Figure 1
Figure 1
Chemical structure of enrofloxacin.
Figure 2
Figure 2
The UV spectrums of enrofloxacin and enrofloxacin mesylate.
Figure 3
Figure 3
The FTIR spectrums of enrofloxacin and enrofloxacin mesylate.
Figure 4
Figure 4
The FTIR spectrums of enrofloxacin hydrochloride and enrofloxacin mesylate.
Figure 5
Figure 5
The MS spectrum of enrofloxacin.
Figure 6
Figure 6
The MS spectrum of enrofloxacin mesylate.
Figure 7
Figure 7
The 1H-NMR spectrum of enrofloxacin.
Figure 8
Figure 8
The 1H-NMR spectrum of enrofloxacin mesylate.
Figure 9
Figure 9
The 13C-NMR spectrum of enrofloxacin.
Figure 10
Figure 10
The 13C-NMR spectrum of enrofloxacin mesylate.
Figure 11
Figure 11
The DSC-TGA analysis of enrofloxacin and enrofloxacin mesylate.
Figure 12
Figure 12
The X-ray powder diffraction analysis of enrofloxacin and enrofloxacin mesylate.
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