AAPS PharmSciTech

, Volume 19, Issue 3, pp 1182–1190 | Cite as

Photodegradation of Moxifloxacin Hydrochloride Solutions under Visible Light Irradiation: Identification of Products and the Effect of pH on their Formation

  • Jie Zhou
  • Mingxian Li
  • Lan Luo
  • Hongbin Gao
  • Feng Zheng
Research Article
  • 72 Downloads

Abstract

The photodegradation study is essential for the phototoxicity assessment of fluoroquinolones. Various LC-MS techniques and ultraviolet (UV) lamp irradiation conditions have been used for the identification of their photodegradation products. In this study, visible light (400–760 nm) lamp irradiation was selected for the photodegradation of moxifloxacin (MOXI) hydrochloride solutions. Two photodegradation products were identified by LC-MS/MS at first, but one product could not be speculated from the mass spectrum and any known degradation mechanisms. To obtain an adequate amount for the structure elucidation, this unknown product was isolated by recrystallization and semi-preparative HPLC. Then, its structure was further identified by 1H–NMR, 13C–NMR, and 2D–NMR. Based on spectral data, this new photodegradation product was unambiguously named as 7-[3-(3-aminopropyl)-1H-pyrrol-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, which was formed through the open of hexahydroxy N-containing heterocycle and the formation of two alkene bonds in pyrrole ring. The effects of solution pH value on the formation of photodegradation products were compared. Their production was minimum at pH 5.0 and maximum at pH 7.0. Because MOXI hydrochloride has been used extensively in clinical practice and visible light is the most possible light source that pharmaceutical products are exposed to, our study is important for the quality control of MOXI liquid preparations.

Keywords

Moxifloxacin Visible light Photodegradation Identification 

Notes

Acknowledgements

This work was supported by the Priority Academic Program Development of Jiangsu Higher Education Institutions and the Open Project Program of MOE Key Laboratory of Drug Quality Control and Pharmacovigilance (No. DQCP2015MS04).

Compliance with Ethical Standards

Conflict of Interest

The authors declare that they have no conflicts of interest.

Supplementary material

12249_2017_929_MOESM1_ESM.docx (2.6 mb)
ESM 1 (DOCX 2675 kb)

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Copyright information

© American Association of Pharmaceutical Scientists 2017

Authors and Affiliations

  • Jie Zhou
    • 1
    • 2
  • Mingxian Li
    • 1
    • 2
  • Lan Luo
    • 1
    • 2
  • Hongbin Gao
    • 3
  • Feng Zheng
    • 1
    • 2
    • 4
  1. 1.Key Laboratory of Drug Quality Control and Pharmacovigilance, Ministry of EducationChina Pharmaceutical UniversityNanjingChina
  2. 2.Department of Pharmaceutical AnalysisChina Pharmaceutical UniversityNanjingChina
  3. 3.Department of Pharmacy, Changhai HospitalSecond Military Medical UniversityShanghaiChina
  4. 4.Key Laboratory on Protein Chemistry and Structural BiologyChina pharmaceutical UniversityNanjingChina

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