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Photodegradation profiling of nitrendipine: evaluation of active pharmaceutical ingredient, tablets and its altered forms

  • Special Issue: Original Paper
  • Frontiers of Separation Analysis
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Abstract

Nitrendipine (NTR) is a dihydropyridine drug, which is well-known as a photodegradable pharmaceutical. However, the photochemical reaction of NTR has not been evaluated in detail from now. In this study, we perform the photodegradation profiling of NTR for the elucidation of its photochemical behavior. NTR amounts during ultraviolet light (UV) irradiation were monitored using high performance liquid chromatography (HPLC). NTR was photodegraded almost completely within 24 h along with the generation of some photoproducts. Structural determination of two NTR photoproducts were carried out by means of electrospray ionization liquid chromatography tandem mass spectrometry (LC-ESI-MS/MS). Obtained results from this study clarified one novel NTR photoproduct, a nitroso pyridine analogue, in addition to a pyridine analogue. Furthermore, photodegradation pathway of NTR was speculated based on chemical structures of NTR photoproducts to clarify its photochemical behavior. It was proposed that a singlet oxygen molecule might withdraw two hydrogen radicals resulting in the form of a pyridine analogue, and the following reduction of its nitro group might produce a nitroso pyridine analogue. Finally, we evaluated the photostability of NTR tablets and its altered forms, indicating that the change of the dosage form led to a decrease of the photostability of NTR tablets. The obtained results will be helpful for the additional research to evaluate the effect of NTR photodegradation on its own biological activities.

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Data availability

The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Acknowledgements

The authors would like to thank Prof. Masaya Ikunaka for elucidating the photodegradation pathway. This work was supported by JSPS KAKENHI Grant No. 20K15980. A part of this work was supported by the Natural Science Center for Basic Research and Development (NBARD-00108), Hiroshima University.

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Author notes

  1. Kohei Kawabata and Haruka Muraoka contributed equally to this work.

Authors and Affiliations

  1. Faculty of Pharmacy, Yasuda Women’s University, 6-13-1 Yasuhigashi, Asaminami-ku, Hiroshima, 731-0153, Japan

    Kohei Kawabata, Haruka Muraoka & Hiroyuki Nishi

  2. Graduate School of Biomedical and Health Sciences, Hiroshima University, Kasumi 1-2-3, Minami-ku, Hiroshima, 734-8553, Japan

    Masatsugu Miyara & Yaichiro Kotake

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  1. Kohei Kawabata
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  2. Haruka Muraoka
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  5. Hiroyuki Nishi
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Correspondence to Kohei Kawabata.

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Kawabata, K., Muraoka, H., Miyara, M. et al. Photodegradation profiling of nitrendipine: evaluation of active pharmaceutical ingredient, tablets and its altered forms. ANAL. SCI. 39, 1791–1803 (2023). https://doi.org/10.1007/s44211-023-00400-x

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  • DOI: https://doi.org/10.1007/s44211-023-00400-x

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