Full Characterization of Linezolid and Its Synthetic Precursors by Solid-State Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry

Journal of Pharmaceutical Sciences
Ewelina WielgusM J Potrzebowski

Abstract

In this work, for the first time we report complementary structural and spectral studies of linezolid and its synthetic precursors (R)-N-{3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl}methanol and (R)-N-{3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl}methyl azide employing solid-state nuclear magnetic resonance (SS NMR) spectroscopy and electron ionization mass spectrometry. Each technique provides unique and specific set of information. Through high-resolution SS NMR using (13) C, (15) N, and (19) F as structural probes, we revealed dynamic molecular disorder in the crystal lattice for polymorphs II and III of linezolid, never reported before. Utilizing variable temperature (13) C cross-polarization magic-angle spinning technique, we proved that the disorder has a local character. Only morpholine residue of linezolid is under fast regime exchange at room temperature. This process slows down at a lower temperature and stopped at 213 K. The mass spectrometry revealed that chemical modification at oxazolidinone end of linezolid has a significant influence on fragmentation pathways of studied drug and its synthetic precursors. In particular, the compound that has azide group at the methyl substituent in th...Continue Reading

References

Jan 11, 2003·Clinical Infectious Diseases : an Official Publication of the Infectious Diseases Society of America·Mary C BirminghamJerome J Schentag
Feb 15, 2003·Journal of Pharmaceutical Sciences·Patrick A TishmackStephen R Byrn
Apr 30, 2003·Rapid Communications in Mass Spectrometry : RCM·M Filomena DuarteM Lourdes Costa
Feb 24, 2006·The Analyst·Robin K Harris
Feb 3, 2007·The Journal of Pharmacy and Pharmacology·Robin K Harris
Nov 6, 2007·International Journal of Pharmaceutics·Elisabetta MaccaroniChiara Vladiskovic
Dec 25, 2007·Journal of Magnetic Resonance·Ulrich H N DürrAnne S Ulrich
Apr 19, 2008·Solid State Nuclear Magnetic Resonance·Th EmmlerG Buntkowsky
Aug 12, 2008·Current Clinical Pharmacology·Gabriele D'AndreaArgante Bozzi
Dec 2, 2009·Clinical Infectious Diseases : an Official Publication of the Infectious Diseases Society of America·G F SchecterS Mase
Jan 14, 2012·The Journal of Physical Chemistry. B·Tomasz PawlakMarek J Potrzebowski
Mar 17, 2012·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Martina UrbanovaLibor Kobera
Mar 13, 2014·The Journal of Physical Chemistry. B·Tomasz Pawlak, Marek J Potrzebowski
Aug 19, 2014·The Journal of Physical Chemistry. B·Frederick G VogtRoyston C B Copley

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Citations

Nov 1, 2017·Chemistry Central Journal·Katarzyna MichalskaJudyta Cielecka-Piontek
Oct 6, 2020·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Mehrnaz KhalajiMarek J Potrzebowski

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