Characterization of clinafloxacin photodegradation products by LC-MS/MS and NMR.
Exposure of clinafloxacin to light results in photochemical degradation. The polar and nonpolar photodegradation products were profiled by HPLC using two sets of conditions. Clinafloxacin was subjected to severe light exposure conditions to obtain elevated levels of the photodegradation products for characterization. The structures of eight new degradation products were elucidated based on information from LC-MS/MS fragmentation and NMR spectra following isolation by preparative HPLC. Two photodegradation routes were identified: (1) dechlorination, followed by further reactions involving the quinolone ring, to yield polar photodegradation products; and (2) degradation of the pyrrolidine side-chain, yielding the nonpolar photodegradation products.
Analytical Development Department, Parke-Davis Pharmaceutical Research, Division of Warner-Lambert, Ann Arbor, MI 48105, USA.
M J
MJ
Lovdahl
S R
SR
Priebe
D000890:Anti-Infective Agents / Q000737:chemistry*; D002853:Chromatography, Liquid / Q000379:methods*; D024841:Fluoroquinolones; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D013058:Mass Spectrometry / Q000379:methods*; D010777:Photochemistry
D000890:Anti-Infective Agents; D024841:Fluoroquinolones; C057477:clinafloxacin