AbstractIntroduction. The photostability is one of the most important properties of drugs. A comprehensive study of ofloxacin (OFX) and levofloxacin (LVX) photostability in aqueous solutions was performed. Ofloxacin is a chemotherapeutic agent belonging to the second generation fluoroquinolones and is a racemate of (R)-(+)-ofloxacin and (S)-(-)-ofloxacin (LVX).
Material and Methods. Samples of OFX and LVX were subjected to stress conditions of UV irradiation using a mercury-vapor lamp. The study involved development of enantioselective high-performance liquid chromatography (HPLC) and high-performance capillary electrophoresis (HPCE) methods for separation of OFX enantiomers and their degradation products. These methods were used to monitor the degradation process of OFX and LVX under irradiation and to determine the kinetics of degradation of these antibacterial agents. Moreover, the identification of photoproducts was also attempted. The structure of the main photoproducts was examined by mass spectrometry (MS).
Results and Conclusions. Using HPLC method it was possible to observe two products of OFX degradation and only one for LVX, while using HPCE method eight products of OFX degradation and six of LVX were observed. Some of the photoproducts retain character of optically active compounds. The trend of the photodegradation of both tested compounds was described by autocatalytic reaction proceeding according to the Prout-Tompkins model. Some of the products of the decomposition catalyze this reaction. The rate of degradation was similar for both enantiomers but t0.5 was slightly longer for LVX than OFX. Based on MS experiments the photodegradation products of the studied fluoroquinolones and possible pathways of UV induced decay were identified.
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- Andreu V, Blasco C, Picó Y. Analytical strategies to determine quinolone residues in food and the environment. TrAC Trends Anal Chem. 2007 Jun;26(6):534–556.
- Reid G, Potter P, Delaney G, Hsieh J, Nicosia S, Hayes K. Ofloxacin for the treatment of urinary tract infections and biofilms in spinal cord injury. Int J Antimicrob Agents. 2000 Feb;13(4):305–307.
- Cheng FC, Tsai TR, Chen YF, Hung LC, Tsai TH. Pharmacokinetic study of levofloxacin in rat blood and bile by microdialysis and high-performance liquid chromatography. J Chromatogr A. 2002 Jun;961(1):131–136.
- Hayakawa I, Atarashi S, Yokohama S, Imamura M, Sakano K, Furukawa M. Synthesis and antibacterial activities of optically active ofloxacin. Antimicrob Agents Chemother. 1986 Jan;29(1):163–164.
- Albini A, Fasani E (editors). Drugs, photochemistry and photostability. Cambridge (UK): Royal Society of Chemistry; 1998.
- Vasquez MI, Hapeshi E, Fatta-Kassinos D, Kümmerer K. Biodegradation potential of ofloxacin and its resulting transformation products during photolytic and photocatalytic treatment. Environ Sci Pollut Res Int. 2013 Mar;20(3):1302–1309.
- Gübitz G, Schmid MG (editors). Chiral Separations: Methods and Protocols. Totowa (NJ, USA): Humana Press; 2004.
- Stalcup AM. Chiral separations. Annu Rev Anal Chem (Palo Alto Calif). 2010;3:341–363.
- Horstkötter C, Blaschke G. Stereoselective determination of ofloxacin and its metabolites in human urine by capillary electrophoresis using laser-induced fluorescence detection. J Chromatogr B Biomed Sci Appl. 2001 Apr;754(1):169–178.
- Yamaguchi J, Oguchi H, Tokudome Y, Katsuyama M. A case of photosensitive drug eruption induced by sparfloxacin. Nishinihon J Dermatol. 1994;56:1146–1149.
- Yamaguchi J, Oguchi H, Tokudome Y, Katsuyama M. Three cases of photosensitive drug eruption induced by fleroxacin. Rinsho Hifuka. 1995;49:817–819.
- Christ W, Lehnert T. Toxicity of the quinolones. In: Siporin C, Heifetz CL, Domagala JM (editors). The New Generation of Quinolones. New York (USA): Marcel Dekker; 1990; p. 165–187.
- Cosa G. Photodegradation and photosensitization in pharmaceutical products: Assessing drug phototoxicity. Pure Appl Chem. 2004;76(2):263–275.
- Tokura Y. Quinolone photoallergy: photosensitivity dermatitis induced by systemic administration of photohaptenic drugs. J Dermatol Sci. 1998 Sep;18(1):1–10.
- Budai M, Gróf P, Zimmer A, Pápai K, Klebovich I, Ludányi K. UV light induced photodegradation of liposome encapsulated fluoroquinolones: An MS study. J Photochem Photobiol A. 2008 Aug;198(2–3):268–273.