In silico and in vitro genotoxicity evaluation of levofloxacin n-oxide, an impurity in levofloxacin

References

• Bercu JP, Dobo KL, Gocke E, McGovern TJ. 2009. Overview of genotoxic impurities in pharmaceutical development. Int J Toxicol 28:468–478.
   PubMed Web of Science ®Google Scholar
• Bolon MK. 2009. The newer fluoroquinolones. Infect Dis Clin North Am 23:1027–51, x.
   Google Scholar
• Clements J. 2000. The mouse lymphoma assay. Mutat Res 455:97–110.
   PubMed Web of Science ®Google Scholar
• Eichenbaum G, Johnson M, Kirkland D, O’Neill P, Stellar S, Bielawne J, DeWire R, Areia D, Bryant S, Weiner S, Desai-Krieger D, Guzzie-Peck P, Evans DC, Tonelli A. 2009. Assessment of the genotoxic and carcinogenic risks of p-nitrophenol when it is present as an impurity in a drug product. Regul Toxicol Pharmacol 55:33–42.
   PubMed Web of Science ®Google Scholar
• Ellison CM, Sherhod R, Cronin MT, Enoch SJ, Madden JC, Judson PN. 2011. Assessment of methods to define the applicability domain of structural alert models. J Chem Inf Model 51:975–985.
   PubMed Web of Science ®Google Scholar
• EMEA. 2006. Guideline on the limits of genotoxic impurities. London: EMEA.
   Google Scholar
• EMEA. 2009. Question & answers on the CHMP guideline on the limits of genotoxic impurities. London: EMEA.
   Google Scholar
• FDA. 2008. US FDA Draft guidance for Industry. Genotoxic and carcinogenic impurities in drug substances and products: recommended approaches. Silver Spring, MD: FDA.
   Google Scholar
• Hemeryck A, Mamidi RN, Bottacini M, Macpherson D, Kao M, Kelley MF. 2006. Pharmacokinetics, metabolism, excretion and plasma protein binding of 14C-levofloxacin after a single oral administration in the Rhesus monkey. Xenobiotica 36:597–613.
   PubMed Web of Science ®Google Scholar
• ICH. 2006a. Q3A(R2): Impurities in new drug substances. Geneva: ICH.
   Google Scholar
• ICH. 2006b. Q3B(R2): Impurities in new drug products. Geneva: ICH.
   Google Scholar
• Ishidate M Jr, Miura KF, Sofuni T. 1998. Chromosome aberration assays in genetic toxicology testing in vitro. Mutat Res 404:167–172.
   PubMed Web of Science ®Google Scholar
• Jacobson-Kram D, McGovern T. 2007. Toxicological overview of impurities in pharmaceutical products. Adv Drug Deliv Rev 59:38–42.
   PubMed Web of Science ®Google Scholar
• Macias AT, Mia MY, Xia G, Hayashi J, MacKerell AD Jr. 2005. Lead validation and SAR development via chemical similarity searching; application to compounds targeting the pY+3 site of the SH2 domain of p56lck. J Chem Inf Model 45:1759–1766.
   PubMed Web of Science ®Google Scholar
• Marchant CA, Briggs KA, Long A. 2008. In silico tools for sharing data and knowledge on toxicity and metabolism: derek for windows, meteor, and vitic. Toxicol Mech Methods 18 (2-3):177–187.
   PubMed Web of Science ®Google Scholar
• Matthews JM, Chen X, Cryan E, Hlasta DJ, Rybczynski PJ, Strauss K, Tang Y, Xu JZ, Yang M, Zhou L, Demarest KT. 2007. Design and synthesis of indane-ureido-thioisobutyric acids: A novel class of PPARalpha agonists. Bioorg Med Chem Lett 17:6773–6778.
   PubMed Web of Science ®Google Scholar
• Mayer J, Cheeseman MA, Twaroski ML. 2008. Structure-activity relationship analysis tools: validation and applicability in predicting carcinogens. Regul Toxicol Pharmacol 50:50–58.
   PubMed Web of Science ®Google Scholar
• Moore MM, Honma M, Clements J, Bolcsfoldi G, Burlinson B, Cifone M, Clarke J, Clay P, Doppalapudi R, Fellows M, Gollapudi B, Hou S, Jenkinson P, Muster W, Pant K, Kidd DA, Lorge E, Lloyd M, Myhr B, O’Donovan M, Riach C, Stankowski LF Jr, Thakur AK, Van Goethem F; Mouse Lymphoma Assay Workgroup, IWGT. 2007. Mouse lymphoma thymidine kinase gene mutation assay: meeting of the International Workshop on Genotoxicity Testing, San Francisco, 2005, recommendations for 24-h treatment. Mutat Res 627:36–40.
   PubMed Web of Science ®Google Scholar
• Moore MM, Honma M, Clements J, Bolcsfoldi G, Cifone M, Delongchamp R, Fellows M, Gollapudi B, Jenkinson P, Kirby P, Kirchner S, Muster W, Myhr B, O’Donovan M, Oliver J, Omori T, Ouldelhkim MC, Pant K, Preston R, Riach C, San R, Stankowski LF Jr, Thakur A, Wakuri S, Yoshimura I; Mouse Lymphoma Assay Workgroup. 2003. Mouse lymphoma thymidine kinase gene mutation assay: International Workshop on Genotoxicity Tests Workgroup report–Plymouth, UK 2002. Mutat Res 540:127–140.
   PubMed Web of Science ®Google Scholar
• Müller L, Mauthe RJ, Riley CM, Andino MM, Antonis DD, Beels C, DeGeorge J, De Knaep AG, Ellison D, Fagerland JA, Frank R, Fritschel B, Galloway S, Harpur E, Humfrey CD, Jacks AS, Jagota N, Mackinnon J, Mohan G, Ness DK, O’Donovan MR, Smith MD, Vudathala G, Yotti L. 2006. A rationale for determining, testing, and controlling specific impurities in pharmaceuticals that possess potential for genotoxicity. Regul Toxicol Pharmacol 44:198–211.
   PubMed Web of Science ®Google Scholar
• Shim SM, Choi MH, Kim GH. 2008. Safety evaluation of Elsholtzia splendens extracts: assessment of acute toxicity and mutagenicity. Food Chem Toxicol 46:1042–1047.
   PubMed Web of Science ®Google Scholar
• Soriano C, Creus A, Marcos R. 2007. Gene-mutation induction by arsenic compounds in the mouse lymphoma assay. Mutat Res 634 (1-2):40–50.
   Google Scholar
• Takayama S, Hirohashi M, Kato M, Shimada H. 1995. Toxicity of quinolone antimicrobial agents. J Toxicol Environ Health 45:1–45.
   PubMed Web of Science ®Google Scholar
• Venkatapathy R, Wang CY, Bruce RM, Moudgal C. 2009. Development of quantitative structure-activity relationship (QSAR) models to predict the carcinogenic potency of chemicals I. Alternative toxicity measures as an estimator of carcinogenic potency. Toxicol Appl Pharmacol 234:209–221.
   PubMed Web of Science ®Google Scholar
• Votano JR, Parham M, Hall LH, Kier LB, Oloff S, Tropsha A, Xie Q, Tong W. 2004. Three new consensus QSAR models for the prediction of Ames genotoxicity. Mutagenesis 19:365–377.
   PubMed Web of Science ®Google Scholar
• Witte BD, Langenhove HV, Hemelsoet K, Demeestere K, Wispelaere PD, Van Speybroeck V, Dewulf J. 2009. Levofloxacin ozonation in water: rate determining process parameters and reaction pathway elucidation. Chemosphere 76:683–689.
   PubMed Web of Science ®Google Scholar
• Yagawa K. 2001. Latest industry information on the safety profile of levofloxacin in Japan. Chemotherapy 47 Suppl 3:38–43; discussion 44–8.
   Google Scholar
• Yamada T, Odawara K, Kaneko H. 2000. Concurrent detection of gene mutations and chromosome aberrations induced by five chemicals in a CHL/IU cell line incorporating a gpt shuttle vector. Mutat Res 471 (1-2):29–36.
   Google Scholar