Characterization of benzimidazole and other oxidative and conjugative metabolites of brimonidine in vitro and in rats in vivo using on-line H/D exchange LC-MS/MS and stable-isotope tracer techniques

References

• Acheampong A, Chien D, Lam S, Cekich S, Breau A, Usansky J, Harcourt D, Munk S, Nguyen H, Garst M, et al. Characterization of brimonidine metabolism with rat, rabbit, dog, monkey and human liver fractions and rabbit liver aldehyde oxidase. Xenobiotica 1996; 26(10)1035–1055
   PubMed Web of Science ®Google Scholar
• Acheampong A, Shackleton M, Tang-Liu D. Comparative ocular pharmacokinetics of brimonidine after a single dose application to the eyes of albino and pigmented rabbits. Drug Metabolism and Disposition 1995; 23(7)708–712
   PubMed Web of Science ®Google Scholar
• Angelov O, Wiese A, Tang-Liu D, Acheampong A, Ismail I, Brar B. Preclinical safety profile of brimonidine. European Journal of Ophthalmology 1996; 6(1)21–25
   Google Scholar
• Baillie TA, Neill E, Hughes H, Davies DL, Davies DS. Application of stable isotope labeling in studies of the metabolism of clonidine in rat liver. International Conference In Proceeding of the 3rd International Conference on Stable Isotopes, New York: Academic, 1979, RE Klein, PD Klein. 415–425
   Google Scholar
• Bailie TA, Rettenmeier AW. Recent Advances in the use of stable isotopes in drug metabolism research. Journal of Clinical Pharmacology 1986; 26: 481–484
   Google Scholar
• Beedham C, Al-Tayib Y, Smith JA. Role of guinea pig and rabbit hepatic aldehyde oxidase in oxidative in vitro metabolism of cinchona antimalarials. Drug Metabolism and Disposition 1992; 20(6)889–95
   Google Scholar
• Damani LA, Crooks PA. Oxidative metabolism of heterocyclic rings. Metabolic basis of detoxification, WB Jakoby, JR Bend, J Caldwell. Academic, New York 1982; 69–90
   Google Scholar
• He M, Abraham TL, Lindsay TJ, Chay SH, Czeskis BA, Shipley LA. Metabolism and disposition of moxonidine in Fischer 344 rats. Drug Metabolism and Disposition 2000; 28(4)446–59
   Google Scholar
• He M, Abraham TL, Lindsay TJ, Schaefer HC, Pouliquen IJ, Payne C, Czeskis B, Shipley LA, Oliver SD, Mitchell MI. Metabolism and disposition of the antihypertensive agent moxonidine in humans. Drug Metabolism and Disposition 2003; 31(3)334–342
   Google Scholar
• Jeon YT, Gluchowski C. PCT US95/09895 (2003) and WO 96/04270 (1999)
   Google Scholar
• Johnson C, Stubley C, Stell J. Elevation of molybdenum hydroxylase levels in rabbit liver after ingestion of phthalazine or its hydroxylated metabolite. Biochemical Pharmacology 1984; 33: 3699–3705
   PubMed Web of Science ®Google Scholar
• Leung LY, Baillie TA. Studies on the biotransformation of ketamine. II—quantitative significance of the N-demethylation pathway in rats in vivo determined by a novel stable isotope technique. Biomedical and Environmental Mass Spectrometry 1989; 18(6)401–404
   Google Scholar
• Liu DQ, Hop CECA. Strategies for characterization of drug metabolites using liquid chromatography-tandem mass spectrometry in conjunction with chemical derivatization and on-line H/D exchange approaches. Journal of Pharmaceutical and Biomedical Analysis 2005; 37(1)1–18
   PubMed Web of Science ®Google Scholar
• Liu DQ, Hop CECA, Beconi MG, Mao A, Chiu SHL. Use of on-line hydrogen/deuterium exchange to facilitate metabolite identification. Rapid Communication of Mass Spectrometry 2001; 15: 1832–39
   PubMed Web of Science ®Google Scholar
• Ma S, Wwapan CK, Alton KB. Application of mass spectrometry for metabolite identification. Current Drug Metabolism 2006; 7: 503–523
   PubMed Web of Science ®Google Scholar
• Midgley I, Fowkes AG, Chasseaud LF, Hawkins DR, Girkin R. Biotransformation of lofexidine in humans. Xenobiotica 1983; 13(2)87–95
   PubMed Web of Science ®Google Scholar
• Ohashi N, Furuuchi S, Yoshikawa M. Retention mechanism of imidazoles in connective tissue. IV. Identification of a nucleophilic imidazolone metabolite in rats. Journal of Pharmaceutical and Biomedical Analysis 1998; 18: 325–34
   Google Scholar
• Schillings RT, Sisenwine S, Ruelius HW. Disposition and metabolism of lorazepam in the male rat. Drug Metabolism and Disposition 1977; 5(5)425–435
   Google Scholar
• Schulz-Jander DA, Casida JE. Imidacloprid insecticide metabolism: Human cyochrome P450 isozymes differ in selectivity for imidazolindine oxidation versus nitroimine reduction. Toxicology Letters 2002; 132: 65–70
   PubMed Web of Science ®Google Scholar
• Sisenwine SF, Tio CO. The metabolic disposition of oxazepam in rats. Drug Metabolism and Disposition 1986; 14(1)41–45
   Google Scholar
• Stubley C, Stell JGP, Mathieson DW. The oxidation of azaheterocycles with mammalian liver aldehyde oxidase. Xenobiotica 1979; 9: 475–484
   PubMed Web of Science ®Google Scholar
• Toris CB, Gleason ML, Camras CB, Yablonski ME. Effects of brimonidine on aqueous humor dynamics in human eyes. Archives of Ophthalmology 1995; 113: 1514–1517
   PubMed Web of Science ®Google Scholar
• Walters T. Development and use of brimonidine in treating acute and chronic elevations of intraocular pressure: A review of safety, efficacy, dose response and dosing studies. Survey of Ophthalmology 1996; 41: S19–26
   PubMed Web of Science ®Google Scholar