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Xenobiotica
the fate of foreign compounds in biological systems
Volume 51, 2021 - Issue 1
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Molecular Toxicology

Evaluation of covalent binding of flutamide and its risk assessment using 19F-NMR

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Pages 88-94 | Received 30 Jul 2020, Accepted 26 Aug 2020, Published online: 22 Sep 2020

References

  • Anjum S, Swan SK, Lambrecht LJ, et al. (1999). Pharmacokinetics of flutamide in patients with renal insufficiency. Br J Clin Pharmacol 47:43–7.
  • Beasley CM, Jr, Tollefson GD, Tran PV. (1997). Safety of olanzapine. J Clin Psychiatry 58:13–7.
  • Brink A, Pähler A, Funk C, et al. (2017). Minimizing the risk of chemically reactive metabolite formation of new drug candidates: implications for preclinical drug design. Drug Discov Today 22:751–6.
  • Dahal UP, Obach RS, Gilbert AM. (2013). Benchmarking in vitro covalent binding burden as a tool to assess potential toxicity caused by nonspecific covalent binding of covalent drugs. Chem Res Toxicol 26:1739–45.
  • Degnan AP, Chaturvedula PV, Conway CM, et al. (2008). Discovery of (R)-4-(8-fluoro-2-oxo-1,2-dihydroquinazolin-3(4H)-yl)-N-(3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl)piperidine-1-carboxamide (BMS-694153): a potent antagonist of the human calcitonin gene-related peptide receptor for migraine with rapid and efficient intranasal exposure. J Med Chem 51:4858–61.
  • Di L, Kerns EH, Hong Y, et al. (2003). Optimization of a higher throughput microsomal stability screening assay for profiling drug discovery candidates. J Biomol Screen 8:453–62.
  • DiMasi JA, Grabowski HG, Hansen RW. (2016). Innovation in the pharmaceutical industry: new estimates of R&D costs. J Health Econ 47:20–33.
  • Evans DC, Watt AP, Nicoll-Griffith DA, et al. (2004). Drug–protein adducts: an industry perspective on minimizing the potential for drug bioactivation in drug discovery and development. Chem Res Toxicol 17:3–16.
  • Gan J, Harper TW, Hsueh M, et al. (2005). Dansyl glutathione as a trapping agent for the quantitative estimation and identification of reactive metabolites. Chem Res Toxicol 18:896–903.
  • Gandhi AS, Wohlfarth A, Zhu M, et al. (2015). High-resolution mass spectrometric metabolite profiling of a novel synthetic designer drug, N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide (STS-135), using cryopreserved human hepatocytes and assessment of metabolic stability with human liver microsomes. Drug Test Anal 7:187–98.
  • Gillis EP, Eastman KJ, Hill MD, et al. (2015). Applications of fluorine in medicinal chemistry. J Med Chem 58:8315–59.
  • Hu H, Katyayan KK, Czeskis BA, et al. (2017). Comparison between radioanalysis and 19F nuclear magnetic resonance spectroscopy in the determination of mass balance, metabolism, and distribution of pefloxacin. Drug Metab Dispos 45:399–408.
  • Isin EM, Elmore CS, Nilsson GN, et al. (2012). Use of radiolabeled compounds in drug metabolism and pharmacokinetic studies. Chem Res Toxicol 25:532–42.
  • James AD, Marvalin C, Luneau A, et al. (2017). Comparison of 19F NMR and 14C measurements for the assessment of ADME of BYL719 (alpelisib) in humans. Drug Metab Dispos 45:900–7.
  • Kakutani N, Nanayama T, Nomura Y. (2019). Novel risk assessment of reactive metabolites from discovery to clinical stage. J Toxicol Sci 44:201–11.
  • Kang P, Dalvie D, Smith E, et al. (2007). Identification of a novel glutathione conjugate of flutamide in incubations with human liver microsomes. Drug Metab Dispos 35:1081–8.
  • Lutz WK. (1979). In vivo covalent binding of organic chemicals to DNA as a quantitative indicator in the process of chemical carcinogenesis. Mutat Res 65:289–356.
  • Marathe PH, Shyu WC, Humphreys WG. (2004). The use of radiolabeled compounds for ADME studies in discovery and exploratory development. Curr Pharm Des 10:2991–3008.
  • Matsuzaki Y, Nagai D, Ichimura E, et al. (2006). Metabolism and hepatic toxicity of flutamide in cytochrome P450 1A2 knockout SV129 mice. J Gastroenterol 41:231–9.
  • Miyaji Y, Makino C, Kurihara A, et al. (2012). In vitro evaluation of the potential for drug-induced toxicity based on (35)S-labeled glutathione adduct formation and daily dose. Bioanalysis 4:263–9.
  • Mutlib A, Espina R, Atherton J, et al. (2012). Alternate strategies to obtain mass balance without the use of radiolabeled compounds: application of quantitative fluorine (19F) nuclear magnetic resonance (NMR) spectroscopy in metabolism studies. Chem Res Toxicol 25:572–83.
  • Nakayama S, Atsumi R, Takakusa H, et al. (2009). A zone classification system for risk assessment of idiosyncratic drug toxicity using daily dose and covalent binding. Drug Metab Dispos 37:1970–7.
  • Obach RS. (1999). Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: an examination of in vitro half-life approach and nonspecific binding to microsomes. Drug Metab Dispos 27:1350–9.
  • Pan Y. (2019). The dark side of fluorine. ACS Med Chem Lett 10:1016–9.
  • Park BK, Boobis A, Clarke S, et al. (2011). Managing the challenge of chemically reactive metabolites in drug development. Nat Rev Drug Discov 10:292–306.
  • Sakatis MZ, Reese MJ, Harrell AW, et al. (2012). Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds. Chem Res Toxicol 25:2067–82.
  • Schering-Plough Research Institute. (2020). Eulexin (flutamide) [package insert]. U.S. Food and Drug Administration. Available from: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/18554s23lbl.pdf [last accessed 17 Apr 2020].
  • Spraul M, Freund AS, Nast RE, et al. (2003). Advancing NMR sensitivity for LC-NMR-MS using a cryoflow probe: application to the analysis of acetaminophen metabolites in urine. Anal Chem 75:1536–41.
  • The Ministry of Health, Labour and Welfare. (2016). The  Japanese pharmacopoeia. 17th ed. Tokyo (Japan). http://www.mhlw.go.jp/file/06-Seisakujouhou-11120000-Iyakushokuhinkyoku/JP17_REV_1.pdf
  • Thompson RA, Isin E, Li Y, et al. (2012). In vitro approach to assess the potential for risk of idiosyncratic adverse reactions caused by candidate drugs. Chem Res Toxicol 25:1616–32.
  • Welte H, Zhou T, Mihajlenko X, et al. (2020). What does fluorine do to a protein? Thermodynamic, and highly-resolved structural insights into fluorine-labelled variants of the cold shock protein. Sci Rep 10:2640.
  • Xu HN, Liu Y, Zhang L. (2015). Salting-out and salting-in: competitive effects of salt on the aggregation behavior of soy protein particles and their emulsifying properties. Soft Matter 11:5926–32.
  • Zhang D, Luo G, Ding X, et al. (2012). Preclinical experimental models of drug metabolism and disposition in drug discovery and development. Acta Pharm Sin B 2:549–61.

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