A new rapid in vitro assay for assessing reactivity of acyl glucuronides

Drug Metabolism and Disposition

Volumn 43, Issue 11, 2015, Pages 1711-1717

  Zhong, Sheng ^a   Jones, Russell ^b   Lu, Wenzhe ^a   Schadt, Simone ^b   Ottaviani, Giorgio ^a  

^a Roche R and D Center China Ltd   (China)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL GLUCURONIDE; BENOXAPROFEN; CLOFIBRIC ACID; DABIGATRAN; DICLOFENAC; DIFLUNISAL; DRUG METABOLITE; FLUFENAMIC ACID; FUROSEMIDE; GEMFIBROZIL; GLUCURONIDE; IBUFENAC; IBUPROFEN; LEVOFLOXACIN; MECLOFENAMIC ACID; MONTELUKAST; NAPROXEN; PROBENECID; REPAGLINIDE; TELMISARTAN; TOLMETIN; UNCLASSIFIED DRUG; VALPROIC ACID; ZOMEPIRAC; CARBOXYLIC ACID;

ARTICLE; ASSAY; DRUG GLUCURONIDATION; DRUG HALF LIFE; HUMAN; INTERMETHOD COMPARISON; LIVER MICROSOME; MOLECULAR STABILITY; PRIORITY JOURNAL; ACYLATION; ANIMAL; BOVINE; DRUG EFFECTS; METABOLISM; PHYSIOLOGY; PROCEDURES; TANDEM MASS SPECTROMETRY; TIME FACTOR;

ACYLATION; ANIMALS; CARBOXYLIC ACIDS; CATTLE; GLUCURONIDES; HUMANS; MICROSOMES, LIVER; TANDEM MASS SPECTROMETRY; TIME FACTORS;

EID: 84946223180     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.115.066159     Document Type: Article

References (20)

1. Baba A and Yoshioka T (2009) Structure-activity relationships for the degradation reaction of 1-β-O-acyl glucuronides. Part 3: Electronic and steric descriptors predicting the reactivity of aralkyl carboxylic acid 1-β-O-acyl glucuronides. Chem Res Toxicol 22:1998-2008.
2. Bailey MJ and Dickinson RG (2003) Acyl glucuronide reactivity in perspective: biological consequences. Chem Biol Interact 145:117-137.
3. Benet LZ, Spahn-Langguth H, Iwakawa S., Volland C, Mizuma T, Mayer S., Mutschler E, and Lin ET (1993) Predictability of the covalent binding of acidic drugs in man. Life Sci 53: PL141-PL146.
4. Boelsterli UA (2002) Xenobiotic acyl glucuronides and acyl CoA thioesters as protein-reactive metabolites with the potential to cause idiosyncratic drug reactions. Curr Drug Metab 3: 439-450.
5. Bolze S, Bromet N, Gay-Feutry C, Massiere F., Boulieu R, and Hulot T (2002) Development of an in vitro screening model for the biosynthesis of acyl glucuronide metabolites and the assessment of their reactivity toward human serum albumin. Drug Metab Dispos 30:404-413.
6. Castillo M and Smith PC (1995) Disposition and reactivity of ibuprofen and ibufenac acyl glucuronides in vivo in the rhesus monkey and in vitro with human serum albumin. Drug Metab Dispos 23:566-572.
7. Chen Z, Holt TG, Pivnichny J.V., and Leung K (2007) A simple in vitro model to study the stability of acylglucuronides. J Pharmacol Toxicol Methods 55:91-95.
8. Di Meo F., Steel M, Nicolas P., Marquet P, Duroux JL, and Trouillas P (2013) Acylglucuronide in alkaline conditions: migration vs. hydrolysis. J Mol Model 19:2423-2432.
9. Ebner T, Heinzel G, Prox A., Beschke K, and Wachsmuth H (1999) Disposition and chemical stability of telmisartan 1-O-acylglucuronide. Drug Metab Dispos 27:1143-1149.
10. Ebner T, Wagner K, and Wienen W (2010) Dabigatran acylglucuronide, the major human metabolite of dabigatran: in vitro formation, stability, and pharmacological activity. Drug Metab Dispos 38:1567-1575.
11. Fenselau C (1994) Acyl glucuronides as chemically reactive intermediates, in Conjugation-Deconjugation Reactions in Drugs Metabolism and Toxicity (Kauffman FC ed) pp 367-389, Springer-Verlag, Berlin.
12. Food and Drug Administration (2008) Guidance for industry - Safety testing of drug metabolites.
13. Jinno N, Ohashi S, Tagashira M., Kohira T, and Yamada S (2013) A simple method to evaluate reactivity of acylglucuronides optimized for early stage drug discovery. Biol Pharm Bull 36: 1509-1513.
14. Jinno N, Tagashira M, Tsurui K., and Yamada S (2014) Contribution of cytochrome P450 and UDT-glucuronosyltransferase to the metabolism of drugs containing carboxylic acid groups: risk assessment of acylglucuronides using human hepatocytes. Xenobiotica 44:677-686.
15. Kaplowitz N (2013) Drug-induced liver injury: introduction and overview, in Drug-Induced Liver Disease, 3rd ed (Kaplowitz N and Deleve LD eds) pp 3-14, Elsevier, Amsterdam.
16. Sawamura R, Okudaira N, Watanabe K., Murai T, Kobayashi Y, Tachibana M., Ohnuki T, Masuda K, Honma H., and Kurihara A, et al. (2010) Predictability of idiosyncratic drug toxicity risk for carboxylic acid-containing drugs based on the chemical stability of acyl glucuronide. Drug Metab Dispos 38:1857-1864.
17. Schadt S, Chen LZ, and Bischoff D (2011) Evaluation of relative LC/MS response of metabolites to parent drug in LC/nanospray ionization mass spectrometry: potential implications in MIST assessment. J Mass Spectrom 46:1281-1286.
18. Walker GS, Atherton J, Bauman J., Kohl C, Lam W, Reily M., Lou Z, and Mutlib A (2007) Determination of degradation pathways and kinetics of acyl glucuronides by NMR spectroscopy. Chem Res Toxicol 20:876-886.
19. Wang J, Davis M, Li F., Azam F, Scatina J, and Talaat R (2004) A novel approach for predicting acyl glucuronide reactivity via Schiff base formation: development of rapidly formed peptide adducts for LC/MS/MS measurements. Chem Res Toxicol 17:1206-1216.
20. Williams AM and Dickinson RG (1994) Studies on the reactivity of acyl glucuronides-VI. Modulation of reversible and covalent interaction of diflunisal acyl glucuronide and its isomers with human plasma protein in vitro. Biochem Pharmacol 47:457-467.