Differences in simulated liver concentrations of toxic coumarin metabolites in rats and different human populations evaluated through physiologically based biokinetic (PBBK) modeling

Toxicology in Vitro

Volumn 22, Issue 8, 2008, Pages 1890-1901

  Rietjens, Ivonne M C M ^a   Boersma, Marelle G ^a   Zaleska, Maria ^a   Punt, Ans ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Bioactivation; Coumarin; Interspecies differences; o Hydroxyphenylacetaldehyde (oHPA); Physiologically based biokinetic (PBBK) model

Indexed keywords

COUMARIN DERIVATIVE; CYTOCHROME P450 2A6;

ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; BODY WEIGHT; CATALYSIS; CHEMICAL REACTION KINETICS; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; HUMAN; HUMAN TISSUE; HYDROXYLATION; LIVER; LIVER MICROSOME; NONHUMAN; RAT; SIMULATION;

ACETALDEHYDE; ANIMALS; AREA UNDER CURVE; ARYL HYDROCARBON HYDROXYLASES; COUMARINS; HUMANS; HYDROXYLATION; MICROSOMES, LIVER; MODELS, BIOLOGICAL; RATS; SPECIES SPECIFICITY; TIME FACTORS; UMBELLIFERONES;

ANIMALIA; RATTUS;

EID: 55149120728     PISSN: 08872333     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tiv.2008.09.004     Document Type: Article

References (39)

1. Bergman, K. von, 1999. Sachverständigengutachten zur Beurteiling von Cumarin in Arzneimittel in Bezug auf lebertoxische wirkung beim Menschen, Dezember 21 1999 Bonn. Rheinische Freidich-Wilhelms-Universität Bonn, Deutschland. Available from the Federal Institute for Risk Assessment (BfR), Berlin, pp. 1-23.
2. Bogan D.P., Deasy B., O'Kennedy R., and Smyth M.R. Interspecies differences in coumarin metabolism in liver microsomes examined by capillary electrophoresis. Xenobiotica 26 (1996) 437-445
3. Born S.L., Rodriguez P.A., Eddy C.L., and Lehman-McKeeman L.D. Synthesis and reactivity of coumarin 3,4-epoxide. Drug Metabolism and Disposition. 25 (1997) 1318-1324
4. Born S.L., Hu J.K., and Lehman-McKeeman L.D. o-Hydroxyphenylacetaldehyde is a hepatotoxic metabolite of coumarin. Drug Metabolism and Disposition 28 (2000) 218-223
5. Born S.L., Caudill D., Smith B.J., and Lehman-McKeeman L.D. In vitro kinetics of coumarin 3,4-epoxidation: application to species differences in toxicity and carcinogenicity. Toxicological Sciences 58 (2000) 23-31
6. Born S.L., Caudill D., Fliter K.L., and Purdon M.P. Identification of the cytochromes P450 that catalyze coumarin 3,4-epoxidation and 3-hydroxylation. Drug Metabolism and Disposition 30 (2002) 483-487
7. Born S.L., Api A.M., Ford R.A., Lefever F.R., and Hawkins D.R. Comparative metabolism and kinetics of coumarin in mice and rats. Food and Chemical Toxicology 41 (2003) 247-258
8. Brown R.P., Delp M.D., Lindstedt S.L., Rhomberg L.R., and Beliles R.P. Physiological parameter values for physiologically based pharmacokinetic models. Toxicology and Industrial Health 13 (1997) 407-484
9. Burian M., Freudenstein J., Tegtmeier M., Naser-Hijazi B., Henneicke-von Zepelin H.-H., and Legrum W. Single copy of variant CYP2A6 alleles does not confer susceptibility to liver dysfunction in patients treated with coumarin. International Journal of Clinical Pharmacology and Therapeutics 41 (2003) 141-147
10. Carlton B.D., Aubrun J.-C., and Simon G.S. Effects of coumarin following perinatal and chronic exposure in Sprague-Dawley rats and CD-1 mice. Fundamental and Applied Toxicology 30 (1996) 145-151
11. Casalino E., Sblano C., Landriscina V., Calzaretti G., and Landriscina C. Rat liver glutathione S-transferase activity stimulation following acute cadmium or manganese intoxication. Toxicology 200 (2004) 29-38
12. DeJongh J., Verhaar H.J., and Hermens J.L. A quantitative property-property relationship (QPPR) approach to estimate in vitro tissue-blood partition coefficients of organic chemicals in rats and humans. Archives of Toxicology 72 (1997) 17-25
13. Draper A.J., Madan A., and Parkinson A. Inhibition of coumarin 7-hydroxylase activity in human liver microsomes. Archives of Biochemistry and Biophysics 341 (1997) 47-61
14. EFSA, 2004. Opinion of the scientific panel on food additives, flavourings, processing aids and materials in contact with food (AFC) on a request from the commission related to coumarin. Question Number EFSA-Q-2003-118. The EFSA Journal 104, 1-36.
15. Evans M.V., and Andersen M.E. Sensitivity analysis of a physiological model for 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD): assessing the impact of specific model parameters on sequestration in liver and fat in the rat. Toxicological Sciences 54 (2000) 71-80
16. Felter S.P., Vassallo J.D., Carlton B.D., and Daston G.P. A safety assessment of coumarin taking into account species-specificity of toxicokinetics. Food and Chemical Toxicology 44 (2006) 462-475
17. Fentem J.H., Fry J.R., and Whiting D.A. o-Hydroxyphenylacetaldehyde: a major novel metabolite of coumarin formed by rat, gerbil and human liver microsomes. Biochemical and Biophysical Research Communications 179 (1991) 197-203
18. Fernandez-Salguero P., Hoffman S.M.G., Cholerton S., Mohrenweiser H., Raunio H., Rautio A., Pelkonen O., Huang J.D., Evans W.E., Idle J.R., and Gonzalez F.J. A genetic polymorphism in coumarin 7-hydroxylation: sequence of the human CYP2A genes and identification of variant CYP2A6 alleles. American Journal of Human Genetics 57 (1995) 651-660
19. Garg A., and Balthasar J.P. Physiologically-based pharmacokinetic (PBPK) model to predict IgG tissue kinetics in wild-type and FcRn-knockout mice. Journal of Pharmacokinetics and Pharmacodynamics 34 (2007) 687-709
20. Hadidi H., Zahlsen K., Idel J.R., and Cholerton S. A single amino acid substitution (Leu160His) in cytochrome P450 CYP2A6 causes switching from 7-hydroxylation to 3-hydroxylation of coumarin. Food and Chemical Toxicology 35 (1997) 903-907
21. Hadidi H., Irshaid Y., Vågbø C.B., Brunsvik A., Cholerton S., Zahlsen K., and Idle J.R. Variability of coumarin 7- and 3-hydroxylation in a Jordanian population is suggestive of a functional polymorphism in cytochrome P450 of CYP2A6. European Journal of Clinical Pharmacology 54 (1998) 437-441
22. Hagan E.C. Food flavourings and compounds of related structure II. Subacute and chronic toxicity. Food Cosmetics Toxicology 12 (1967) 141-157
23. Lake B.G. Coumarin metabolism, toxicity and carcinogenicity: relevance for human risk assessment. Food and Chemical Toxicology 37 (1999) 423-453
24. Lake B.G., Gray T.J.B., Evans J.G., Lewis D.F.V., Beamand J.A., and Hue K.L. Studies on the mechanism of coumarin-induced toxicity in rat hepatocytes: comparison with dihydrocoumarin and other coumarin metabolites. Toxicology and Applied Pharmacology 97 (1989) 311-323
25. Lake B.G., Osborne D.J., Walters D.G., and Price R.J. Identification of o-hydroxyphenylacetaldehyde as a major metabolite of coumarin in rat hepatic microsomes. Food and Chemical Toxicology 30 (1992) 99-104
26. Loprinzi C.L., Kugler J.W., Sloan J.A., Rooke T.W., Quella S.K., Novotny P., Mowat R.B., Michalak J.C., Stella P.J., Levitt R., Tschetter L.K., and Windschitl H. Lack of effect of coumarin in women with lymphedema after treatment for breast cancer. New England Journal of Medicine 340 (1999) 346-350
27. Medinsky M.A., Leavens T.L., Csanády G.A., Gargas M.L., and Bond J.A. In vivo metabolism of butadiene by mice and rats: a comparison of physiological model predictions and experimental data. Carcinogenesis 7 (1994) 1329-1340
28. 1 mice (gavage studies). Technical Report No. NTP TR 422. NIH Publication No. 93-3153, US Department of Health and Human Services, NIH, Research Triangle Park, NC.
29. Planas-Bohne F., and Elizalde M. Activity of glutathione-S-transferase in rat liver and kidneys after administration of lead or cadmium. Archives of Toxicology 66 (1992) 365-367
30. Quick D.J., and Shuler M.L. Use of in vitro data for construction of a physiologically based pharmacokinetic model for naphthalene in rats and mice to probe species differences. Biotechnology Progress 15 (1999) 540-555
31. Ramsey J.C., and Andersen M.E. A physiologically based description of the inhalation pharmacokinetics of styrene in rats and humans. Toxicology and Applied Pharmacology 73 (1984) 159-175
32. SCF (Scientific Committee for Food), 1997. Opinion on coumarin (a constituent of natural flavouring source materials limited by annex II of flavourings directive 88/388/EC) expressed on 16 December 1994. Reports of the Scientific Committee for Food. Thirty-sixth series, pp. 13-20.
33. Schmeck-Lindenau H.J., Naser-Hijazi B., Becker E.W., Henneicke-von Zepelin H.H., and Schnitker J. Safety aspects of a coumarin-troxerutin combination regarding liver function in a double-blind placebo-controlled study. International Journal of Clinical Pharmacology and Therapeutics 41 (2003) 193-199
34. Steensma A., Beamand J.A., Walters D.G., Price R.J., and Lake B.G. Metabolism of coumarin and 7-ethoxycoumarin by rat, mouse, guinea pig, cynomolgus monkeys and human precision-cut liver slices. Xenobiotica 24 (1994) 893-907
35. Tardif R., Droz P.O., Charest-Tardif G., Pierrehumbert G., and Truchon G. Impact of human variability on the biological monitoring of exposure to toluene: I. Physiologically based toxicokinetic modelling. Toxicology Letters 134 (2002) 155-163
36. Van Iersel M., Walters D.G., Price R.J., Lovell D.P., and Lake B.G. Sex and strain differences in mouse hepatic coumarin 7-hydroxylase activity. Food and Chemical Toxicology 32 (1994) 387-390
37. Van Iersel M.L., Henderson C.J., Walters D.G., Price R.J., Wolf C.R., and Lake B.G. Metabolism of [3-14C] coumarin by human liver microsomes. Xenobiotoca 24 (1994) 795-803
38. Vanscheidt W., Rabe E., Naser-Hijazi B., Ramelet A.A., Partsch H., Diehm C., Schultz-Ehrenburg U., Spengel F., Wirsching M., Gotz V., Schnitker J., and Henneicke-von Zepelin H.H. The efficacy and safety of a coumarin-/troxerutin-combination (SB-LOT) in patients with chronic venous insufficiency: a double blind placebo-controlled randomised study. Vasa 31 (2002) 185-190
39. Vassallo J.D., Hicks S.M., Daston G.P., and Lehman-McKeeman L.D. Metabolic detoxification determines species differences in coumarin-induced hepatotoxicity. Toxicological Sciences 80 (2004) 249-257