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Original Articles

In Vitro Metabolism of the Fungicide and Environmental Contaminant trans-bromuconazole and Implications for Risk Assessment

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Pages 1241-1250 | Received 06 Oct 2006, Accepted 24 Nov 2006, Published online: 15 Jun 2007

REFERENCES

  • Ankley , G. T. , Jensen , K. M. , Durhan , E. J. , Makynen , E. A. , Butterworth , B. C. , Kahl , M. D. , Villeneuve , D. L. , Linnum , A. , Gray , L. E. , Cardon , M. and Wilson , V. S. 2005 . Effects of two fungicides with multiple modes of action on reproductive endocrine function in the fathead minnow (Pimephales promelas) . Toxicol. Sci , 86 : 300 – 308 .
  • Austin , R. P. , Barton , P. , Cockroft , S. L. , Wenlock , M. C. and Riley , R. J. 2002 . The influence of nonspecific microsomal binding on apparent intrinsic clearance, and its prediction from physicochemical properties . Drug Metab. Dispos , 30 : 1497 – 1503 .
  • Barton , H. A. , Tang , J. , Sey , Y. M. , Stanko , J. P. , Murrell , R. N. , Rockett , J. C. and Dix , D. J. 2006 . Metabolism of myclobutanil and triamefon by human and rat cytochrome P450 enzymes and liver microsomes . Xenobiotica , 36 : 793 – 806 .
  • Bradford , M. M. 1976 . A rapid and sensitive method for the quantification of microgram quantities of protein utilizing protein-dye binding . Anal. Chem , 72 : 248 – 254 .
  • Campbell , G. F. , Crous , P. W. and Lucas , J. A. 1999 . Pyrenophora teres f. maculata, the cause of Pyrenophora leaf spot of barley in South Africa . Mycol. Res , 103 : 257 – 267 .
  • Carlile , D. J. , Zomorodi , K. and Houston , J. B. 1997 . Scaling factors to relate drug metabolic clearance in hepatic microsomes, isolated hepatocytes, and the intact liver: studies with induced livers involving diazepam . Drug Metab. Dispos , 25 : 903 – 911 .
  • Cook , C. S. , Karim , A. and Sollman , P. 1982 . Stereoselectivity in the metabolism of disopyramide enantiomers in rat and dog . Drug Metab. Dispos , 10 : 116 – 121 .
  • Dennison , J. E. , Bigelow , P. L. and Andersen , M. E. 2004 . Occupational exposure limits in the context of solvent mixtures, consumption of ethanol, and target tissue dose . Toxicol. Ind Health , 20 : 165 – 175 .
  • Department for Environment, F. A. R. A., Pesticide Safety Directorate. 1996 .Food and Environment Protection Act, 1985, Part III Issue 160. Control of Pesticide Regulations 1986
  • Dobrev , I. D. , Andersen , M. E. and Yang , R. S. 2001 . Assessing interaction thresholds for trichloroethylene in combination with tetrachloroethylene and 1,1,1-trichloroethane using gas uptake studies and PBPK modeling . Arch Toxicol. , 75 : 134 – 144 .
  • Estabrook , R. , Teterson , W. J. , Baron , J. and Hildebrandt , A. G. 1972 . The spectrophotometric measurment of turbid suspensions of cytochromes associated with drug metabolism . Meth. Pharmacol. , 2 : 303 – 350 .
  • Figueras-Roca , M. , Cristani , C. and Vannacci , G. 1996 . Sensitivity of Trichoderma isolates and selected resistant mutants to DMI fungicides . Crop Protect. , 15 : 615 – 620 .
  • Hegelund , T. , Ottosson , K. , Radinger , M. , Tomberg , P. and Celander , M. C. 2004 . Effects of the antifungal imidazole ketoconazole on CYPIA and CYP3A in rainbow trout and killifish . Environ. Toxicol. Chem. , 23 : 1326 – 1334 .
  • International Commission on Radiologic Protection . 1975 . Report of the Task Group on Reference Man , ICRP Publication 23. Oxford, UK : Pergamon Press .
  • Ito , K. and Houston , J. B. 2004 . Comparison of the use of liver models for predicting drug clearance using in vitro kinetic data from hepatic microsomes and isolated hepatocytes . Pharm. Res. , 21 : 785 – 792 .
  • Jarman , J. L. , Jones , W. J. J. , Howell , L. A. and Garrison , A. W. 2005 . Application of capillary electrophoresis to study the enantioselective transformation of five chiral pesticides in aerobic soil slurries . J. Agric. Food Chem. , 53 : 6175 – 6182 .
  • Lin , J. H. and Lu , A. Y. H. 1997 . Role of pharmacokinetics and metabolism in drug discovery and development . Pharmacol. Rev. , 49 : 403 – 449 .
  • Lipscomb , J. C. 2004 . Evaluating the relationship between variance in enzyme expression and toxicant concentration in health risk assessment . Hum. Ecol Risk Assess. , 10 : 39 – 55 .
  • Lipscomb , J. C. , Teuschler , L. K. , Swartout , J. , Popken , D. , Cox , T. and Kedderis , G. L. 2003 . The impact of cytochrome P450 2E1-dependent metabolic variance on a risk-relevant pharmacokinetic outcome in humans . Risk Anal. , 23 : 1221 – 1238 .
  • Liu , K. H. , Kim , M. J. , Shon , J. H. , Moon , Y. S. , Seol , S. Y. , Kang , W. , Cha , I. J. and Shin , J. G. 2005 . Stereoselective inhibition of cytochrome P450 forms by lansoprazole and omeprazole in vitro . Xenobiotica , 35 : 27 – 38 .
  • Lu , A. Y. H. , Wang , R. W. and Lin , J. H. 2003 . Cytochrome P450 in vitro reaction phenotyping: A re-evaluation of approaches used for P450 isoform identification . Drug Metab. Dispos. , 31 : 345 – 350 .
  • Monostory , K. , Hazai , E. and Cereczkey , L. 2004 . Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP 2E1 inhibitors . Chem. Biol. Interact. , 147 : 331 – 340 .
  • Nelson , D. R. , Zeldin , D. C. , Hoffman , S. M. , Maltais , L. J. , Wain , H. M. and Nebert , D. W. 2004 . Comparison of cytochrome P450 (CYP) genes from the mouse and human genomes, including nomenclature recommendations for genes, pseudogenes and alternative-splice variants . Pharmacogenetics , 14 : 1 – 18 .
  • Obach , R. S. 1997 . Nonspecific binding to microsomes: Impact on scale-up of in vitro intrinsic clearance to hepatic clearance as assessed through examination of warfarin, imipramine, and propranolol . Drug Metab. Dispos. , 25 : 1359 – 1369 .
  • Obach , R. S. , Baxter , J. G. , Liston , T. E. , Silber , B. M. , Jones , B. C. , MacIntyre , F. , Rance , D. J. and Wastall , P. 1997 . The prediction of human pharmacokinetic parameters from preclinical and in vitro metabolism data . J. Pharmacol. Exp. Ther. , 283 : 46 – 58 .
  • Riley , R. J. , Parker , A. J. , Trigg , S. and Manners , C. N. 2001 . Development of a generalized, quantitative physicochemical model of CYP3A4 inhibition for use in early drug discovery . Pharm. Res. , 18 : 652 – 655 .
  • Robbertse , B. , van der Rijst , M. , van Aarde , I. M. R. , Lennox , C. and Crous , P. W. 2001 . DMI sensitivity and cross-resistance patterns of Rhynchosporium secalis isolates from South Africa . Crop Protection , 20 : 97 – 102 .
  • Roberts , T. and Hutson , D. 1998 . Metabolic pathways of agrochemicals , Insecticides and Fungicides Part Two. The Royal Society of Chemistry 1999 .
  • Rogiers , V. , Adriaenssens , L. , Vandenberghe , Y. , Gepts , E. , Callaerts , A. and Vercruysse , A. 1986 . Critical evaluation of 7-ethoxycoumarin O-deethylase activity measurment in intact isolated rat hepatocytes . Xenobiotica , 16 : 817 – 826 .
  • Ronis , M. J. J. , Ingelman-Sundberg , M. and Badger , T. M. 1994 . Induction, suppression and inhibition of multiple hepatic cytochrome P450 isozymes in the male rat and bobwhite quail (Colinus virginianus) by ergosterol biosynthesis inhibiting fungicides (EBIFs) . Biochem. Pharmacol. , 48 : 1953 – 1965 .
  • Sato , T. 1987 . New method for measurement of hepatic blood flow in the rat using thermodilution method . Circ. Shock , 21 : 31 – 37 .
  • Snawder , J. E. and Lipscomb , J. C. 2000 . Interindividual variance of cytochrome P450 forms in human hepatic microsomes: Correlation of individual forms with xenobiotic metabolism and implications in risk assessment . Regul. Toxicol. Pharmacol. , 32 : 200 – 209 .
  • Sun , G. , Thai , S. F. , Tully , D. B. , Lambert , G. R. , Goetz , A. K. , Wolf , D. C. , Dix , D. J. and Nesnow , S. 2005 . Propiconazole-induced cytochrome P450 gene expression and enzymatic activities in rat and mouse liver . Toxicol. Lett. , 155 : 277 – 287 .
  • Tanacs , L. , Szabo , G. , Csatlos , I. and Matuz , J. 1997 . Study of fungicide residues in the grain of fungicide-treated wheats—II. Propiconazole- and bromuconazole-based fungicides . Cereal Res. Commun. , 25 : 1001 – 1006 .
  • Tassaneeyakul , W. , Birkett , D. J. and Miners , J. O. 1998 . Inhibition of human hepatic cytochrome P4502E1 by azole antifungals, CNS-active drugs and non-steroidal anti-inflammatory agents . Xenobiotica , 28 : 293 – 301 .
  • Timchalk , C. , Nolan , R. J. , Mendrala , A. L. , Dittenber , D. A. , Brzak , K. A. and Mattsson , J. L. 2002 . A physiologically based pharmacokinetic and pharmacodynamic (PBPK/PD) model for the organophosphate insecticide chlorpyrifos in rats and humans . Toxicol. Sci. , 66 : 34 – 53 .
  • Tocco , D. J. , Deluna , F. A. , Duncan , A. E. W. , Hsieh , J. H. and Lin , J. H. 1990 . Interspecies differences in stereoselective protein binding and clearance of MK-571 . Drug Metab. Dispos. , 18 : 388 – 392 .
  • Tredger , J. M. and Stoll , S. 2002 . Cytochromes P450, their impact on drug treament . Hosp. Pharm. , 9 : 167 – 173 .
  • Turan , V. K. , Mishin , V. M. and Thomas , P. E. 2001 . Clotrimazole is a selective and potent inhibitor of rat cytochrome P450 3A subfamily-related testosterone metabolism . Drug Metab. Dispos. , 29 : 837 – 842 .
  • U.S. Environmental Protection Agency. 2002. Determination of the appropriate FQPA safety factor(s) in tolerance assessment. Washington, DC: Office of Pesticide Programs, U.S. Environmental Protection Agency, February 28 http://www.epa.gov/pesticides/trac/science/determ.pdf
  • U.S. Environmental Protection Agency. 2004. Potential implications of genomics for regulatory and risk assessment applications at EPA. Washington, DC: Science Policy Council, U.S. Environmental Protection Agency. EPA 100/B-04/002, December http://www.epa.gov/osa/genomics.htm
  • U.S. Environmental Protection Agency . 2006 . Propiconazole risk assessments; Notice of availablity and risk reduction options . Fed. Reg. , 71 : 7949 – 7951 .
  • Venkatakrishnan , K. , von Moltke , L. L. and Greenblatt , D. J. 2000 . Effects of the anitfungal agents on oxidative drug metabolism . Clin. Pharmacokinet. , 38 : 111 – 180 .
  • Zarn , J. A. , Bruschweiler , B. J. and Schlatter , J. R. 2003 . Effects of azole fungicides on mammalian steroidogenesis by inhibiting sterol 14 alpha-demethylase and aromatase . Environ. Health Perspect. , 111 : 255 – 261 .

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