271
Views
13
CrossRef citations to date
0
Altmetric
Original Articles

Extrahepatic Metabolism by CYP2E1 in PBPK Modeling of Lipophilic Volatile Organic Chemicals: Impacts on Metabolic Parameter Estimation and Prediction of Dose Metrics

, &
Pages 1527-1541 | Received 01 Nov 2006, Accepted 24 Jan 2007, Published online: 17 Aug 2007

REFERENCES

  • Adams , E. M. , Spencer , H. C. , Rowe , V. K. , McCollister , D. and Irish , D. D. 1952 . Vapor toxicity of carbon tetrachloride determined by experiments on laboratory animals . AMA Arch. Ind. Hyg. Occup. Med. , 6 : 50 – 66 .
  • American Conference of Governmental Industrial Hygienists . 2004 . 2004 TLVs and BEIs: Based on the documentation of the threshold limit values for chemicla substances and physical agents & biological exposure indices , ACGIH .
  • Amet , Y. , Berthou , F. , Fournier , G. , Dreano , Y. , Bardou , L. , Cledes , J. and Menez , J. F. 1997 . Cytochrome P450 4A and 2E1 expression in human kidney microsomes . Biochem. Pharmacol. , 53 : 765 – 771 .
  • Anandatheerthavarada , H. K. , Shankar , S. K. , Bhamre , S. , Boyd , M. R. , Song , B. J. and Ravindranath , V. 1993 . Induction of brain cytochrome P-450IIE1 by chronic ethanol treatment . Brain Res. , 601 : 279 – 285 .
  • Andersen , M. E. 2003 . Toxicokinetic modeling and its applications in chemical risk assessment . Toxicol. Lett. , 138 : 9 – 27 .
  • Andersen , M. E. , Clewell , H. J. 3rd , Gargas , M. L. , Smith , F. A. and Reitz , R. H. 1987a . Physiologically based pharmacokinetics and the risk assessment process for methylene chloride . Toxicol. Appl. Pharmacol. , 87 : 185 – 205 .
  • Andersen , M. E. , Gargas , M. L. , Clewell , H. J. 3rd and Severyn , K. M. 1987b . Quantitative evaluation of the metabolic interactions between trichloroethylene and 1,1-dichloroethylene in vivo using gas uptake methods . Toxicol. Appl. Pharmacol. , 89 : 149 – 157 .
  • Andersen , M. E. , Meek , M. E. , Boorman , G. A. , Brusick , D. J. , Cohen , S. M. , Dragan , Y. P. , Frederick , C. B. , Goodman , J. I. , Hard , G. C. , O'Flaherty , E. J. and Robinson , D. E. 2000 . Lessons learned in applying the U.S. EPA proposed cancer guidelines to specific compounds . Toxicol. Sci. , 53 : 159 – 172 .
  • Andersen , N. J. , Waller , C. L. , Adamovic , J. B. , Thompson , D. J. , Allis , J. W. , Andersen , M. E. and Simmons , J. E. 1996 . A pharmacokinetic model of anaerobic in vitro carbon tetrachloride metabolism . Chem. Biol. Interact. , 101 : 13 – 31 .
  • Arms , A. D. and Travis , C. C. 1988 . Reference physiological parameters in pharmacokinetic modeling , Final Report : NTIS, EPA/600/688/004 .
  • ATSDR . 2005 . Toxicological profile for carbon tetrachloride , Atlanta, GA : Agency for Toxic Substances and Disease Registry, U.S. Department of Health and Human Services, Public Health Service .
  • Barton , H. A. and Clewell , H. J. 3rd. 2000 . Evaluating noncancer effects of trichloroethylene: Dosimetry, mode of action, and risk assessment . Environ. Health Perspect. , 108 ( suppl. 2 ) : 323 – 334 .
  • Barton , H. A. , Creech , J. R. , Godin , C. S. , Randall , G. M. and Seckel , C. S. 1995 . Chloroethylene mixtures: Pharmacokinetic modeling and in vitro metabolism of vinyl chloride, trichloroethylene, and trans-1,2-dichloroethylene in rat . Toxicol. Appl. Pharmacol. , 130 : 237 – 247 .
  • Barton , H. A. , Deisinger , P. J. , English , J. C. , Gearhart , J. N. , Faber , W. D. , Tyler , T. R. , Banton , M. I. , Teeguarden , J. and Andersen , M. E. 2000 . Family approach for estimating reference concentrations/doses for series of related organic chemicals . Toxicol. Sci. , 54 : 251 – 261 .
  • Brown , R. P. , Delp , M. D. , Lindstedt , S. L. , Rhomberg , L. R. and Beliles , R. P. 1997 . Physiological parameter values for physiologically based pharmacokinetic models . Toxicol. Ind. Health , 13 : 407 – 484 .
  • Bull , R. J. 2000 . Mode of action of liver tumor induction by trichloroethylene and its metabolites, trichloroacetate and dichloroacetate . Environ. Health Perspect. , 108 ( suppl. 2 ) : 241 – 259 .
  • Chiu , W. A. and White , P. 2006 . Steady-state solutions to PBPK models and their applications to risk assessment I: Route-to-route extrapolation of volatile chemicals . Risk Anal. , 26 : 769 – 780 .
  • Clark , L. H. , Setzer , R. W. and Barton , H. A. 2004 . Framework for evaluation of physiologically-based pharmacokinetic models for use in safety or risk assessment . Risk Anal. , 24 : 1697 – 1717 .
  • Clewell , H. J. 3rd , Andersen , M. E. and Barton , H. A. 2002 . A consistent approach for the application of pharmacokinetic modeling in cancer and noncancer risk assessment . Environ. Health Perspect. , 110 : 85 – 93 .
  • Clewell , H. J. 3rd , Gentry , P. R. , Covington , T. R. and Gearhart , J. M. 2000 . Development of a physiologically based pharmacokinetic model of trichloroethylene and its metabolites for use in risk assessment . Environ. Health Perspect. , 108 ( suppl. 2 ) : 283 – 305 .
  • Committee on Human Health Risks of Trichloroethylene, National Research Council . 2006 . Assessing the human health risks of tricholoroethylene: Key scientific issues , Washington, DC : The National Academies .
  • Constan , A. A. , Sprankle , C. S. , Peters , J. M. , Kedderis , G. L. , Everitt , J. I. , Wong , B. A. , Gonzalez , F. L. and Butterworth , B. E. 1999 . Metabolism of chloroform by cytochrome P450 2E1 is required for induction of toxicity in the liver, kidney, and nose of male mice . Toxicol. Appl. Pharmacol. , 160 : 120 – 126 .
  • Cummings , B. S. , Parker , J. C. and Lash , L. H. 2001 . Cytochrome p450-dependent metabolism of trichloroethylene in rat kidney . Toxicol. Sci. , 60 : 11 – 19 .
  • Delp , M. D. , Evans , M. V. and Duan , C. 1998 . Effects of aging on cardiac output, regional blood flow, and body composition in Fischer-344 rats . J. Appl. Physiol. , 85 : 1813 – 1822 .
  • Delp , M. D. , Manning , R. O. , Bruckner , J. V. and Armstrong , R. B. 1991 . Distribution of cardiac output during diurnal changes of activity in rats . Am. J. Physiol. , 261 : H1487 – H1493 .
  • DuTeaux , S. B. , Hengel , M. J. , DeGroot , D. E. , Jelks , K. A. and Miller , M. G. 2003 . Evidence for trichloroethylene bioactivation and adduct formation in the rat epididymis and efferent ducts . Biol. Reprod. , 69 : 771 – 779 .
  • el Ghissassi , F. , Barbin , A. and Bartsch , H. 1998 . Metabolic activation of vinyl chloride by rat liver microsomes: Low-dose kinetics and involvement of cytochrome P450 2E1 . Biochem. Pharmacol. , 55 : 1445 – 1452 .
  • Evans , M. V. , Crank , W. D. , Yang , H. M. and Simmons , J. E. 1994 . Applications of sensitivity analysis to a physiologically based pharmacokinetic model for carbon tetrachloride in rats . Toxicol. Appl. Pharmacol. , 128 : 36 – 44 .
  • Evelo , C. T. , Oostendorp , J. G. , ten Berge , W. F. and Borm , P. J. 1993 . Physiologically based toxicokinetic modeling of 1,3-butadiene lung metabolism in mice becomes more important at low doses . Environ. Health Perspect. , 101 : 496 – 502 .
  • Fedtke , N. , Boucheron , J. A. , Walker , V. E. and Swenberg , J. A. 1990 . Vinyl chloride-induced DNA adducts. II: Formation and persistence of 7-(2′-oxoethyl)guanine and N2,3-ethenoguanine in rat tissue DNA . Carcinogenesis , 11 : 1287 – 1292 .
  • Fisher , J. W. and Allen , B. C. 1993 . Evaluating the risk of liver cancer in humans exposed to trichloroethylene using physiological models . Risk Anal. , 13 : 87 – 95 .
  • Forkert , P. G. , Baldwin , R. M. , Millen , B. , Lash , L. H. , Putt , D. A. , Shultz , M. A. and Collins , K. S. 2005 . Pulmonary bioactivation of trichloroethylene to chloral hydrate: Relative contributions of CYP2E1, CYP2F, and CYP2B1 . Drug Metab. Dispos. , 33 : 1429 – 1437 .
  • Gargas , M. L. , Andersen , M. E. and Clewell , H. J. 3rd. 1986 . A physiologically based simulation approach for determining metabolic constants from gas uptake data . Toxicol. Appl. Pharmacol. , 86 : 341 – 352 .
  • Gargas , M. L. , Clewell , H. J. 3rd and Andersen , M. E. 1990 . Gas uptake inhalation techniques and the rates of metabolism of chloromethanes, chloroethanes, and chloroethylenes in the rat . Inhal. Toxicol. , 2 : 295 – 319 .
  • Guengerich , F. P. , Kim , D. H. and Iwasaki , M. 1991 . Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects . Chem. Res. Toxicol. , 4 : 168 – 179 .
  • Hissink , A. M. , Wormhoudt , L. W. , Sherratt , P. J. , Hayes , J. D. , Commandeur , J. N. , Vermeulen , N. P. and van Bladeren , P. J. 2000 . A physiologically-based pharmacokinetic (PB-PK) model for ethylene dibromide: Relevance of extrahepatic metabolism . Food Chem. Toxicol. , 38 : 707 – 716 .
  • Ivanetich , K. M. , Aronson , I. and Katz , I. D. 1977 . The interaction of vinyl chloride with rat hepatic microsomal cytochrome P-450 in vitro . Biochem. Biophys. Res. Commun. , 74 : 1411 – 1418 .
  • Jiang , Y. , Kuo , C. L. , Pernecky , S. J. and Piper , W. N. 1998 . The detection of cytochrome P450 2E1 and its catalytic activity in rat testis . Biochem. Biophys. Res. Commun. , 246 : 578 – 583 .
  • Keys , D. A. , Bruckner , J. V. , Muralidhara , S. and Fisher , J. W. 2003 . Tissue dosimetry expansion and cross-validation of rat and mouse physiologically based pharmacokinetic models for trichloroethylene . Toxicol. Sci. , 76 : 35 – 50 .
  • Kohn , M. C. 1997 . The importance of anatomical realism for validation of physiological models of disposition of inhaled toxicants . Toxicol. Appl. Pharmacol. , 147 : 448 – 458 .
  • Koop , D. R. 1986 . Hydroxylation of p-nitrophenol by rabbit ethanol-inducible cytochrome P-450 isozyme 3a . Mol. Pharmacol. , 29 : 399 – 404 .
  • Koop , D. R. 1992 . Oxidative and reductive metabolism by cytochrome P450 2E1 . FASEB J. , 6 : 724 – 730 .
  • Krishnan , K. and Johanson , G. 2005 . Physiologically-based pharmacokinetic and toxicokinetic models in cancer risk assessment . Environ. Sci. Health , 23 : 31 – 53 .
  • Lash , L. H. , Fisher , J. W. , Lipscomb , J. C. and Parker , J. C. 2000a . Metabolism of trichloroethylene . Environ. Health Perspect. , 108 ( suppl. 2 ) : 177 – 200 .
  • Lash , L. H. , Parker , J. C. and Scott , C. S. 2000b . Modes of action of trichloroethylene for kidney tumorigenesis . Environ. Health Perspect. , 108 ( suppl. 2 ) : 225 – 240 .
  • Lowry , O. H. , Rosebrough , N. J. , Farr , A. L. and Randall , R. J. 1951 . Protein measurement with the Folin phenol reagent . J. Biol. Chem. , 193 : 265 – 275 .
  • Maltoni , C. , Lefemine , G. , Ciliberti , A. , Cotti , G. and Carretti , D. 1981 . Carcinogenicity bioassays of vinyl chloride monomer: a model of risk assessment on an experimental basis . Environ. Health Perspect. , 41 : 3 – 29 .
  • Nakajima , T. , Wang , R. S. , Elovaara , E. , Park , S. S. , Gelboin , H. V. and Vainio , H. 1992 . A comparative study on the contribution of cytochrome P450 isozymes to metabolism of benzene, toluene and trichloroethylene in rat liver . Biochem. Pharmacol. , 43 : 251 – 257 .
  • Nakajima , T. , Wang , R. S. , Elovaara , E. , Park , S. S. , Gelboin , H. V. and Vainio , H. 1993 . Cytochrome P450-related differences between rats and mice in the metabolism of benzene, toluene and trichloroethylene in liver microsomes . Biochem. Pharmacol. , 45 : 1079 – 1085 .
  • Nestorov , I. A. , Aarons , L. J. , Arundel , P. A. and Rowland , M. 1998 . Lumping of whole-body physiologically based pharmacokinetic models . J. Pharmacokinet. Biopharm. , 26 : 21 – 46 .
  • Ramsey , J. C. and Andersen , M. E. 1984 . A physiologically based description of the inhalation pharmacokinetics of styrene in rats and humans . Toxicol. Appl. Pharmacol. , 73 : 159 – 175 .
  • Raucy , J. L. , Kraner , J. C. and Lasker , J. M. 1993 . Bioactivation of halogenated hydrocarbons by cytochrome P4502E1 . Crit. Rev. Toxicol. , 23 : 1 – 20 .
  • Reitz , R. H. , Gargas , M. L. , Andersen , M. E. , Provan , W. M. and Green , T. L. 1996 . Predicting cancer risk from vinyl chloride exposure with a physiologically based pharmacokinetic model . Toxicol. Appl. Pharmacol. , 137 : 253 – 267 .
  • Roberts , B. J. , Shoaf , S. E. , Jeong , K. S. and Song , B. J. 1994 . Induction of CYP2E1 in liver, kidney, brain and intestine during chronic ethanol administration and withdrawal: Evidence that CYP2E1 possesses a rapid phase half-life of 6 hours or less . Biochem. Biophys. Res. Commun. , 205 : 1064 – 1071 .
  • Sheets , P. L. , Yost , G. S. and Carlson , G. P. 2004 . Benzene metabolism in human lung cell lines BEAS-2B and A549 and cells overexpressing CYP2F1 . J. Biochem. Mol. Toxicol. , 18 : 92 – 99 .
  • Shimada , T. , Yamazaki , H. , Mimura , M. , Wakamiya , N. , Ueng , Y. F. , Guengerich , F. P. and Inui , Y. 1996 . Characterization of microsomal cytochrome P450 enzymes involved in the oxidation of xenobiotic chemicals in human fetal liver and adult lungs . Drug Metab. Dispos. , 24 : 515 – 522 .
  • Shimizu , M. , Lasker , J. M. , Tsutsumi , M. and Lieber , C. S. 1990 . Immunohistochemical localization of ethanol-inducible P450IIE1 in the rat alimentary tract . Gastroenterology , 99 : 1044 – 1053 .
  • Shultz , M. A. , Choudary , P. V. and Buckpitt , A. R. 1999 . Role of murine cytochrome P-450 2F2 in metabolic activation of naphthalene and metabolism of other xenobiotics . J. Pharmacol. Exp. Ther. , 290 : 281 – 288 .
  • Simmonds , A. C. , Reilly , C. A. , Baldwin , R. M. , Ghanayem , B. I. , Lanza , D. L. , Yost , G. S. , Collins , K. S. and Forkert , P. G. 2004 . Bioactivation of 1,1-dichloroethylene to its epoxide by CYP2E1 and CYP2F enzymes . Drug Metab. Dispos. , 32 : 1032 – 1039 .
  • Smith , A. E. and Evans , J. S. 1995 . Uncertainty in fitted estimates of apparent in vivo metabolic constants for chloroform . Fundam. Appl. Toxicol. , 25 : 29 – 44 .
  • Tjalve , H. and Lofberg , B. 1983 . Extrahepatic sites of metabolism of carbon tetrachloride in rats . Chem. Biol. Interact. , 46 : 299 – 316 .
  • U.S. Environmental Protection Agency . Integrated Risk Information System (IRIS) on methylene chloride . CASRN 75-09-2 . 1987 . Washington, DC: U.S. Environmental Protection Agency.
  • U.S. Environmental Protection Agency . 1992 . “ Carbon tetrachloride ” . In Integrated Risk Information System , Washington, DC : U.S. Environmental Protection Agency .
  • U.S. Environmental Protection Agency. 1996. 1996 National-Scale Air Toxics Assessment: Estimating ambient concentrations of air toxics across the contiguous United States. http://www.epa.gov/ttn/atw/nata
  • U.S. Environmental Protection Agency . 2000 . Toxicological review of vinyl chloride (CAS No. 75-01-4): In support of summary information on the integrated risk information system (IRIS) , Washington, DC : U.S. Environmental Protection Agency .
  • Vieira , I. , Pasanen , M. , Raunio , H. and Cresteil , T. 1998 . Expression of CYP2E1 in human lung and kidney during development and in full-term placenta: A differential methylation of the gene is involved in the regulation process . Pharmacol. Toxicol. , 83 : 183 – 187 .
  • Weber , L. W. , Boll , M. and Stampfl , A. 2003 . Hepatotoxicity and mechanism of action of haloalkanes: Carbon tetrachloride as a toxicological model . Crit. Rev. Toxicol. , 33 : 105 – 136 .
  • Woodruff , T. J. , Bois , F. Y. , Auslander , D. and Spear , R. C. 1992 . Structure and parameterization of pharmacokinetic models: Their impact on model predictions . Risk Anal. , 12 : 189 – 201 .
  • Zerilli , A. , Lucas , D. , Amet , Y. , Beauge , F. , Volant , A. , Floch , H. H. , Berthou , F. and Menez , J. F. 1995 . Cytochrome P-450 2E1 in rat liver, kidney and lung microsomes after chronic administration of ethanol either orally or by inhalation . Alcohol Alcohol. , 30 : 357 – 365 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.