Human metabolism and metabolic interactions of deployment-related chemicals

Drug Metabolism Reviews

Volumn 37, Issue 1, 2005, Pages 1-39

  Hodgson, Ernest ^a   Rose, Randy L ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

Alcohol dehydrogenase; Aldehyde dehydrogenase; Carbamates; Chemical warfare agents; Cytochrome P450; Deployment related chemicals; Jet fuel components; Metabolic interactions; Metabolism; Organophosphorus compounds; Pyrethroids; Repellents

Indexed keywords

2 BUTOXYETHANOL; ACETIC ACID; ALCOHOL; BUTANOL; CARBARIL; CHEMICAL AGENT; CHLORPYRIFOS; CRESOL; CYCLOHEXANOL; CYTOCHROME P450; CYTOCHROME P450 2B6; CYTOCHROME P450 2C19; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; DIETHYLENE GLYCOL; DIETHYLTOLUAMIDE; ENZYME VARIANT; FUEL; HEXANOL; ISOENZYME; METHANOL; MUSTARD GAS; ORGANOPHOSPHATE INSECTICIDE; PERMETHRIN; PYRIDOSTIGMINE; RECOMBINANT ENZYME; SOLVENT; STEROID HORMONE; UNINDEXED DRUG; XENOBIOTIC AGENT;

CHEMICAL INTERACTION; CYTOSOL; ENZYME POLYMORPHISM; HIGH RISK POPULATION; HORMONE METABOLISM; HUMAN; HUMAN CELL; LIVER CELL; METABOLIC INHIBITION; METABOLISM; METABOLITE; MICROSOME; MOUSE; NONHUMAN; RAT; REVIEW; TECHNIQUE;

EID: 13844294107     PISSN: 03602532     EISSN: None     Source Type: Journal    
DOI: 10.1081/DMR-200046955     Document Type: Review

References (146)

1. Abou-Donia, M. B., Wilmarth, K. R., AbdelRahman, A. A., Jensen, K. F., Oehme, F. W., Kurt, T. L. (1996). Increased neurotoxicity following concurrent exposure to pyridostigmine bromide, DEET, and chlorpyrifos. Fundam. Appl. Toxicol. 34:201-222.
2. Adas, F., Berthou, F., Picard, D., Lozac'h, P., Beauge, F., Amet, Y. (1998). Involvement of cytochrome P450 in the (omega-1)-hydroxylation of oleic acid in human and hat liver microsomes. J. Lipid Res. 36:1210-1219.
3. Allen, D. G., Riviere, J. E., Monteiro-Riviere, N. A. (2000). Identification of early biomarkers of inflammation produced by keratinocytes exposed to jet fuels Jet A, JP-8 and JP8(100). J. Biochem. Mol. Toxicol. 14:231-237.
4. Allen, D. G., Riviere, J. E., Monteiro-Riviere, N. A. (2001). Cytokine induction as a measure of cutaneous toxicity in primary and immortalized porcine keratinocytes exposed to jet fuels, and their relationship to normal human epidermal keratinocytes. Toxicol. Lett. 119:209-217.
5. Angerer, J., Ritter, A. (1997). Determination of metabolites of pyrethroids in human urine using solid phase extraction and gas chromatography-mass spectrometry. J. Chromatogr. 695:217.
6. Asakawa, F., Jitsunari, F., Miki, K., Choi, J., Takeda, N., Kitamado, T., Suna, S., Manabe, Y. (1996). Agricultural worker exposure to and absorption of permethrin applied to cabbage. Bull. Environ. Toxicol. 56:42.
7. Assaf, P., Katzhendler, J., Haj-Yehia, A. I. (2000). 2-(4-Carboxyphenyl) -6-N,N-diethylaminobenzofuran: a useful reagent for the sensitive determination of alcohols by high-performance liquid chromatography with fluorimetric detection. J. Chromatogr., A 869:243-250.
8. ATSDR. (1995). Toxicological Profile for Naphthalene (Update), ed. Comparative Biochemistry and Metabolism: Part 2. Naphthalene Lung Toxicity. Boca Raton, FL: Agency for Toxic Substances and Disease Registry, Department of Health and Human Services, CRC Press.
9. Baynes, R. E., Halling, K. B., Riviere, J. E. (1997). The influence of diethyl-m-toluamide (DEET) on the percutaneous absorption of permethrin and carbaryl. Toxicol. Appl. Pharmacol. 144:332-339.
10. Baynes, R. E., Brooks, J. D., Riviere, J. E. (2000). Membrane transport of naphthalene and dodecane in jet fuel mixtures. Toxicol. Ind. Health 16:225-238.
11. Baynes, R. E., Brooks, J. D., Budsaba, K., Smith, C. E., Riviere, J. E. (2001). Mixture effects of JP-8 additives on the dermal disposition of jet fuel components. Toxicol. Appl. Pharmacol. 175:269-281.
12. Black, R. M., Read, R. W. (1995). Biological fate of sulfur mustard, 1,1′-thiobis(2-chloroethane): identification of b-lyase metabolites and hydrolysis products in human urine. Xenobiotica 25:167-173.
13. Black, R. M., Brewster, K., Clarke, R. J., Hambrook, J. L., Harrison, J. M., Howells, D. J. (1992a). Biological fate of sulfur mustard, 1,1′-thiobis(2-chloroethane): isolation and identification of urinary metabolites following intraperitoneal administration to rats. Xenobiotica 22:405-418.
14. Black, R. M., Hambrook, J. L., Howells, D. J., Read, R. W. (1992b). Biological fate of sulfur mustard, 1,1′-thiobis(2-chloroethane): urinary excretion profiles of hydrolysis products and b-lyase metabolites of sulfur mustard after cutaneous application to rats. J. Anal. Toxicol. 16:79-84.
15. Bloomquist, J. R. (1993). In: Roe, R. M., Kuhr, R. J., eds. Neuroreceptor Mechanisms in Pyrethroid Mode of Action and Resistance. Rev. Pestic. Toxicol. Vol. 2. Raleigh, NC: Toxicology Communications.
16. Brimfield, A. A. (1995). Possible protein phosphatase inhibition by bis(hydroxyethylsulfide), a hydrolysis product of mustard gas. Toxicol. Lett. 78:43-48.
17. Brimfield, A. A., Sartori, D. A., Novak, M. J. (2002). Thiodiglycol metabolism by alcohol dehydrogenase using NMR: two-step oxidation produces α-hydroxyethyl thioacetic acid and 2 moles of NADH. The Toxicologist 66(1S):230.
18. Bruckner, J. V., Warren, D. A. (2001). Toxic effects of solvents and vapors. In: Klaassen, C. D., ed. Cassarett and Doull's Toxicology: the Basic Science of Poisons. 6th ed. McGraw-Hill: New York, pp. 869-916.
19. Buchholz, B. A., Pawley, N. H., Vogel, J. S., Mauthe, R. J. (1997). Pyrethroid decrease in central nervous system from nerve agent pretreatment. J. Appl. Toxicol. 17:231-234.
20. Buckpitt, A. R., Bahnson, L. S. (1986). Naphthalene metabolism by human lung microsomal enzymes. Toxicology 41:333-341.
21. Buckpitt, A. R., Richieri, P. (1984). Comparative Biochemistry and Metabolism: Part 2. Naphthalene Lung Toxicity. Wright-Patterson Air Force Base, OH: Air Force Systems Command, Aerospace Medical Division, Air Force Aerospace Medical Research Laboratory. AFAMRL-TR 84-058 (cited in ATSDR, 1995).
22. Buonarati, M., Jones, A. D., Buckpitt, A. R. (1990). In vivo metabolism of isomeric naphthalene oxide glutathione conjugates. Drug Metab. Dispos. 18:183-189.
23. Buratti, F. M., Volpe, M. T., Meneguz, A., Vitozzi, L., Testai, E. (2003). CYP-specific bioactivation of four phosphorothioate pesticides by human liver microsomes. Toxicol. Appl. Pharmacol. 186:143-154.
24. Butler, A. M., Murray, M. (1997). Biotransformation of parathion in human liver: participation of CYP3A4 and its inactivation during microsomal parathion oxidation. J. Pharmacol. Exp. Ther. 280:966-973.
25. Cantalamessa, F. (1993). Acute toxicity of 2 pyrethroids, permethrin and cypermethrin in neonatal and adult rats. Arch. Toxicol. 67:510-513.
26. Chambers, H., Brown, B., Chambers, J. E. (1990). Noncatalytic detoxication of six organophosphorus compounds by rat liver homogenates. Pestic. Biochem. Physiol. 36:308-316.
27. Chaney, L. A., Rockhold, R. W., Mozingo, J. R., Hume, A. S. (1997). Potentiation of pyridostigmine bromide toxicity in mice by selected adrenergic agents and caffeine. Vet. Hum. Toxicol. 39:214-219.
28. Chen, C. S., Yoshida, A. (1991). Enzymatic properties of the protein encoded by newly cloned human alcohol dehydrogenase ADH6 gene. Biochem. Biophys. Res. Commun. 181:743-747.
29. Chin, B. H., Eldridge, J. M., Sullivan, L. J. (1974). Metabolism of carbaryl by selected human tissues using an organ-maintenance technique. Clin. Toxicol. 7:37-56.
30. Cho, T., Hodgson, E., Rose, R. L. (2004). In vitro human metabolism of naphthalene. unpublished results.
31. Choi, J., Rose, R. L., Hodgson, E. (2002). In vitro human metabolism of permethrin: the role of human alcohol and aldehyde dehydrogenases. Pestic. Biochem. Physiol. 73:117-128.
32. Choi, J., Rose, R. L., Hodgson, R. L. (2004). Chlorpyrifos oxon and carbaryl inhibition of transpermethrin hydrolysis in human liver fractions. Drug Metab. Drug Interac. 20: at press.
33. Cooper, J. R., Mattie, D. R. (1996). Developmental toxicity of JP-8 fuel in the rat. J. Appl. Toxicol. 16:197-200.
34. Costa, L. G., McDonald, B. E., Murphy, S. D., Omenn, G. S., Richter, S. J., Motulsky, A. G., Furlong, C. E. (1990). Serum paraoxonase and its influence on paraoxon and chlorpyrifosoxon toxicity in rats. Toxicol. Appl. Pharmacol. 103:66-76.
35. Cranmer, M. F. (1986). Carbaryl: a toxicological review and risk analysis. Neurotoxicology 7:247-332.
36. Crofton, K. M., Reiter, L. W. (1988). The effects of type-1 and type-II pyrethroids on motor-activity and the acoustic startle response in the rat. Fundam. Appl. Toxicol. 10:624-634.
37. Dai, D., Tang, J., Rose, R. L., Hodgson, E., Bienstock, R. J., Mohrenweiser, H. W., Goldstein, J. A. (2001). Identification of variants of CYP3A4 and characterization of their abilities to metabolize testosterone and chlorpyrifos. J. Pharmacol. Exp. Ther. 299:825-831.
38. Davies, H. G., Richter, R. J., Keifer, M., Broomfield, C. A., Sowalla, J., Furlong, C. A. (1996). The effect of the human serum paraoxanase polymorphism is reversed with diazoxon, somam and sarin. Nat. Genet. 14:334-336.
39. Donato, M. T., Viitala, P., Rodriguez-Antona, C., Lindfors, A., Castell, J. V., Raunio, H., Gomez-Lechon, M. J., Pelkonen, O. (2000). CYP2A5/CYP2A6 expression in mouse and human hepatocytes treated with various inducers. Drug Metab. Dispos. 28:1321-1326.
40. Dorough, H. W. (1970). Metabolism of insecticidal methylcarbamates in animals. J. Agric. Food Chem. 18:1015-1022.
41. Dorough, H. W., Casida, J. E. (1964). Nature of certain carbamate metabolites of the insecticide Sevin. J. Agric. Food Chem. 12:294-304.
42. Dorough, H. W., Leeling, N. C., Casida, J. E. (1963). Nonhydrolytic pathway in metabolism of N-methylcarbamate insecticides. Science 140:170-171.
43. Dudley, B. F., Brimfield, A. A., Winston, G. M. (2000). Oxidation of thiodiglycol (2,2́-thiobis-ethanol) by alcohol dehydrogenase: comparison of human isoforms. J. Biochem. Molec. Toxicol. 14:244-251.
44. Dudley, A. C., Peden-Adams, M. M., EuDaly, J., Pollenz, R. S., Keil, D. E. (2001). An aryl hydrogen receptor independent mechanism of JP-8 jet fuel immunotoxicity in Ah-responsive and Ah-nonresponsive mice. Toxicol. Sci. 59:251-259.
45. Echobicon, D. J. (2001). Toxic effects of pesticides. In: Klaassen, C. D., ed. Cassarett and Doull's Toxicology: the Basic Science of Poisons. 6th ed. New York: McGraw-Hill, pp. 763-810.
46. Edwards, J. E., Rose, R. L., Hodgson, E. (2004a). In vitro metabolism of nonane by human liver microsomes and cytochrome P450 isoforms. Drug Metab. Rev. (ISSX abstract) in press.
47. Edwards, J. E., Rose, R. L., Hodgson, E. (2004b). In vitro human metabolism of nonane. unpublished results.
48. Ehrich, M., Correll, L., Strait, J., McCain, W., Wilcke, J. (1992). Toxicity and toxicokinetics of carbaryl in chickens and rats: a comparative study. J. Toxicol. Environ. Health 36:411-423.
49. Elliott, M. (1976). In: Metcalf, R. L., McKelvey, J. J., Jr., eds. Insecticides for the Future: Needs and Prospects. New York: Wiley.
50. Elliott, M., Farnham, A. W., Jones, N. F., Needham, P. H., Pulman, D. A., Stevenson, J. H. (1973). A photostable pyrethroid. Nature 246:169-170.
51. Elliott, M., Janes, N. F., Pulman, D. A., Gaughan, L. C., Unai, T., Casida, J. E. (1976). Radiosynthesis and metabolism in rats of the IR isomers of the insecticide permethrin. J. Agric. Food Chem. 24:270-276.
52. Fukuto, T. R. (1990). Mechanism of action of organophosphorus and carbamate insecticides. Environ. Health Perspect. 87:245-254.
53. Furlong, C. E. (2000). PON1 status and neurologic symptom complexes in Gulf War veterans. Genome Res. 10:153-155.
54. Furlong, CE., Costa, L. G., Hassett, C., Richter, R. J., Sundstrom, J. A., Adler, D. A., Disteche, C. M., Omiecinski, C. J., Chapline, C., Crabb, J. W., Humbert, R. (1993). Human and rabbit paraoxonases: purification, cloning, sequencing, mapping and role of polymorphism in organophosphate detoxication. Chem.-Biol. Interact. 87:35-48.
55. Furlong, C. E., Li, W. F., Costa, L. G., Richter, R. J., Shih, D. M., Lusis, A. J. (1998). Genetically determined susceptibility to organophosphorus insecticides and nerve agents: developing a mouse model for the human PON1 polymorphism. Neurotoxicology 19:645-650.
56. Garcia-Closas, M., Egan, K., Abruzzo, J., Newcomb, P., Titus-Ernstoff, L., Franklin, T., Bender, P., Beck, J., Le Marchand, L., Lum, A., Alavanja, M., Hayes, R., Rutter, J., Buetow, K., Brinton, L., Rothman, N. (2001). Collection of genomic DNA from adults in epidemiologic studies by buccal cytobrush and mouthwash. Cancer Epidemiol. Biomark. 10:687-696.
57. Gaughan, L. C., Unai, T., Casida, J. E. (1977). Permethrin metabolism in rats. J. Agric. Food Chem. 25:9-17.
58. Gillette, J. S., Hansen, L. G., Rose, R. L. (2002). Metabolic effects of episodic polychlorinated biphenyl (PCB) congeners. Rev. Toxicol. 4:129-159.
59. Grant, G. M., Shaffer, K. M., Kao, W. Y., Stenger, D. A., Pancrazio, J. J. (2000). Investigation of in vitro toxicity of jet fuels JP-8 and Jet A. Drug Chem. Toxicol. 23:279-291.
60. Guengerich, F. P., Kim, D. H., 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.
61. Haley, R. W., Kurt, T. L. (1997). Self-reported exposure to neurotoxic chemical combinations in the Gulf War - a cross sectional epidemiologic study. J. Am. Med. Assoc. 277:231-237.
62. Haley, R. W., Billecke, S., LaDu, B. N. (1999). Association of low PON1 type Q (type A) arylesterase activity with neurologic symptom complexes in Gulf War veterans. Toxicol. Appl. Pharmacol. 157:227-233.
63. Hardt, J., Angerer, J. (2003). Biological monitoring of workers after the application of insecticidal pyrethroids. Int. Arch. Occup. Environ. Health 76:492-498.
64. Harris, D. T., Sakiestewa, D., Robledo, R. F., Young, R. S., Witten, M. (2000). Effects of short-term JP-8 jet fuel exposure on cell-mediated immunity. Toxicol. Ind. Health 16:78-84.
65. Hartley, D. P., Klaassen, C. D. (2000). Detection of chemical-induced differential expression of rat hepatic cytochrome P450 mRNA transcripts using branched signal amplification technology. Drug Metab. Dispos. 28:608-616.
66. Hodgson, E. (2003). In vitro human phase I metabolism of xenobiotics I: pesticides and related compounds used in agriculture and public health, 2003. J. Biochem. Mol. Toxicol. 17:201-206.
67. Hodgson, E., Casida, J. E. (1960). Biological oxidation of N,N-dialkyl carbamates. Biochim. Biophys. Acta 42:184-186.
68. Hodgson, E., Casida, J. E. (1961). Metabolism of N,N-dialkyl carbamates and related compounds by rat liver. Biochem. Pharmacol. 8:179-191.
69. Hodgson, E., Smart, R. C. (2001). An Introduction to Biochemical Toxicology. New York: John Wiley and Sons.
70. Horning, M. G., Stillwell, W. G., Griffin, G. W., Tseng, W. S. (1980). Epoxide intermediates in the metabolism of naphthalene in the rat. Drug Metab. Dispos. 8:404-414.
71. Institute of Medicine. (2003). Gulf War and Health, Volume 1: Depleted Uranium, Pyridostigmine Bromide, Sarin, Vaccines; and 2: Insecticides and Solvents. Washington, DC: Institute of Medicine, National Academy Press.
72. Ishmael, J., Litchfield, M. H. (1988). Chronic toxicity and carcinogenic evaluation of permethrin in rats and mice. Fundam. Appl. Toxicol. 11:308-322.
73. Joannard, F., Galisteo, M., Corcos, L., Guillouzo, A., Lagadic-Gossmann, D. (2000). Regulation of phenobarbital-induction of CYP2B and CYP3A genes in rat cultured hepatocytes: involvement of several serine/threonine protein kinases and phosphatases. Cell Biol. Toxicol. 16:325-337.
74. Johnston, G. (1995). The study of interactive effects of pollutants: a biomarker approach. Sci. Total Environ. 171:205-212.
75. Kabbar, M. B., Rogers, J. V., Gunasekar, P. G., Garrett, C. M., Geiss, K. T., Brinkley, W. W., McDougal, J. N. (2001). Effect of JP-8 jet fuel on molecular and histological parameters related to acute skin irritation. Toxicol. Appl. Pharmacol. 175:83-88.
76. Kanikkannan, N., Locke, B. R., Singh, M. (2002). Effect of jet fuels on skin morphology and irritation in hairless rats. Toxicology 175:35-47.
77. Kawamura, A., Yoshida, Y., Kimura, N., Oda, H., Kakinuma, A. (1999). Phosphorylation/dephosphorylation steps are crucial for the induction of CYP2B1 and CYP2B2 gene expression by phenobarbital. Biochem. Biophys. Res. Commun. 264:530-536.
78. Korzekwa, K. R., Krishnamachary, N., Shou, M., Ogai, A., Parise, R. R., Rettie, A. E., Gonzalez, F. J., Tracy, T. S. (1998). Evaluation of atypical cytochrome P450 kinetics with two-substrate models: evidence that multiple substrates can simultaneously bind to cytochrome P450 active sites. Biochemistry 37:4137-4147.
79. Leng, G., Kuhn, K. H., Idel, H. (1997). Biological monitoring of pyrethroids in blood and pyrethroid metabolites in urine: applications and limitations. Sci. Total Environ. 199:173.
80. Leng, G., Lewalter, J., Rohrig, B., Idel, H. (1999). The influence of individual susceptibility in pyrethroid exposure. Toxicol. Lett. 107:123-130.
81. Leo, K. U. (1997). Metabolism of Proposed Nerve Agent Pretreatment, Pyridostigmine Bromide. Walter Reed Army Institute of Research Report No. NTIS/AD-A323 848/2, Available from NTIS at 800-553-6847, Washington DC.
82. Levi, P. E., Hodgson, E. (1985). Oxidation of pesticides by purified cytochrome P450 isozymes from the mouse liver. Toxicol. Lett. 24:221-228.
83. Li, A. P., Maurel, P., Gomez-Lechon, M. J., Cheng, L. C., Jurima-Romet, M. (1997). Preclinical evaluation of drug-drug interaction potential: present status of the application of primary human hepatocytes in the evaluation of cytochrome P450 induction. Chem.-Biol. Interact. 107:5-16.
84. Li, W. F., Costa, L. G., Richter, R. J., Hagen, T., Shih, D. M., Tward, A., Lusis, A. J., Furlong, C. E. (2000). Catalytic efficiency determines the in vivo efficacy of PON1 for detoxifying organophosphorus compounds. Pharmacogenetics 10:767-779.
85. Lieber, C. S. (1997). Cytochrome P4502E1: its physiological and pathological role. Physiol. Rev. 77:515-544.
86. Litchfield, M. H. (1985). Toxicity to mammals. In: Leahey, J. P., ed. The Pyrethroid Insecticides. London: Taylor & Francis, pp. 99-150.
87. Mackell, J. V., Reiders, F., Brieger, H., et al. (1951). Acute hemolytic anemia due to ingestion of naphthalene moth balls I. Clinical aspects. Pediatrics 7:722-727.
88. Marino, M. T., Schuster, B. G., Brueckner, R. P., Lin, E., Kaminskis, A., Lasseter, K. C. (1998). Population pharmacokinetics and pharmacodynamics of pyridostigmine bromide for prophylaxis against nerve agents in humans. J. Clin. Pharmacol. 38:227-235.
89. Matsumura, F. (1975). Metabolism of carbamate insecticides. In: Matsumura, F., ed. Toxicology of Insecticides. New York: Plenum Press, pp. 228-239.
90. Maxwell, D. M., Brecht, K. M., O'Neill, B. L. (1987). The effect of carboxylesterase inhibition on interspecies differences in soman toxicity. Toxicol. Lett. 39:35-42.
91. May, D. G., Naukam, R. J., Kambam, J. R., Branch, R. A. (1992). Cimetidine-carbaryl interaction in humans: evidence for an active metabolite of carbaryl. J. Pharmacol. Exp. Ther. 262:1057-1061.
92. McCain, W. C., Lee, R., Johnson, M. S., Whaley, J. E., Ferguson, J. W., Beall, P., Leach, G. (1997). Acute oral toxicity study of pyridostigmine bromide, permethrin, and DEET in the laboratory rat. J. Toxicol. Environ. Health 50:113-124.
93. McDougal, J. N., Pollard, D. L., Weisman, W., Garrett, C. M., Miller, T. E. (2000). Assessment of skin absorption and penetration of JP-8 jet fuel and its components. Toxicol. Sci. 55:247-255.
94. Metker, L., Angerhofer, R. A., Pope, C. R., Swentzel, K. C. (1978). Toxicological Evaluation of 3-(Phenoxyphenyl)methyl (±)-cis, trans-3-(2,2-Dichloroethenyl)- 2,2-Dimethylcyclopropane Carboxylate (Permethrin). Report No. 51-0831-78, U.S. Army Environmental Hygiene Agency.
95. Minami, M., Hui, D. M., Katsumata, M., Inagaki, H., Boulet, A. (1997). Method for the analysis of the methylphosphonic acid metabolites of sarin and its ethanol-substituted analogue in urine as applied to the victims of the Tokyo sarin disaster. J. Chromatogr., B, Biomed. Sci. Appl. 695(2):237-244.
96. Minami, M., Hui, D. M., Wang, Z., Katsumata, M., Inagaki, H., Li, Q., Inuzuka, S., Mashiko, K., Yamamoto, Y., Oosuka, T., Boulet, A., Clement, J. G. (1998). Biological monitoring of metabolites of sarin and its by-products in human urine samples. J. Toxicol. Sci. 23(suppl. 2):250-254.
97. Miyamoto, J. (1976). Degradation, metabolism, and toxicity of synthetic pyrethroids. Environ. Health Perspect. 14:15-28.
98. Monteiro-Riviere, N., Inman, A., Riviere, J. (2001). Effects of high-dose and low-dose dermal exposure to Jet A, JP-8 and JP8 (100) jet fuels. J. Appl. Toxicol. 21:485-494.
99. Mutch, E., Blain, P. G., Williams, F. M. (1999). The role of metabolism in determining parathion toxicity in man. Toxicol. Lett. 107:177-187.
100. Nakajima, T., Okuyama, S., Yonekura, I., Sato, A. (1985). Effects of ethanol and phenobarbital administration on the metabolism and toxicity of benzene. Chem.-Biol. Interact. 55:23-38.
101. National Research Council. (2003). Toxicologic Assessment of Jet-Propulsion Fuel 8.
102. Neal, R. A. (1980). Microsomal metabolism of thiono-sulfur compounds: mechanisms and toxicological significance. Rev. Biochem. Toxicol. 2:131-171.
103. Nolan, R. J., Rick, D. L., Feshour, N. L., Saunders, J. H. (1984). Chlorpyrifos: pharmacokinetics in human volunteers. Toxicol. Appl. Pharmacol. 73:8-15.
104. Oonithan, E. S., Casida, J. E. (1968). Oxidation of methyl- and dimethylcarbamate insecticide chemicals by microsomal enzymes and anticholinesterase activity of the metabolites. J. Agric. Food Chem. 16:28-44.
105. Pakenham, E., Lango, J., Buonarati, M., Morin, D., Buckpitt, A. (2002). Urinary naphthalene mercapturates as biomarkers of exposure and stereoselectivity of naphthalene epoxidation. Drug Metab. Dispos. 30:247-253.
106. Pleil, J. D., Smith, L. B., Zelnick, S. D. (2000). Personal exposure to JP-8 fuel vapors and exhaust at Air Force bases. Environ. Health Perspect. 108:183-192.
107. Pons, F., Kalvet, J. H., Haag, M., Raeppel, V., Keravis, T., Frossard, N. (2001). Altered expression of lung cytochrome P450 3A1 after exposure to sulfur mustard. Pharmacol. Toxicol. 88:40-44.
108. Purdon, M. P., Lehman-McKeeman, L. D. (1997). Improved high-performance liquid chromatographic procedure for the separation and quantification of hydroxytestosterone metabolites. J. Pharmacol. Toxicol. Methods 37:67-73.
109. Ramos, G., Nghiem, D. X., Walterschied, J. P., Ullrich, S. E. (2002). Dermal application of jet fuel suppresses immune reactions. Toxicol. Appl. Pharmacol. 180:136-144.
110. Raucy, J. L., Kraner, J. C., Lasker, J. M. (1993). Bioactivation of halogenated hydrocarbons by cytochrome P4502E1. Crit. Rev. Toxicol. 23:1-20.
111. Rhyne, B. N., Pirone, J. R., Riviere, J. E., Monteiro-Riviere, N. A. (2002). The use of enzyme histochemistry in detecting cutaneous toxicity of three topically applied jet fuel mixtures. Toxicol. Mech. Methods 12:17-34.
112. Richter, R. J., Furlong, C. E. (1999). Determination of paraoxonase (PON1) status requires more than genotyping. Pharmacogenetics 9:745-753.
113. Ritchie, G. D., Still, K. R., Alexander, W. K., Nordholm, D. F., Wilson, C. L., Rossi, J., Mattie, D. R. (2001). A review of neurotoxicity risk of selected hydrocarbon fuels. J. Toxicol. Environ. Health, Part B, Crit. Rev. 4:223-312.
114. Riviere, J. E., Brooks, J. D., Monteiro-Riviere, N. A., Budsaba, K., Smith, C. E. (1999). Dermal absorption and distribution of topically dosed jet fuels Jet-A, JP-8 and JP-8(100). Toxicol. Appl. Pharmacol. 160:60-75.
115. Robertson, P., Decory, H. H., Madan, A., Parkinson, A. (2000). In vitro inhibition and induction of human hepatic cytochrome P450 enzymes by modafinil. Drug Metab. Dispos. 28:664-671.
116. Robledo, R. F., Scott Young, R., Lantz, C., Witten, M. (2000). Short-term pulmonary response to inhaled JP-8 jet fuel aerosol in mice. Toxicol. Pathol. 28:656-663.
117. Rose, R. L., Cherrington, N. (2004). Pesticide induction of xenobiotic-metabolizing enzymes in human hepatocytes. Unpublished results.
118. Sams, C., Mason, H. J., Rawbone, R. (2000). Evidence for the activation of organophosphate pesticides by cytochromes P450 3A4 and 2D6 in human liver microsomes. Toxicol. Lett. 116:217-221.
119. Schoenig, G. P., Hartnagel, R. J. Jr., Osimitz, T. G., Llanso, S. (1996). Absorption, distribution, metabolism and excretion of N,N-diethyl-m-toluamide in the rat. Drug Metab. Dispos. 24:156-163.
120. Selim, S., Hartnagel, R. J., Osimitz, T. G., Garbriel, K. L., Schoenig, G. P. (1995). Absorption, excretion and metabolism of N,N-diethyl-m-toluamide following dermal application to human volunteers. Fundam. Appl. Toxicol. 25:95-100.
121. Shih, M. L., McMonagle, J. D., Dolzine, D. W., Gresham, V. C. (1994). Metabolite pharmacokinetics of soman, sarin and GF in rats and biological monitoring of exposure to toxic organophosphorus agents. J. Appl. Toxicol. 14:195-199.
122. Smith, L. B., Bhattacharya, A., Lemasters, G., Succop, P., Puhala, E., Medvedovic, M., Joyce, J. (1997). Effect of chronic low-level exposure to jet fuel on postural balance of U.S. Air Force personnel. J. Occup. Environ. Med. 39:623-632.
123. 2 human and alcohol dehydrogenases affect hydride transfer and coenzyme dissociation rate constants. J. Biol. Chem. 268:892-899.
124. Strother, A. (1972). In vitro metabolism of methylcarbamate insecticides by human and rat liver fraction. Toxicol. Appl. Pharmacol. 21:112-129.
125. Sultatos, L. G. (1991). Metabolic activation of the organophosphorus insecticides chlorpyrifos and fenitrothion by perfused rat liver. Toxicology 68:1-9.
126. Sultatos, L. G., Pastino, G. M., Rosenfeld, C. A., Flynn, E. J. (2004). Incorporation of the genetic control of alcohol dehydrogenase into a physiologically based pharmacokinetic model for ethanol in humans. Toxicol. Sci. 78:20-31.
127. Surbrook, S. E., Olson, M. J. (1992). Dominant role of cytochrome P-450 2E1 in human hepatic microsomal oxidation of the CFC-substitute 1,1,1,2-tetrafluoroethane. Drug Metab. Dispos. 20:518-524.
128. Szinicz, L., Baskin, S. L. (1999). Chemical and biological agents. In: Marquardt, H., Schafer, S. G., McClellan, R. O., Welsch, F., eds. Toxicology. New York: Academic Press, pp. 851-877.
129. Tang, J., Cao, Y., Rose, R. L., Brimfield, A. A., Dai, D., Goldstein, J. A., Hodgson, E. (2001). Metabolism of chlorpyrifos by human cytochrome P450 isoforms and human, mouse and rat liver microsomes. Drug Metab. Dispos. 29:1201-1204.
130. Tang, J., Cao, Y., Rose, R. L., Hodgson, E. (2002). In vitro metabolism of carbaryl by human cytochrome P450 and its inhibition by chlorpyrifos. Chem.-Biol. Interact. 141:229-241.
131. Tingle, M. D., Pirmohamad, M., Templeton, E., et al. (1993). An investigation of the formation of cytotoxic, genotoxic, protein-reactive and stable metabolites from naphthalene by human liver microsomes. Biochem. Pharmacol. 46:1529-1538.
132. Tripathi, D. N., Sugendran, K., Malhotra, R. C., Bhattacharya, A., Dasgupta, S. (1995). Studies on urine and tissues of rats, guinea pigs and mice exposed to sulfur mustard using mass-spectrometry. J. Biosci. 20:29-33.
133. Ullrich, S. E., Lyons, H. J. (2000). Mechanisms involved in the immunotoxicity induced by dermal application of JP-8 jet fuel. Toxicol. Sci. 58:290-298.
134. USEPA. (1998). Toxicological Review of Naphthalene (CAS No. 91-20-3) in Support of Summary Information on the Integrated Risk Information System (IRIS). U.S. Environmental Protection Agency.
135. Usmani, K. A., Rose, R. L., Goldstein, J. A., Taylor, W. G., Brimfield, A. A., Hodgson, E. (2002). In vitro human metabolism and interactions of the repellent, N,N-diethyl-m-toluamide (DEET). Drug Metab. Dispos. 30:289-294.
136. Usmani, K. A., Rose, R. L., Hodgson, E. (2003). Inhibition and activation of the human liver and human cytochrome P450 3A4 metabolism of testosterone by deployment-related chemicals. Drug Metab. Dispos. 31:384-391.
137. Usmani, K. A., Hodgson, E., Rose, R. L. (2004). In vitro human metabolism of pyridostigmine. unpublished studies.
138. Veltri, J. C., Osimitz, T. G., Bradford, D. C., Page, B. C. (1994). Retrospective analysis of calls to poison control centers resulting from exposure to the insect repellent N,N-dielhyl-m-toluamide (DEET) from 1985 to 1989. Clin. Toxicol. 32:1-16.
139. Verschoyle, R. D., Barnes, J. M. (1972). Toxicity of natural and synthetic pyrethrins to rats. Pestic. Biochem. Physiol. 2:308-311.
140. Vodela, J. K., Dalvi, R. R. (1995). Comparative toxicological studies of chlorpyrifos in rats and chickens. Vet. Hum. Toxicol. 37:1-3.
141. Wagner, F. W., Burger, A. R., Vallee, B. L. (1983). Kinetic properties of human liver alcohol dehydrogenase: oxidation of alcohols by class I isoenzymes. Biochemistry 22:1857-1863.
142. Ward, S. A., May, D. G., Heath, A. J., Branch, R. A. (1988). Carbaryl metabolism is inhibited by cimetidine in the isolated perfused rat liver and in man. Clin. Toxicol. 26:269-281.
143. Warshawsky, D., Bingham, E., Niemeier, R. M. (1977). The effects of N-dodecane on the metabolism and distribution of benzo(a)pyrene in the isolated perfused rabbit lung. Life Sci. 27:1827-1837.
144. Winder, C., Balouet, J. C. (2002). The toxicity of commercial jet fuels. Environ. Res. 89:146-164.
145. Yuknavage, K. L., Fenske, R. A., Kalman, D. A., Keifer, M. C., Furlong, C. E. (1997). Simulated dermal contamination with capillary samples and field cholinesterase biomonitoring. J. Toxicol. Environ. Health 51:35-55.
146. Zeiger, E., Smith, L. (1998). The first international conference on the environmental health and safety of jet fuel. Environ. Health Perspect. 106:763-764.