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Parameters for Pyrethroid Insecticide QSAR and PBPK/PD Models for Human Risk Assessment

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Parameters for Pyrethroid Insecticide QSAR and PBPK/PD Models for Human Risk Assessment Parameters for Pyrethroid Insecticide QSAR and PBPK/PD Models for Human Risk Assessment (March 13, 2012) James B. Knaak*, Curtis C. Dary, Xiaofei Zhang, Robert W. Gerlach, R. Tornero-Velez, Daniel T. Chang, Rocky Goldsmith and Jerry N. Blancato J.B. Knaak* (Corresponding author: [email protected]) Department of Pharmacology and Toxicology, School of Medicine and Biomedical Sciences, SUNY at Buffalo, 3435 Main Street, Buffalo, NY 14214, USA. C.C. Dary U.S. Environmental Protection Agency, Human Exposure and Atmospheric Sciences Division, 944 East Harmon Avenue, Las Vegas, NV 89193-3478, USA. R.W. Gerlach ڄ X. Zhang General Dynamics Information Technology, 181 North Arroyo Grande Boulevard, Suite 105A, Henderson, NV 89074-1624, USA. ;R. Goldsmith, Mail Code E205-01 ڄ D. Chang ڄ R. Tornero-Velez J.N. Blancato, Mail Code B143-04 U.S. Environmental Protection Agency, National Exposure Research Laboratory, 109 T.W. Alexander Drive, Research Triangle Park, NC 27709, USA. 1 2 Contents 1 Introduction ..............................................................................................................................x 2 Nature of Pyrethrin and Pyrethroid Insecticides ......................................................................x 2.1 Discovery .......................................................................................................................x 2.2 Isomers and Technical Products ....................................................................................x 2.3 Stereochemistry..............................................................................................................x 2.4 Analytical Methods for Pyrethroid Isomers ...................................................................x 2.5 Pyrethrins, Pyrethroids, and Their Chiral Components .................................................x 2.6 Isomers of Chrysanthemic Acids ...................................................................................x 2.7 Analytical Chemistry, Acid Components ......................................................................x 2.8 Alcohol Components .....................................................................................................x 2.9 Mammalian Toxicity ......................................................................................................x 3 Experimentally-derived Absorption Parameters Used in PBPK/PD Models ...........................x 3.1 Gastrointestinal Absorption/Metabolism .......................................................................x 3.2 Enterohepatic Circulation (EHC) ...................................................................................x 3.3 Gut Metabolism/Transport…. ........................................................................................x 3.4 Skin Absorption .............................................................................................................x 3.5 Skin Permeability…………. ..........................................................................................x 3.6 Relationship between Kp (permeation constant), Skin:Air, and Skin: Vehicle Partition Coefficients……... .............................................................................x 3.7 Skin:Blood Partition Coefficients ..................................................................................x 3.8 Dermal Dose-response, Pharmacokinetic, and Metabolism Studies…………... 3 4 Mechanistic Models for Determining Tissue:Blood Partition Coefficients ..............................x 4.1 Tissue Partition Coefficients/Distribution .....................................................................x 4.2 Partition Coefficients From In Vitro Data .....................................................................x 4.3 Selection of Log Po:w and Log Do:w Values ...............................................................x 4.4 Tissue:Blood Partition Coefficients ...............................................................................x 4.5 Partition Coefficients for Pyrethroids and Metabolites .................................................x 5 In Vivo Metabolism of 15 Pyrethroid Insecticides…………….....…………………x 5.1 Allethrin…………………………………………………………..........................X 5.2 Bifenthrin………………………………………………………………………….. 5.3 Cyfluthrin…………………………………………………………………………... 5.4 Cyhalothrin………………………………………………………………………… 5.5 Cypermethrin………………………………………………………………………. 5.6 Deltamethrin……………………………………………………………………… 5.7 Fenvalerate…………………………………………………………………………. 5.8 Fenpropathrin………………………………………………………………………. 5.9 Fluvalinate………………………………………………………………………….. 5.10 Permethrin………………………………………………………………………… 5.11 Phenothrin………………………………………………………………………… 5.12 Resmethrin………………………………………………………………………... 5.13 Tefluthrin…………………………………………………………………………. 5.14 Tetramethrin………………………………………………………………………. 5.15 Tralomethrin……………………………………………………………………… 6 Metabolic Enzymes, Carboxylesterases and Cytochrome P450s .............................................x 4 6.1 Carboxylesterases (CEs) and their Multiple Forms .......................................................x 6.2 Cytochrome P450s and their Multiple Forms ................................................................x 6.3 Hydrolysis of Pyrethroids by CEs..................................................................................x 6.4 In Vitro Metabolism ......................................................................................................x 6.5 Binding of Substrates to Microsomes and CYPs; Prediction of Km and Vmax ...................... x 7 QSAR Models for Predicting Biological Parameters Used in PBPK/PD Models ........................x 7.1 Toxicity Models... 7.2 QSAR Models for Predicting the Binding of Pyrethroids to Plasma and Hepatic Proteins... 7.3 Intestinal Permeability ...................................................................................................x 7.4 Liver P450 CYP Hydroxylation Models.........................................................x 7.5 Comparison of Predicted vs. Experimental Vmax and Km Values .................................x 7.6 Prediction of Liver and Plasma Carboxylesterase Activity ...........................................x 7.7 Conjugation of Intact Pyrethroids and Aromatic Leaving Groups ................................x 7.8 Skin Permeation Constants ............................................................................................x 7.9 Tissue:Blood Partition Coefficients; QSAR Models .....................................................x 8 Lipids, Target Proteins and Ion Channels ................................................................................x 8.1 Biomembranes and Ion Channels ..................................................................................x 8.2 Patch Clamp Technique .................................................................................................x 8.3 Voltage Dependence and Kinetics of Activation and Inactivation ................................x 8.4 Atomic Force Microscopy .............................................................................................x 8.5 Effective Concentrations for Altering Sodium Channels ..............................................x 8.6 Sodium Channel Modifications .....................................................................................x 5 8.7 Mitochondrial Complex in Neurotoxicity ......................................................................x 9 Neurotoxicity ............................................................................................................................x 9.1 Functional Observation Batteries (FOB) .......................................................................x 9.2 Na+1 Ion Channels ..........................................................................................................x 9.3 Ca+2 Ion Channels ..........................................................................................................x 9.4 Cl-1 Ion Channels ...........................................................................................................x 9.5 Developmental Neurotoxicity ........................................................................................x 10 Discussion ................................................................................................................................x 11 Recommendations ... 12 Summary ....................................................................................................................................x Acknowledgements ..........................................................................................................................x References ........................................................................................................................................x Appendix A: Nomenclature ..........................................................................................................x i. Acronyms and Abbreviations ii. Chemical and Mathematical Expressions Appendix B: Pyrethroids, Pyrethroid Isomers and Technical Products ........................................x Appendix C: Chromatographic Separation of Pyrethroids and Their Isomers ..............................x Appendix D: Chemical Structures, Physical Parameters, and Tissue:Partition Coefficients of Parent Pyrethroids and Metabolites ................................................x Appendix E: Metabolic Pathways and Preliminary Metabolic Rate Constants (Vmax and Km) for the Metabolism of Parent Pyrethroids and Metabolites .............x
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