Abstract
This pyrethroid insecticide parameter review is an extension of our interest in developing quantitative structure–activity relationship–physiologically based pharmacokinetic/pharmacodynamic (QSAR-PBPK/PD) models for assessing health risks, which interest started with the organophosphorus (OP) and carbamate insecticides (Knaak et al. 2004, 2008). The parameters shown in Table 1 (Blancato et al. 2000) are needed for developing pyrethroid PBPK/PD models, as is information on the metabolic pathways of specific pyrethroids in laboratory test animals and humans. Parameters may be obtained by fitting the output from models to experimental data gathered from in vivo studies (Zhang et al. 2007; Nong et al. 2008), in conjunction with using (1) experimental data obtained from in vitro studies, (2) quantitative structure–activity relationships (QSAR) and (3) other mathematical models, such as the mechanistic Poulin-Theil (2000; 2002a; b) algorithms for obtaining blood:tissue partition coefficients.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Abernathy CO, Casida JE (1973) Pyrethroid insecticides: esterase cleavage in relation to selective toxicity. Science 179:1235–1236
Ackermann P, Bourgeois F, Drabek J (1980) The optical isomers of alpha-cyano-3-phenoxybenzyl 3-1,2-dibromo-2,2-dichloroethyl-2,2-dimethylcyclopropanecarboxylate and their insecticidal activities. J Pestic Sci 11:169–179
Agoram B, Woltosz WS, Bolger MB (2001) Predicting the impact of physiological and biochemical processes on oral drug bioavailability. Adv Drug Deliver Rev 50:S41–S67
Allen S, Leah A (1990) Lambda-cyhalothrin: acute oral toxicity study in the rat. Zeneca Agricultural Products Laboratory No. CTL/P/3209:AR4840, Wilmington, DE.
Anadon A, Martinez-Larranaga MR, Fernandez-Cruz ML, Diaz MJ, Fernadez MC, Martinez MA (1996) Toxicokinetics of deltamethrin and its 4′-OH-metabolite in the rat. Toxicol Appl Pharmacol 141:8–16
Anand SS, Bruckner JV, Haines WT, Muralidhara S, Fisher JW, Padilla S (2006) Characterization of deltamethrin metabolism by rat plasma and liver microsomes. Toxicol Appl Pharmacol 212:156–166
Andersen ME, Dennison JE (2001) Mode of action and tissue dosimetry in current and future risk assessments. Sci Total Environ 274(1–3):3–14
Angerer J, Ritter A (1997) Determination of metabolites of pyrethroids in human urine using solid-phase extraction and gas chromatography-mass spectrometry. J Chromatogr 695:217–226
Artursson P, Palm K, Luthan K (1996) Caco-2 monolayers in experimental and theoretical predictions of drug transport. Adv Drug Deliv Rev 22:67–84
Audegond L, Collas E, Glomot R (1981a) RU 25474 (tralomethrin) single administration study by oral route in the rat. Study No. RU-4BE-81.240/A, Roussel-Uclaf, Paris.
Audegond L, Collas E, Glomot R (1981b) RU 25474 (tralomethrin) single administration study by oral route in the rat. Study No. 81240 DS/84/A, Roussel-Uclaf, Paris.
Austin RP, Barton P, Cockroft SL, Wenlock MC, Riley RJ (2002) The influence of nonspecific microsomal binding on apparent intrinsic clearance, and its prediction from physicochemical properties. Drug Metab Dispos 30:1497–1503
Baker H, Kligman AM (1967) Measurement of transepidermal water loss by electrical hygrometry. Arch Dermatol 96:441–452
Barbero AM, Frasch HF (2009) Pig and guinea pig skin as surrogates for human in vitro penetration studies: a quantitative review. Toxicol In Vitro 23:1–13
Barrueco D, Herrera A, Caballo C, Delapena E (1992) Cytogenic effects of permethrin in cultured human-lymphocytes. Mutagenesis 7:433–437
Barter ZE, Bayliss MK, Beaune PH, Boobis AR, Carlile DJ, Edwards RJ, Houston JB, Lake BG, Lipscomb JC, Pelkonen OR, Tucker GT, Rostami-Hodjegan A (2007) Scaling factors for the extrapolation of in vivo metabolic drug clearance from in vitro data: reaching a consensus on values of human microsomal protein and hepatocellularity per gram of liver. Curr Drug Metab 8:33–45
Bast GE, Taeschner D, Kampffmeyer HG (1997) Permethrin absorption not detected in single-pass perfused rabbit ear, and absorption with oxidationof 3-phenoxybenzyl alcohol. Arch Toxicol 71:179–186
Baynes RE, Halling KB, Riviere JE (1997) The influence of Diethyl-m-toluamide (DEET) on the percutaneous absorption of permethrin and carbaryl. Toxicol Appl Pharmacol 144:332–339
Berenson GS, Burch GE (1951) Studies of diffusion through dead human skin. Am J Trop Med Hyg 31:842–853
Berezhkovskly LM (2004a) Determination of volume of distribution at steady state with complete consideration of the kinetics of protein and tissue binding in linear. J Pharm Sci 93:364–364
Berezhkovskly LM (2004b) Volume of distribution at steady state for a linear pharmacokinetic system with peripheral elimination. J Pharm Sci 93:1628–1640
Berezhkovskly LM (2007) The connection between the steady state (Vss) and Terminal (Vβ) volumes of distribution in linear pharmacokinetics and the general proof that Vβ ≥ Vss. J Pharm Sci 96:1638–1650
Bilsback MM, Parker CM, Wimberly HC (1984) Comparative oral toxicity of technical MO70616 and technical SD 42775 in rats. Study No. WRC-RIR 357.Corporation Study No. NCT584.01, Shell Development Company, Houston, TX.
Blancato JN, Knaak JB, Power F (2000) Use of PBPK models for assessing absorbed dose and ChE inhibition from aggregate exposure of infants and children to organophosphorous insecticides. Presented at 10th Annual Meeting of the International Society of Exposure Analysis, Monterey, CA (Abstract 3F-09o)
Bloomquist JR, Soderlund DM (1988) Pyrethroid insecticides and DDT modify alkaloid-dependent sodium channel activation and its enhancement by sea anemone toxin. Mol Pharmacol 33:543–550
Boatman RJ, Knaak JB (2001) Ethers of ethylene glycol and derivatives. In: Bingham E, Cohrsson B, Powell CH (eds) Patty’s toxicology (5th ed). Wiley, NY, NY
Bolger MB (2010) Simulations-Plus, Inc., Lancaster, CA. Memo to Kurt Enslein, Enslein Research, Rochester, NY.
Breckenridge CB, Holden L, Sturgess N, Weiner M, Sheets L, Sargent D, Soderlund DM, Choi J-S, Symington S, Clark JM, Burr S, Ray D (2009) Evidence for a separate mechanism of toxicity for the Type I and the Type II pyrethroid insecticides. Neurotoxicology 30(Suppl 1):S17–S31
Bronaugh RL, Stewart RF, Congdon ER (1982) Methods for in vitro percutaneous absorption studies II. Animal models for human skin. Toxicol Appl Pharmacol 62:481–488
Bronaugh RL, Stewart RF, Simon M (1986) Methods for in vitro percutaneous absorption studies. VII: use of excised human skin. J Pharm Sci 75:1094–1097
Brown RP, Delp MD, Lindstedt SL, Rhomberg LR, Beliles RP (1997) Physiological parameter values for physiologically based pharmacokinetic models. Toxicol Ind Health 13:407–484
Burr SA, Ray DE (2004) Structure-activity and interaction effects of 14 different pyrethroids on voltage-gated chloride ion channels. Toxicol Sci 77:341–346
Cahn RS, Ingold CK, Prelog V (1966) Specification of chirality. Angew Chem Int Ed Engl 5:385–415
Casida JE, Kimmel EC, Elliott M, Janes NF (1971a) Oxidative metabolism of pyrethrins in mammals. Nature 230:326–327
Casida JE, Kimmel ED, Elliott M, Janes NF (1971b) Oxidative metabolism of pyrethrins in mammals. Pyrethrum Post 11:58–59
Casida JE, Ueda K, Gaughan LC, Jao LT, Soderlund DM (1975) Structure-biodegradability relationships in pyrethroid insecticides. Arch Environ Contam Toxicol 3:491–500
Cayley GR, Simpson BW (1986) Separation of pyrethroid enantiomers by chiral high-performance liquid chromatography. J Chromatogr A 356:123–134
Chamberlain K, Matsuo N, Kaneko H, Khambay BPS (1998) Pyrethroids. In: Chirality in agrochemicals. Wiley, New York
Chang JH, Benet LZ (2005) Glucuronidation and the transport of the glucuronide metabolites in LLC-PK1 cells. Mol Pharmacol 2:428–434
Chang SK, Brooks JB, Monteiroriviere NA, Riviere JE (1995) Enhancing or blocking effect of fenvalerate on the subsequent percutaneous absorption of pesticides in vitro. Pestic Biochem Physiol 51:214–219
Chang DT, Goldsmith M-R, Tornero-Velez L-J, Ulrich E, Lindstrom AB, Dary CC (2009) A novel application of QSAR and PH4 models for the elucidation of the stereoselective hydrolysis rates of pyrethroids by rat serum carboxylesterase. Society of Environmental Toxicology and Chemistry, New Orleans, LA, November 2009 meeting.
Chemical Abstracts Service (2002) Chemical abstracts 2002 index guide, appendix IV, naming and indexing of chemical substances for chemical abstracts, E. Stereochemistry and stereoparents (paragraphs 202–212). Chemical Abstracts Service, Columbus, Ohio.
Choi J-S, Soderlund DM (2006) Structure-activity relationships for the action of 11 pyrethroid insecticides on rat Nav1.8 sodium channels expressed in Xenopus oocytes. Toxicol Appl Pharmacol 211:233–244
Clark JM, Brooks MW (1989) Role of ion channels and intraterminal calcium homeostasis in the action of deltamethrin at presynaptic nerve terminals. Biochem Pharmacol 38:2233–2245
Class TJ, Ando T, Casida JE (1990) Pyrethroid metabolism: microsomal oxidase metabolites of (S)-bioallethrin and the six natural pyrethrins. J Agric Food Chem 38:529–537
Cole LM, Ruzo LO, Wood EJ, Casida JE (1982) Pyrethroid metabolism: comparative fate in rats of tralomethrin, tralocythrin, deltamethrin, and (1R, alphaS)-cis-cypermethrin. J Agric Food Chem 30:631–636
Colmenarejo G (2003) In silico prediction of drug-binding strengths to human serum albumin. Med Res Rev 23:275–301
Colmenarejo G, Alverez-Pedraglio A, Lavandera J (2001) Cheminformatic models to predict binding affinities to human serum albumin. J Med Chem 44:4370–4378
Cramer RD, Patterson DE, Bunce JD (1988) Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110:5959–5967
Crane AL, Browner RW, Knaak JB, Bonner MR, Fenske RA, Farahat FM, Anger WK, Lein PJ, Olson JR (2011) Inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) in human blood following in vitro and in vivo exposure to chlorpyrifos. Abstract No. 1243, 49th Annual Meeting and ToxExpo, Salt Lake City, Utah, March 7–11.
Crawford MJ, Hutson DH (1977) The metabolism of the pyrethroid insecticide (±)-α-cyano-3-phenoxybenzyl 2, 2, 3, 3-tetramethylclyclopropanecarboxylate, WL 41706, in the rat. Pestic Sci 8:579–599
Crawford MJ, Croucher A, Hutson DH (1981a) Metabolism of cis- and trans-cypermethrin in rats. Balance and tissue retention study. J Agric Food Chem 29:130–135
Crawford MJ, Croucher A, Hutson DH (1981b) The metabolism of the pyrethroid insecticide cypermethrin in rats: excreted metabolites. Pestic Sci 12:399–411
Crow JA, Borazjani A, Potter PM, Ross MK (2007) Hydrolysis of pyrethroids by human and rat tissues: examination of intestinal, liver and serum carboxylesterases. Toxicol Appl Pharmacol 221:1–12
Culliford SJ, Borg JJ, O’Brien MJ, Kozlowski RZ (2004) Differential effects of pyrethroids on volume-sensitive anion and organic osmolyte pathways. Clin Exp Pharmacol Physiol 31:134–144
Danker T, Mazzanti M, Tonini R, Rakowska A, Oberleithner H (1997) Using the atomic force microscopy to investigate patch-clamped nuclear membrane. Cell Biol Int 21:747–757
Davies B, Morris T (1993) Physiological parameters in laboratory animals and humans. Pharm Res (NY) 10:1093–1095
Delie F, Rubas W (1997) A human colonic cell line sharing similarities with enterocytes as a model to examine oral absorption: advantages and limitations of the Caco-2 model. Crit Rev Ther Drug Carrier Syst 14:221–286
L’Hoste J (ed) (1982) Deltamethrin monograph. Roussel-Uclaf, Paris
Diel F, Detscher M, Schock B, Ennis M (1998) In vitro effects of the pyrethroid S-bioallethrin on lymphocytes and basophils from atopic and nonatopic subjects. Allergy 53:1052–1059
Eadsforth CV, Baldwin MK (1983) Human dose-excretion studies with pyrethroid insecticide, cypermethrin. Xenobiotica 13:67–72
Eadsforth CV, Bragt PC, Sittert NJ (1988) Human dose-excretion studies with pyrethroid insecticides: cypermethrin and alpha cypermethrin: relevance for biological monitoring. Xenobiotica 18:603–614
EC-HCPDG (2002) European Commission, Health & Consumer Protection Directorate-General, Directorate E1: Plant Health. Beta-Cyfluthrin, Review Report # 6841/VI/97-final, 12-2-2002.
Eells JT, Bandettini PA, Holman PA, Propp JM (1992) Pyrethroid insecticide-induced alterations in mammalian synaptic membrane-potential. J Pharmacol Exp Ther 262:1173–1181
Eldefrawi ME, Sherby SM, Abalis IM, Eldefrawi AT (1985) Interactions of pyrethroid and cyclodiene insecticides with nicotinic acetylcholine and GABA receptors. Neurotoxicology 6:47–62
Elflein L, Berger-Preiss E, Preiss A, Elend M, Levsen K, Wunsch G (2003) Human biomonitoring of pyrethroid insecticides used indoors: determination of the metabolites E-cis/trans-chrysanthemum dicarboxylic acid in human urine by gas chromatography-mass spectrometry with negative chemical ionizations. J Chromatogr B 795:195–207
Elliott M (1989) The pyrethroids: early discovery, recent advances and the future. Pestic Sci 27:337–351
Elliott M, Janes NF (1978) Synthetic pyrethroids: a new class of insecticide. Chem Soc Rev 7:473–505
Elliott M, Farnham AW, Janes NF, Needham PH, Pearson BC (1967) 5-Benzyl-3-furylmethyl chrysanthemate a new potent insecticide. Nature (London) 213:493–494
Elliott M, Janes NF, Kimmel EC, Casida JE (1972) Metabolic fate of pyrethrin I, pyrethrin II, and allethrin administered orally to rats. J Agric Food Chem 20:300–313
Elliott M, Farnham AW, Janes NF, Needhan DH, Pulman DA (1974) Synthetic insecticides with a new order of activity. Nature (London) 248:710–711
Elliott M, Janes NF, Pulman DA, Gaughan LC, Unai T, Casida JE (1976) Radiosynthesis and metabolism in rats of the 1R-isomers of the insecticide permethrin. J Agric Food Chem 24:270–276
Elliott M, Janes NF, Potter C (1978) The future of pyrethroids in insect control. Ann Rev Entomol 23:443–469
Ellison CA, Knaak, JB, McDougall R, Lein PJ, Farahat FM, Anger WK, Olson JR (2011) Construction and validation of a human PBPK/PD model for dermal chlorpyrifos exposure utilizing human biomarker data. Abstract No. 2106, 50th Annual Meeting and ToxExpos, Washington, DC, March 6–10.
Enan E, Matsumura F (1993) Activation of phosphoinositide protein-kinase-c pathway in rat-brain tissue by pyrethroids. Biochem Pharmacol 45:703–710
Enslein K (2010) ADMET predictor. Simulations-Plus, Lancaster, CA
Enslein K, Gombar VK, Shapiro D, Blake BW (1998) Prediction of rat oral LD50 values of chemicals by QSAR equations. TOPKAT Health Designs, Rochester, NY
Enslein K, Knaak JB, Van Nostrand K, Susa R, Koestler D (2007) CYP3A4 hydroxylation kinetics: QSAR models with application to PBPK modeling. J Comput Aided Mol Des. An internal document-Enslein Research, Inc., Rochester, NY. (submitted).
Farahat FM, Ellison CA, Bonner MR, McGarrigle BP, Crane AL, Fenske RA, Lasarev MR, Rohlman DS, Anger WK, Lein PJ, Olson JR (2011) Biomarkers of chlorpyrifos exposure and effect in Egyptian cotton field workers. Environ Health Perspect 119:801–816
Farahmand S, Maibach HI (2009) Estimating skin permeability from physicochemical characteristics of drugs: a comparison between conventional models and an in vivo-based approach. Int J Pharm 375:41–47
Faraoni M, Messina A, Polcaro CM, Aturki Z, Sinibaldi M (2004) Chiral separation of pesticides by coupled-column liquid chromatography application to the stereoselective degradation of fenvalerate in soil. J Liq Chromatogr Rel Technol 27:995–1012
Feldmann RJ, Maibach HI (1974) Percutaneous penetration of some pesticides and herbicides in man. Toxicol Appl Pharmacol 28:126–132
Fisher JB, Debray PH, Robinson J (1983) In: Plant Protection for Human Welfare, Proc 10th Internat Congr Plant Prot Vol 1, BCPC, Croydon, UK, 1983, pp 452–459. FMC, U.S. Patent 4,262,921 (1981)
Fleischer R (1877) Untersuchgen uber das resporptions-vermogen der menschlichen haut. Erlangen 1877. Habilitationsschrift p 81.
Flynn GL (1990) Physicochemical determinants of skin absorption. In: Gerrity TR, Henry CJ (eds) Principles of route-to-route extrapolation for risk assessment. Elsevier, New York, pp 93–127
Foxenberg RJ, Knaak JB, McGarrigle BP, Kostyniak PJ, Olson JR (2007) Human hepatic cytochrome P450-specific metabolism of parathion and chlorpyrifos. Drug Metab Dispos 35:189–193
Foxenberg RJ, Ellison CA, Knaak JB, Ma C, Olson JR (2011) Cytochrome P450-specific human PBPK/PD models for the organophosphorus pesticides: chlorpyrifos and parathion. Toxicology 285:57–66
Freeman C (1982) Acute oral toxicity study in rats: FMC 54800. Study No. A83-859, FMC Corporation, Philadelphi PA.
Freeman C (1987) Acute oral toxicity study-FMC 45806 technical: Study No. A87-2282, FMC Corporation, Philadelphia, PA.
Freeman C (1989) Acute oral toxicity of FMC 56701 technical in rats. Study No. A89-2914, FMC Corporation, Philadelphia, PA.
Fujikawa M, Nakao K, Shimizu R, Akamatsu M (2007) QSAR study on permeability of hydrophobic compounds with artificial membranes. Bioorg Med Chem 15:3756–3767
Fujimoto K, Itaya N, Okuno Y, Kadota T, Yamaguchi T (1973) A new insecticidal pyrethroid ester. Agric Biol Chem 37:2681–2682
Furnax R, Audegond L (1985a) Bioallethrin (synthetic) acute oral toxicity in rat. Study No. 84324/5635/5637, Roussel-Uclaf, Paris.
Furnax R, Audegond L (1985b) RU 16121 acute oral toxicity in rat. Study No. 84327/5640/5641, Roussel-Uclaf, Paris.
Gabriel D (1992) Acute oral toxicity study in rats. Study No. 92-7529A, Pyrethrin Joint Venture Chemical Specialties Manufacturing Association, Washington, DC.
Gao R, Zhu L, Chen Z (1998) Separation of pyrethroid enantiomers of fenpropathrin and fluvalinate by chiral high performance liquid chromatography. Nongyao (Pesticides) 37(9):22–24
Gargas ML, Burgess RJ, Voisard DE, Cason GH, Andersen ME (1989) Partition coefficients of low-molecular-weight volatile chemicals in various liquids and tissues. Toxicol Appl Pharmacol 98:87–99
Gassner B, Wuthrich A, Scholtysik G, Solioz M (1997) The pyrethroids permethrin and cyhalothrin are potent inhibitors of the mitochondrial complex I. J Pharmacol Exp Ther 281:855–860
GastroPlus Users Manual (2008) version 6.0, Simulations-Plus, Inc., Lancaster, CA
Gaughan LC, Unai T, Casida JE (1977) Permethrin metabolism in rats. J Agric Food Chem 25:9–17
Geinoz S, Guy RH, Testa B, Carrupt PA (2004) Quantitative structure-permeation relationships (QSPeRs) to predict skin permeation: a critical evaluation. Pharm Res 21:83–92
Ghiasuddin SM, Soderlund DM (1985) Pyrethroid insecticides potent, stereospecific enhancers of mouse brain sodium channel activation. Pestic Biochem Physiol 24:200–206
Girelli AM, Messina A, Sinibaldi M (2002) A study on the separation of synthetic pyrethroid stereoisomers by HPLC. Ann Chim 92:417–424
Glomot R (1979) RU 25474, active material: acute oral toxicity study in the rat. American Hoechst Corporation Study No. RU-4BE-79818-19/A.
Godin SJ, Scollon EJ, Hughes MF, Potter PM, DeVito MJ, Ross MK (2006) Species differences in the in vitro metabolism of deltamethrin and esfenvalerate: differential oxidative and hydrolytic metabolism by humans and rats. Drug Metab Dispos 34:1764–1771
Godin SJ, Crow JA, Scollon EJ, Hughes MF, DeVito MJ, Ross MK (2007) Identification of rat and human cytochrome P450 isoforms and a rat serum esterase that metabolize the pyrethroid insecticides Deltamethrin and Esfenvalerate. Drug Metab Dispos 35:1664–1671
Godin SJ, DeVito MJ, Hughes MF, Ross DG, Scollon EJ, Starr JM, Setzer RW, Conolly RB, Tornero-Velez R (2010) Physiologically based pharmacokinetic modeling of deltamethrin: development of a rat and human diffusion-limited model. Toxicol Sci 115:330–343
Goksu EI, Vanegas JM, Blanchette CD, Lin W-C, Longo ML (2009) AFM for structure and dynamics of biomembranes. Biochem Biophys Acta 1788:254–266
Goodman LS (2001) Goodman & Gilman’s the pharmacological basis of therapeutics, 10th edn. McGraw-Hill, New York
Gray AJ, Soderlund DM (1985) Mammalian toxicology of pyrethroids. In: Hutson DH, Roberts TR (eds) Insecticides. Wiley, New York, pp 193–248
Grosman N, Diel F (2005) Influence of pyrethroids and piperonyl butoxide on the Ca+2 –ATPase activity. Int J Immunopharmacol 5:263–270
Guengerich FP, Martin MV (1998) Purification of cytochromes P450. Rat and human hepatic forms. Methods Mol Biol 107:35–53
Guy RH, Hadgraft J, Bucks DA (1987) Transdermal drug delivery and cutaneous metabolism. Xenobiotica 17:325–343
Hagiwara N, Irisawa H, Kameyama M (1988) Contribution of two types of calcium currents to the pacemaker potentials of rabbit sino-atrial node cells. J Physiol 395:233–253
Hallifax D, Houston JB (2006) Binding of drugs to hepatic microsomes: comment and assessment of current prediction methodology with recommendation for improvement. Drug Metab Dispos 34:724–726
Hamman I, Fuchs R (1981) Baythroid®, a new insecticide. Pflanzenschutz-Nachrichten Bayer 34:121–151
Hansch C, Hoekman D, Leo A, Zhang L, Li P (1995) The expanding role of quantitative structure-activity relationships (QSAR) in toxicology. Toxicol Lett 79:45–43
Hardt J, Angerer J (2003) Biological monitoring of workers after the application of insecticidal pyrethroids. Int Arch Occup Environ Health 76:492–498
Harrison SM, Barry BW, Dugard PH (1984) Effects of freezing on human-skin permeability. J Pharm Pharmacol 36:261–262
Heimann KG (1987) FCR 1272 (c.n. cyfluthrin): Study for acute oral toxicity to rats (formulation acetone and peanut oil). Bayer Corporation Agricultural Division Report No. 106805.
Hemming H, Flodstrom S, Warngard L (1993) Enhancement of altered hepatic foci in rat-liver and inhibition of intercellular communication in-vitro by the pyrethroid insecticides fenvalerate, flucythrinate and cypermethrin. Carcinogenesis 14:2531–2535
Henrick CA (1977) Zoecon Corp. (patent for fluvalinate development).
Henrick CA, Garcia BA, Staal GB, Cerf DC, Anderson RJ, Gill K, Chinn HR, Labovitz JN, Leippe MM, Woo SL, Carney RL, Gordon DC, Kohn GK (1980) 2-Anilino-3-methylbutyrates and 2-(isoindolin-2-yl)-3-methylbutyrates, two novel groups of synthetic pyrethroid esters not containing a cyclopropane ring. Pestic Sci 11(2):224–241
Hildebrand ME, McRory JE, Snutch TP, Stea A (2004) Mammalian voltage-gated calcium channels are potently blocked by the pyrethroid insecticide allethrin. J Pharmacol Exp Ther 308:805–813
Hood SR, Shah G, Jones P (1998) Ch 24, Expression of cytochromes P450 in a Baculovirus system. In: Phillips IR, Shepard EA (eds) Methods in molecular biology: CYP protocols. Humana, Totowa, NJ, pp 203–218
Horber JKH, Mosbacher J, Haberle W, Ruppersberg JP, Sakmann B (1995) A look at membrane patches with a scanning force microscope. Biophys J 68:1687–1693
Hosokawa M, Maki T, Satoh T (1987) Muliplicity and regulation of hepatic microsomal carboxylesterases in rats. Mol Pharmacol 31:579–584
Hosokawa M, Maki T, Satoh T (1990) Characterization of molecular species of liver microsomal carboxylesterases of several animal species and humans. Arch Biophys 277:219–227
Hotchkiss SAM, Miller JM, Caldwell J (1992) Percutaneous absorption of benzyl acetate through rat skin in vitro. 2. Effect of vehicle and occlusion. Food Chem Toxicol 30:145–153
Houston JB (1994) Utility of in vitro drug metabolism data in predicting in vivo metabolic clearance. Biochem Pharmacol 47:1469–1479
Huang T, Kuang C, Zhou J, Gou D (1991) Chiral separation of water soluble. BETA-Lactam Enanatiomers on BETA-Cyclodextrin bonded stationary phase. Fenxi Huaxue 16:687–689
Huckle KR, Chipman JK, Hutson DH, Miliburn P (1981a) Metabolism of 3-phenoxybenzoic acid and the enterohepatorenal disposition of its metabolites in the rat. Drug Metab Dispos 9:360–368
Huckle KR, Hutson DH, Millburn P (1981b) Species differences in the metabolism of 3-phenoxybenzoic acid. Drug Metab Dispos 9:352–359
Huckle KR, Hutson DH, Millburn P (1984) Metabolism of 3-phenoxybenzoic acid in isolated rat hepatocytes and renal tubule fragments. Drug Metab Dispos 12:264–265
Huff RK (1978) Halogenated esters of cyclopropane acids, their preparation, composition and use as pesticides. Eur Pat 0010879 ICI.
Hutson DH, Logan CJ (1986) The metabolic fate in rats of the pyrethroid insecticide WL85871, a mixture of two isomers of cypermethrin. Pestic Sci 17:548–558
IARC (1991) Occupational exposures in insecticide application and some pesticides. IARC, Lyon
Inoue S, Howgate EM, Rowland-Yeo K, Shimada T, Yamazaki H, Tucker GT, Rostami-Hodjegan A (2006) Prediction of in vivo drug clearance from in vitro data. II: Potential inter-ethnic differences. Xenobiotica 36:499–513
Irvine JD, Takahashi L, Lockhart K, Cheong J, Tolan JW, Selick HE, Grove JR (1999) MDCK (Madin-Darby Canine Kidney) cells: a tool for membrane permeability screening. J Pharm Sci 88:28–33
Iwatsubo T, Hirota N, Ooie T, Suzuki H, Chiba K, Ishizaki T, Green CE, Tyson CA, Sugiyama Y (1997) Prediction of in vivo drug metabolism in the human liver from in vitro metabolism data. Pharmacol Ther 73:147–171
Izumi T, Kaneko H, Matsuo M, Miyamoto J (1984) Comparative metabolism of the six stereoisomers of phenothrin in rats and mice. J Pestic Sci 9:259–267
Jarabek A (2002) External Review Draft NCEA-1-0503, Office of Research and Development. US Environmental Protection Agency, Washington, DC
Jepson GW, Hoover DK, Black RK, McCafferty JD, Mahle DA, Gearhart JM (1992) Partition coefficient determination for nonvolatile and intermediate volatility chemicals in biological tissues. Toxicology 12:262
Jepson GW, Hoover DK, Black RK, McCafferty JD, Mahle DA, Gearhart JM (1994) A partition coefficient determination methods for non-volatile chemicals in biological issues. Fundam Appl Toxicol 22:519–524
Johnson PL (2007) Synthesis of (S)-cyano (3-phenoxyphenyl) methyl (1R, 3R)-3-[(1Z)-2-chloro-3, 3, 3-trifluoro-1-propenyl)-2, 2-dimethylcyclopropanecarboxylate-1-14C. J Label Compd Radiopharm 50:47–53
Jutsum AR, Gordon RF, Ruscoe CNE (1986) In: Proc. 1986 Brit Crop Prot Conf Pests and Diseases, BCPC, Croydon, pp 97–106.
Kakko I, Toimela T, Tahti H (2003) The synaptosomal membrane bound ATPase as a target for the neurotoxic effects of pyrethroids, permethrin and cypermethrin. Chemosphere 51:475–480
Kaneko H (2010) Chapter 76, Pyrethroid chemistry and metabolism. In: Krieger R (ed) Hayes’ handbook of pesticide toxicology, 3rd edn. Academic, San Diego, CA
Kaneko H, Miyamoto J (2001) Pyrethroid chemistry and metabolism, chapter 58. In: Krieger R (ed) Hayes handbook of pesticide toxicology, 2nd edn. Academic, San Diego, CA
Kaneko H, Ohkawa H, Miyamoto J (1981a) Adsorption and metabolism of dermally applied phenothrin in rats. Nippon Noyaku Gakkaishi 6:169–182
Kaneko H, Ohkawa H, Miyamoto J (1981b) Comparative metabolism of fenvalerate and the [2S, αS]-isomer in rats and mice. Nippon Noyaku Gakkaishi 6:317–326
Kaneko H, Ohkawa H, Miyamoto J (1981c) Metabolism of tetramethrin isomers in rats. Nippon Noyaku Gakkaishi 6:425–435
Kaneko H, Matsuo M, Miyamoto J (1984) Comparative metabolism of stereoisomers of cyphenothrin and phenothrin isomers in rats. Nippon Noyaku Gakkaishi 9:237–247
Kaneko H, Shiba K, Yoshitake A, Miyamoto J (1987) Metabolism of fenpropathrin (S-3206) in rats. Nippon Noyaku Gakkaishi 12:385–395
Kansy M, Senner F, Gubernator K (1998) Physicochemical high throughput screening: parallel artificial membrane permeation assay in the description of passive absorption processes. J Med Chem 41(7):1007–1010
Kato T, Ueda K, Fujimoto K (1965) New insecticidally active chrysanthemate. Agric Biol Chem 28:914–915
Katsuda Y (1975) Sumitomo Chemical Co, LTD. (patent for fluvalinate development).
Katsuda Y (1999) Development of and future prospects for pyrethroid chemistry. Pestic Sci 55:775–782
Khambay BPS (2002) Pyrethroid insecticides. Royal Society of Chemistry (UK). Pestic Outlook 49–54.
Killeen JCJ (1975) Acute oral toxicity study in rats with FMC 33297. FMC Corp, Philadelphia, PA
Klopman G, Rosenkranz HS (1995) Toxicity estimation by chemical substructure analysis: the TOX II program. Toxicol Lett 79:145–155
Knaak JB, Iwata Y, Maddy KT (1989) The worker hazard posed by reentry into pesticide-treated foliage: development of safe reentry times, with emphasis on chlorthiophos and carbosulfan, Ch 24. In: Paustenbach D (ed) The risk assessment of environmental hazards: a textbook of case studies. Wiley, New York, pp 797–842
Knaak JB, Wagner B, Boutchyard H Jr, Smith LW, Jones T, Wang RH (1993) Computerization of toxicological data by government agencies, chemical, and information industries, Ch 19. In: Jolley RL, Wang RGM (eds) Effective and safe waste management; interfacing sciences and engineering with monitoring and risk analysis. Lewis, Boca Raton, FL, pp 227–264
Knaak JB, Leung H-W, Stott WT, Busch J, Bilsky J (1997) Toxicology of mono-, di-, and triethanolamine. Rev Environ Contam Toxicol 149:1–86
Knaak JB, Dary C, Patterson GT, Blancato J (2002) The worker hazard posed by reentry into pesticide-treated foliage: reassessment of reentry levels/intervals using foliar residue transfer-percutaneous absorption PBPK/PD models, with emphasis on isofenphos and parathion. In: Paustenbach D (ed) Human and ecological risk assessment: theory and practice. Wiley, New York, pp 673–731
Knaak JB, Dary CC, Power F, Thompson CB, Blancato JN (2004) Physicochemical and biological data for the development of predictive organophosphorus pesticides QSARs and PBPK/PD models for human risk assessment. Crit Rev Toxicol 34:143–207
Knaak JB, Dary CC, Okino MS, Power FW, Zhang X, Thompson CB, Tornero-Velez R, Blancato JN (2008) Parameters for carbamate pesticide QSAR and PBPK/PD models for human risk assessment. Rev Environ Contam Toxicol 193:53–212
Kuo JK (1985) Phospholipids and cellular regulation. CRC, Boca Raton, FL
Kurihara N, Miyamoto J, Paulson GD, Zeeh B, Skidmore MW, Hollingsworth RM, Kuiper HA (1997a) Chirality in synthetic agrochemicals: bioactivity and safety considerations. Pure Appl Chem 69:1335–1348
Kurihara N, Miyamoto J, Paulson GD, Zeeh B, Skidmore MW, Hollingsworth RM, Kipper HA (1997b) Chirality in synthetic agrochemicals: bioactivity and safety consideration. Pure Appl Chem 69:2007–2026
Kutter JP, Class TJ (1992) Diastereoselective and enantioselective chromatography of the pyrethroid insecticides allethrin and cypermethrin. Chromatograhia 33:103–112
LaForge FB, Haller HL (1936) Constituents of pyrethrum flowers. VI. The structure of pyrethrolone. J Am Chem Soc 58:1777–1780
LaForge FB, Soloway SB (1947) Structure of dihydrocinerolone. J Am Chem Soc 69:186
Lau YY, Wu C-Y, Okochi H, Benet LZ (2003) Ex situ inhibition of hepatic uptake and efflux significantly changes metabolism: hepatic enzyme-transporter interplay. J Pharmacol Exp Ther 308:1040–1045
Lawrence LJ, Gee KW, Yamamura HI (1985) Interactions of pyrethroid insecticides with chloride ionophore-associated binding sites. Neurotoxicology 6:87–98
Lee W, Kim B-H (1998) Liquid chromatographic resolution of pyrethroic acids and their esters on chiral stationary phases. J High Resol Chromatogr 21:189–192
Leng G, Leng A, Kuhn K-H, Lewalter J, Pauluhn J (1997) Human dose-excretion studies with the pyrethroid insecticide cyfluthrin: urinary metabolite profile following inhalation. Xenobiotica 27:1273–1293
Li Z-Y, Zhang Z-C, Zhou Q-L, Wang Q-M, Gao R-Y, Wang Q-S (2003) Stereo and enantioselective determination of pesticides in soil by using achiral and chiral liquid chromatography in combination with matrix solid-phase dispersion. J AOAC Int 86(3):521–528
Li Z-Y, Zhang Z-C, Zhang L, Leng L (2006) Chiral separation of pyrethroids pesticides and fenvaleric acid. Fenxi Shiyanshi (Chin J Anal Lab) 25(11):11–14
Li Z, Zhang Z, Zhang L, Leng L (2009) Isomer- and enantioselective degradation and chiral stability of fenpropathrin and fenvalerate in soils. Chemosphere 76:509–516
Liang R, Fei Y-J, Prasad PD, Ramamoorthy S, Han H, Yang-Feng TL, Hediger MA, Ganapathy V, Leibach FH (1995) Human intestinal H+/peptide cotransporter: cloning, functional expression, and chromosomal localization. J Biol Chem 270:6456–6463
Lin JH, Yamazaki M (2003) Role of P-glycoprotein in pharmacokinetics: clinical implications. Clin Pharmacokinet 42:59–98
Lipscomb JC, Fisher JW, Confer PD, Byczkowski JZ (1998) In vitro to in vivo extrapolation for trichloroethylene metabolism in humans. Toxicol Appl Pharmacol 152:376–387
Liu HX, Yao XJ, Zhang RS, Liu MC, Hu ZD, Fan BT (2005a) Prediction of the tissue/blood partition coefficients of organic compounds based on the molecular structure using least-squares support vector machines. J Comput Aided Mol Des 19:499–508
Liu W, Gan J, Schlenk D, Jury WA (2005b) Enantioselectivity in environmental safety of current chiral insecticides. Proc Natl Acad Sci USA 102(3):701–706
Liu W, Gan JJ, Qin S (2005c) Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides. Chirality 17:S127–S133
Liu W, Gan J, Lee S, Werner I (2005d) Isomer selectivity in aquatic toxicity and biodegradation of bifenthrin and permethrin. Environ Toxicol Chem 24(8):1861–1866
Lu AYH, West SB (1980) Multiplicity of mammalian microsomal cytochrome P450. Pharmacol Rev 31:277–291
Maibach HI, Feldmann RJ, Milby TH, Serat WF (1971) Regional variation in percutaneous penetration in man. Arch Environ Health 23:208–211
Mancini F, Fiori J, Bertucci C, Cavrini V, Bragieri M, Zanotti MC, Liverani A, Borzatta V, Andrisano V (2004) Stereoselective determination of allethrin by two-dimensional achiral/chiral liquid chromatography with ultraviolet/circular dichroism detection. J Chromatogr A 1046:67–73
Martel J (1976) Roussel UCLAF (patent, tralomethrin development).
Matsuo T, Itaya N, Mizutani T, Ohno N, Fujimoto K, Okuno Y, Yoshioka H (1976) 3-phenoxy-a-cyanobenzyl esters, the most potent synthetic pyrethroids. Agric Biol Chem 40:247–249
Mattie DR, Bates GD, Jepson GW, Fisher JW, McDougal JN (1994) Determination of skin: air partition coefficients for volatile chemicals: experimental method and applications. Toxicol Appl Pharmacol 22:51–57
McGregor DB (1999) Permethrin Joint Meeting, FAO Panel of Experts on Pesticide Residues in Food and the Environment, and WHO Core Assessment Group, Rome.
Meylan WM, Howard PH (1994a) Upgrade of PCGEMS water solubility estimation method (draft). US Environmental Protection Agency, Office of Pollution Prevention and Toxics, Washington, DC
Meylan WM, Howard PH (1994b) Validation of water solubility estimation methods using log Kow for application in PCGEMS & EPI. Final report, U.S. Environmental Protection Agency, Office of Pollution Prevention and Toxics, Washington, DC.
Mirfazaelian A, Kim K-B, Anand SS, Kim HJ, Tornero-Velez R, Bruckner JV, Fisher JW (2006) Development of a physiologically based pharmacokinetic model for deltamethrin in the adult male Sprague-Dawley rat. Toxicol Sci 93:432–442
Miyamoto J (1976) Degradation, metabolism and toxicity of synthetic pyrethroids. Environ Health Perspect 14:15–28
Miyamoto J, Nishida T, Ueda K (1971) Metabolic fate of resmethrin, 5-benzyl-3-furylmethyl dl-trans chrysanthemate in the rat. Pestic Biochem Physiol 1:293–306
Miyamoto J, Suzuki T, Nakae C (1974) Metabolism of phenothrin (3-phenoxybenzyl d-trans-chrysanthemumate) in mammals. Pestic Biochem Physiol 4:438–450
Moss GP, Derden JC, Patel H, Cronin MT (2002) Quantitative structure-permeability relationships (QSPRs) for percutaneous absorption. Toxicol In Vitro 16:299–317
Mugeng J, Soderlund DM (1982) Liquid chromatographic determination and resolution of the enantiomers of the acid moieties of pyrethroid insecticides as their (-)-1-(1-phenyl)ethylamide derivatives. J Chromatogr A 248(1):143–149
Myer JR (1989) Acute oral toxicity study of deltamethrin in rats. Hoechst-Roussel Agri-Vet Company Study No. 327-122.
Nakamura Y, Sugihara K, Sone T, Isobe M, Ohta S, Kitamura S (2007) The in vitro metabolism of a pyrethroid insecticide, permethrin, and its hydrolysis products in rats. Toxicology 235:176–184
Narahashi T (1971) Mode of action of pyrethroids. Bull World Health Organ 44:337–345
Nardini M, Dijkstra BW (1999) α/β Hydrolase fold enzymes: the family keeps growing. Curr Opin Struct Biol 9:732–737
Naumann K (1998) Research into fluorinated pyrethroid alcohols-an episode in the history of pyrethroid discovery. Pestic Sci 52:3–20
Nicoli S, Santi P (2007) Suitability of excised rabbit ear skin – fresh and frozen – for evaluation Transdermal permeation of estradiol. Drug Deliv 14:195–199
Nigg HN, Knaak JB (2000) Blood cholinesterases as human biomarkers of organophosphorus pesticide exposure. Rev Environ Contam Toxicol 163:29–112
Nikolelis DP, Brennan JD, Brown S, McGibbon G, Krull UJ (1991) Ion permeability through bilayer lipid membranes for biosensor development: control by chemical modification of interfacial regions between phase domains. Analyst 116:1221–1226
Nishizawa Y (1971) Development of new synthetic pyrethroids. Bull World Health Organ 44:325–336
Nong A, Tan Y-M, Krolski ME, Wang J, Lunchick C, Conolly RB, Clewell HJ III (2008) Bayesian calibration of a physiologically-based pharmacokinetic/pharmacodynamic model of carbaryl cholinesterase inhibition. J Toxicol Environ Health A 71:1363–1381
O’Reilly AO, Khanbay BPS, Williamson MS, Field LM, Wallace BS, Davies TGE (2006) Modeling insecticide-binding sites in the voltage-gated sodium channel. Biochem J 396:255–263
Obach RS (1996) The importance of nonspecific binding in in vitro matrices, its impact on enzyme kinetic studies of drug metabolism and implications for in vitro-in vivo correlations. Drug Metab Dispos 24:1047–1049
Obach RS (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 RS (1999) The prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: an examination of the in vitro half-life approach and non-specific binding to microsomes. Drug Metab Dispos 27:1350–1359
Ohkawa H, Kaneko H, Tsuji H, Miyamoto J (1979) Metabolism of fenvalerate (Sumicidin) in rats. J Pestic Sci (J Nippon Noyaku Gakkaishi) 4:143–155
Ohno N, Fujimoto K, Okuno Y, Mizutani T, Hirano M, Yoshioka H (1974) A new class of pyrethroidal insecticides: α-substituted phenylacetic acid esters. Agric Biol Chem 38:881–883
Oi N (2005) Development of practical chiral stationary phases for chromatography and their applications. Chromatography 26(1):1–5
Oi N, Horiba M, Kitahara H (1981) Gas chromatographic separation of optical isomers of chrysanthemic acid on an optically active stationary phase. Agric Biol Chem 45(6):1509–1510
Oi N, Kitahara H, Kira R (1990) Enantiomer separation of pyrethroid insecticides by high-performance liquid chromatography with chiral stationary phases. J Chromatogr A 515:441–450
Oi N, Kitahara H, Aoki F, Kisu N (1995) Direct separation of carboxylic acid enantiomers by high-performance liquid chromatography with amide and urea derivatives bonded to silica gel as chiral stationary phases. J Chromatogr A 689(2):195–201
Oi N, Kitahara H, Matsushita Y, Kisu N (1996) Enantiomer separation by gas and high-performance liquid chromatography with tripeptide derivatives as chiral stationary phases. J Chromatogr A 722(1–2):229–232
Omura T, Sato (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370–2378
Paine MF, Khalighi M, Fisher JM, Shen DD, Kunze KOL, Cl M, Perkins JD, Thummel KE (1997) Characterization of interintestinal and intraintestinal variations in human CYP3A-dependent metabolism. J Pharmacol Exp Ther 283:1552–1562
Papadopoulou-Mourkidou E (1985) Direct analysis of fenvalerate isomers by liquid chromatography. Application to formulation and residue analysis of fenvalerate. Chromatographia 20(6):376–378
Payne MP, Kenny LC (2002) Comparison of models for the estimation of biological partition coefficients. J Toxicol Environ Health A 65:897–931
PMRA (Canada Pest Management Regulatory Agency) (2005) Report PRDD#2005-02 (imiprothrin), www.pmra-arla.gc.ca/english/pdf/prdd/prdd2005-02-e.pdf, Aug 8 2005.
Plummer EL, Cardis AB, Martinez AJ, Van Saun WA, Palmere RM, Pincus DS, Stewart RR (1983) Pyrethroid insecticides derived from substituted biphenyl-3-methods. Pestic Sci 14:560–570
Porcelli C, Roncaglioni A, Chana A, Boriani E, Benfenati A (2007) A protocol for quantitative structure, activity relationship (QSAR) for regulatory purposes: the example of DEMETRA. In Environmental fate and ecological effects of pesticides, symposium pesticide chemistry, 13th, Placenza, Italy, Sept. 3–6, 2007, pp 669–674.
Potts RO, Guy RH (1992) Predicting skin permeability. Pharm Res 9:663–669
Potts RO, Guy RH (1995) A predictive algorithm for skin permeability: the effects of molecular size and hydrogen bond activity. Pharm Res 12:1628–1633
Poulin P, Theil F-P (2000) A priori prediction of tissue: plasma partition coefficients of drugs to facilitate the use of physiologically-based pharmacokinetic models in drug discovery. J Pharm Sci 89:16–35
Poulin P, Theil F-P (2002a) Prediction of pharmacokinetics prior to in vivo studies. I. Mechanism-based prediction of volume of distribution. J Pharm Sci 91:129–156
Poulin P, Theil F-P (2002b) Prediction of pharmacokinetics prior to in vivo studies. II. Generic physiologically-based pharmacokinetic models of drug disposition. J Pharm Sci 91:1358–1370
Prout M, Howard E (1985b) PP993: excretion and tissue distribution of a single oral dose (10 mg/kg) in the rat. Syngenta unpublished report, no. CTL/P/1256, UK.
Prout M, Howard E, Soames A (1985a) PP993: Absorption, excretion and tissue distribution of a single oral dose (1 mg/kg) in the rat. Syngenta unpublished report, no. CTL/P/1064, UK.
Prout M, Gibson N, Howard E (1986) PP993: Biotransformation in the rat. Syngenta unpublished report, no. CTL/P/1295, UK.
Casida JE (ed) (1973) Pyrethrum: the natural insecticide. Academic, New York
Quistad GB, Staiger LE, Jamieson GC, Schooley DA (1983) Fluvalinate metabolism by rats. J Agric Food Chem 31:589–596
Rand G (1983) Acute oral toxicity-cypermethrin technical. FMC Corporation Study No. A82-727.
Rao RN, Shankaraiah B, Sunder MS (2004) Separation and determination of diastereomers of γ-Cyhalothrin by normal phase-liquid chromatography using a CN column. Anal Sci 20:1745–1748
Ray DE, Fry JR (2006) A reassessment of the neurotoxicity of pyrethroids insecticides. Pharmacol Ther 111:174–193
Ray DE, Sutharsan S, Forshaw PJ (1997) Actions of pyrethroid insecticides on voltage-gated chloride channels in neuroblastoma cells. Neurotoxicology 18:755–760
Reifenrath WG, Kamppainen BW (1991) Skin storage conditions. In: Bronaugh R, Maibach H (eds) In vitro percutaneous absorption: principles, fundamentals and applications. CRC, Boca Raton, pp 115–125
Reifenrath WG, Ross JH, Driver JH (2011) Experimental methods for determining permethrin dermal absorption. Submitted for review and publication. J Toxicol Environ Health A 74: 325–335.
Rekling JC, Theophilidis GN (1995) Effects of the pyrethroid insecticide, deltamethrin, on respiratory modulated hypoglossal moto-neurons in a brain stem slice from newborn mice. Neurosci Lett 198:189–192
Riddles PW, Richards LJ, Bowles MR, Pond SM (1991) Cloning and analysis of a cDNA encoding a human liver carboxylesterase. Gene (Amst) 108:389–392
Riviere JE, Monteiro-Riviere NA (1991) The isolated perfused porcine skin flap as an in vitro model for percutaneous absorption and cutaneous toxicology. Crit Rev Toxicol 21:329–344
Riviere JE, Bowman KF, Monteiro-Riviere NA, Dix LP, Carver MP (1986) The isolated perfused porcine skin flap (IPPSF). I. A novel in vitro model for percutaneous absorption and cutaneous toxicology studies. Fund Appl Toxicol 7:444–453
Robey RW, Lin B, Qui J, Chan LL, Bates SE (2010) Rapid detection of ABC transporter interaction: potential utility in pharmacology. J Pharmacol Toxicol Methods 63:217–222
Rodgers T, Rowland M (2006) Physiologically based pharmacokinetic modelling 2: predicting the tissue distribution of acids, very weak bases, neutral and zwitterions. J Pharm Sci 95:1238–1257
Rodgers T, Rowland M (2007) Mechanistic approaches to volume of distribution predictions: understanding the processes. Pharm Res 24:918–933
Rodgers T, Leahy D, Rowland M (2005) Physiologically based pharmacokinetic modeling 1: predicting the tissue distribution of moderate-to-strong bases. J Pharm Sci 94:1259–1276
Rodgers T, Leahy D, Rowland M (2007) (ERRATA) Physiologically based pharmacokinetic modeling 1: predicting the tissue distribution of moderate to strong bases. J Pharm Sci 96:1259–1276, J Pharm Sci 96: 3151–3152
Rodrigues AD (1999) Integrated cytochrome P450 reaction phenotyping: attempting to bridge the gap between cDNA-expressed cytochrome P450 and native human liver microsomes. Biochem Pharmacol 57:465–480
Ross MK, Borazjani A, Edwards CC, Potter PM (2006) Hydrolytic metabolism of pyrethroids by human and other mammalian carboxylesterases. Biochem Pharmacol 71:657–669
Ruzo LO, Casida JE (1977) Metabolism and toxicology of pyrethroids with dihalovinyl substituents. Environ Health Perspect 21:285–292
Ruzo LO, Casida JE (1981) Pyrethroid photochemistry: (S)-a-cyano-3-phenoxybenzyl cis-(1R,3R,1′R or S)-3-(1′,2′-dibromo-2′,2′-dihaloethyl)-2,2-dimethylcyclopropanecarboxylates. J Agric Food Chem 29:702–706
Ruzo LO, Unai T, Casida JE (1978) Decamethrin metabolism in rats. J Agric Food Chem 26:918–925
Ruzo LO, Engel JL, Casida JE (1979) Decamethrin metabolites from oxidative, hydrolytic, and conjugative reactions in mice. J Agric Food Chem 27:725–731
Saiakhov RD, Stefan LR, Klopman G (2000) Multiple computer-automated structure evaluation model of the plasma protein binding affinity of diverse drugs. Perspect Drug Discov Des 19:133–155
Sanchez FG, Diaz AN, Pareja AG (1996) Enantiomeric resolution of pyrethroids by high-performance liquid chromatography with diode-laser polarimetric detection. J Chromatogr A 754:97–102
Satoh T, Hosokawa M (1998) The mammalian carboxylesterases: from molecules to functions. Annu Rev Pharmacol Toxicol 38:257–288
Satoh T, Hosokawa M (2010) Carboxylesterases: structure, function and polymorphism in mammals. J Pestic Sci 35:218–228
Scheuplein RJ, Blank IH (1971) Permeability of the skin. Physiol Rev 51:702–747
Schwenkenbecker A (1904) Das absorptions verniogen der haut. Arch Anat Physiol 121–165.
Schwer H, Langmann T, Daig R, Becker A, Aslanidis C, Schmitz G (1997) Molecular cloning and characterization of a novel putative carboxylesterase, present in human intestine and liver. Biochem Biophys Res Commun 233:117–120
Scollon EJ, Starr JM, Godin SJ, DeVitro MJ, Hughes MF (2009) In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome P450 isoforms. DMD 37:221–228
Scott RC, Ramsay JD (1987) Comparison of the in vivo and in vitro percutaneous absorption of a lipophilic molecule (cypermethrin, a pyrethroid insecticide). J Invest Dermatol 89:142–146
Serat WF (1973) Calculation of a safe reentry time into an orchard treated with a pesticide chemical which produces a measurable physiological response. Arch Environ Contam Toxicol 1:170–181
Serat WF, Bailey JB (1974) Estimating the relative toxicologic potential of each pesticide in mixture of residues on foliage. Bull Environ Contam Toxicol 12:682–686
Serat WF, Mengle DC, Anderson HP, Kahn E (1975) On the estimation of worker entry intervals into pesticide treated fields with and without the exposure of human subjects. Bull Environ Contam Toxicol 13:506–512
Shafer TJ, Meyer DA, Crofton KM (2005) Developmental neurotoxicity of pyrethroid insecticides: critical review and future research needs. Environ Health Perspect 113:123–135
Sidon EW, Moody RP, Franklin CA (1988) Percutaneous absorption of cis- and trans-permethrin in rhesus monkeys and rats: Anatomic site and interspecies variation. J Toxicol Environ Health A 23:207–216
Smith PA, Thompson MJ, Edwards JW (2002) Estimating occupational exposure to the pyrethroid termiticide bifenthrin by measuring metabolites in urine. J Chromatogr B 778:113–120
Soderlund DM, Clark JM, Sheets LP, Mullin LS, Piccirillo VJ, Sargent D, Stevens JT, Weiner ML (2002) Mechanisms of pyrethroid neurotoxicity: implications for cumulative risk assessment. Toxicology 171:3–59
Song J-H, Narahashi T (1996) Modulation of sodium channels of rat cerebellar Purkinje neurons by the pyrethroid tetramethrin. J Pharmacol Exp Ther 277:445–453
Sorich MJ, McKinnon RA, Miners JO, Smith PA (2006) The importance of local chemical structure for chemical metabolism by human uridine 5′-diphosphate-gluronyltransferase. J Chem Inf Model 46:2692–2697
Southwood J (1985a) PP321: Acute oral toxicity studies. Zeneca Agricultural Products Laboratory Project No. CTL/P/1102, Wilmington, DE.
Southwood J (1985b) PP993: Acute oral toxicity, acute intraperitoneal toxicity, and acute dermal toxicity studies. Zeneca Agricultural Products Laboratory Project No. CTL/P/986, Wilmington, DE.
Staiger LE, Quistad GB (1984) Metabolism of [benzyl-U-ring-14C] fluvalinate by rats. J Agric Food Chem 32:1130–1133
Stephens RH, O’Neill CA, Warhurst A, Carlson GL, Rowland M, Warhurst G (2001) Kinetic profiling of P-glycoprotein-mediated drug efflux in rat and human intestinal epithelia. J Pharmacol Exp Ther 296:584–591
Stok JE, Huang H, Jones PD, Wheelock CE, Morisseau C, Hammock BD (2004) Identification, expression, and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes. J Biol Chem 279:29863–29869
Sudhahar CG, Haney RM, Xue Y, Stahelin RV (2008) Cellular membranes and lipid-binding domains as attractive targets for drug development. Curr Drug Targets 9:603–613
Suzuki T, Miyamoto J (1974) Metabolism of tetramethrin in houseflies and rats in vitro. Pestic Biochem Physiol 4:86–97
Suzuki T, Ohno N, Miyamoto J (1976) New metabolites of (+)-cis-fenothrin, 3 phenoxybenzyl (+)-cis-chrysanthemumate, in rats. J Pestic Sci 1:151–152
Symington SB, Frisbie RK, Clark JM (2008) Characterization of 11 commercial pyrethroids on the functional attributes of rat brain synaptosomes. Pestic Biochem Physiol 92:61–69
Tamai I, Takanaga H, Maeda H, Sai Y, Ogihara T, Higashida H, Tsuji A (1995) Participation of a proton-cotransporter, MCT1, in the intestinal transport of monocarboxylic acid. Biochem Biophys Res Commun 214:482–489
Tan HL, Bezzina CR, Smits JPP, Verkerk AO, Wilde AAM (2003) Genetic control of sodium channel function. Cardiovasc Res 57:961–973
Tan J, Liu Z, Wang R, Huang ZY, Chen AC, Gurevitz M, Dong K (2005) Identification of amino acid residues in the insect sodium channel critical for pyrethroid binding. Mol Pharmacol 67:513–522
Tan X, Hou S, Wang M (2007) Enantioselective and diastereoselective separation of synthetic pyrethroid insecticides on a novel chiral stationary phase by high-performance liquid chromatography. Chirality 19:574–580
Tatebayashi H, Narahashi T (1994) Differential mechanism of action of the pyrethroid tetramethrin on tetrodotoxin-sensitive and tetrodotoxin-resistant sodium channels. J Pharmacol Exp Ther 270:595–603
Tateno C, Ito S, Tanaka M, Yoshitake A (1993) Effects of pyrethroid insecticides on gap junctional intercellular communications in Balb/c3T3 cells by dye-transfer assay. Cell Biol Toxicol 9:215–221
Timchalk C, Nolan RJ, Mendrala AL, Dittenber DA, Brzak KA, Mattsson JL (2002) A physiologically-based pharmacokinetic and pharmacodynamic (PBPK/PD) model for the organophosphate insecticide chlorpyrifos in rats and humans. Toxicol Sci 66:34–53
Tomigahara Y, Mori M, Shiba K, Isobe N, Kaneko H, Nakatsuka I, Yamada H (1994a) Metabolism of tetramethrin isomers in rat. I. Identification of a sulfonic acid type of conjugate and reduced metabolites. Xenobiotica 24:473–484
Tomigahara Y, Mori M, Shiba K, Isobe N, Kaneko H, Nakatsuka I, Yamada H (1994b) Metabolism of tetramethrin isomers in rat. II. Identification and quantification of metabolites. Xenobiotica 24:1205–1214
Tomigahara Y, Shiba K, Isobe N, Kaneko H, Nakatsuke I, Yamada H (1994c) Identification of two new types of S-linked conjugates of Etoc in rat. Xenobiotica 24:839–852
Tomigahara Y, Onogi M, Miki M, Yanagi K, Shiba K, Kaneko H, Nakatsuka I, Yamada H (1996) Metabolism of tetramethrin isomers in rat. III. Stereochemistry of reduced metabolites. Xenobiotica 26:201–210
Tomigahara Y, Onogi M, Saito K, Kaneko H, Nakatsuka I, Yamane S (1997) Metabolism of tetramethrin in rat. IV. Tissues responsible for formation of reduced and hydrated metabolites. Xenobiotica 27(9):961–971
Tornero-Velez R, Mirfazaelian A, Kim KB, Anand SS, Kim HJ, Haines WT, Bruckner JV, Fisher JW (2010) Evaluation of deltamethrin kinetics and dosimetry in the maturing rat using PBPK model. Toxicol Appl Pharmacol 244:208–217
Tsuji T, Kaneda N, Kado K, Yokokura T, Yoshimoto T, Tsuru D (1991) CPT-11 converting enzyme from rat serum: purification and some properties. J Pharmacobiodyn 14:341–349
Tubic M, Wagner D, Spahn-Langguth H, Bolger MB, Langguth P (2006) In silico modeling of non-linear drug absorption for the P-gp substrate Talinolol and of consequences for the resulting pharmacodynamic effect. Pharm Res 23:1712–1720
Tullman RH (1987) Data Evaluation Report No. 005731. U.S. Environmental Protection Agency, Washington, DC
Ueda K, Gaughan LC, Casida JE (1975) Metabolism of (+)-trans- and (+)-cis -Resmethrin in rats. J Agric Food Chem 23:106–115
Ueda K, Cornwell MM, Gottesman MM, Pastan I, Roninson IB, Ling V, Riordan JR (1986) The mdr1 gene, responsible for multidrug-resistance, codes for P-glycoprotein. Biochem Biophys Res Commun 141:956–962
Ulrich E, Sey YM, Harrison RA, DeVito MJ (2008) LC/MS method for the analysis of permethrin enantiomers in biological matrices. 20th International Symposium on Chirality, Geneva, Switzerland, July 6–9, 2008.
Unai T, Casida JE (1977) Synthesis of isomeric 3-(2,2-Dichlorovinyl)-2-hydroxymethyl-2-methylcyclopropanecarboxylic acids and other permethrin metabolites. J Agric Food Chem 25:979–987
Valverde A, Aguilera A, Rodriguez M, Boulaid M (2001) What are we determining using gas chromatographic multiresidue methods: tralomethrin or deltamethrin? J Chromatogr A 943(1):101–111
Van der Rhee HJ, Farquhar JA, Vermeulen NP (1989) Efficacy and transdermal absorption of permethrin in scabies patients. Acta Derm Venerol 69:170–173
Varsho BJ (1996) Acute oral toxicity study of deltamethrin in albino rats. AgrEvo USA Company Study No. WIL-274001.
Venkatakrishnan K, Von Moltke LL, Obach RS, Greenblatt DJ (2000) Microsomal binding of amitriptyline: effect on estimation of enzyme kinetic parameters in vitro. J Pharmacol Exp Ther 293:343–350
Vistoli G, Pedretti A, Mazzolari A, Testa B (2010) In silico prediction of human carboxylesterase-1 (hCES1) metabolism combining docking analysis and MD simulations. Bioorg Med Chem 18:320–329
Vozeh S, Taeschner W, Wenk M (1990) Pharmacokinetic drug data. In: Clinical pharmacokinetics drug data handbook. ADIS, Auckland, NZ. pp 1–38.
Wadkins RM, Hyatt JL, Wei X, Yoon KJP, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM (2005) Identification and characterization of novel benzyl (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem 48:2906–2915
Wang P, Zhou Z, Jiang S, Yang L (2004) Chiral resolution of cypermethrin on cellulose-tris(3,5-dimethylphenyl-carbamate) chiral stationary phase. Chromatographia 59:625–629
Wang Q, Qiu J, Zhu W, Jia G, Li J, Bi C, Zhou Z (2006) Stereoselective degradation kinetics of theta-cypermethrin in rats. Environ Sci Technol 40:721–726
Wang M, Wang Q, Hong C, Sleczka B, D’Arienzo C, Josephs J, Ye X-Y, Robl J, Gordon D, Rodrigues D, Harper T (2010) Prediction of in vivo enantiomeric compositions by modeling in vitro metabolic profiles. J Pharm Sci 99:3234–3245
Waxman SG, Craner MJ, Black JA (2004) Na+ channel expression along axons in multiple sclerosis and its models. Trends Pharmacol Sci 25:584–591
Weiner ML, Nemec M, Sheets L, Sargent D, Breckenridge (2009) Comparative functional observational battery study of twelve commercial pyrethroid insecticides in male rate following oral exposure. Neurotoxicology 30S:S1–S16
Wester RC, Maibach HI (1977) In: Drill VA, Lazar P (eds) Cutaneous toxicology. Academic, New York, p 111
Wester RC, Maibach HI (1993) Animal models for percutaneous absorption. In: Wang RGM, Knaak JB, Maibach HI (eds) Health risk assessment: dermal and inhalation exposure and absorption of toxicants. CRC, Boca Raton, FL
Wester RC, Noonan PK (1980) Relevance of animal-moles for percutaneous-absorption. Int J Pharm 7:99–110
Wester RC, Bucks DAW, Maibach HI (1994) Human in vivo percutaneous absorption of pyrethrin and piperonyl butoxide. Food Chem Toxicol 32:51–53
Wheelock CE, Wheelock AM, Zhang R, Stok JE, Morisseau C, Le Valley SE (2003) Evaluation of alpha-cyanoesters as fluorescent substrates for examining interindividual variation in general and pyrethroid-selective esterases in human liver microsomes. Anal Biochem 315:208–222
Wheelock CR, Miller JL, Miller MJ, Phillips BM, Huntley SA, Gee SJ, Tjeerdem RS, Hammock BD (2006) Use of carboxylesterase activity to remove pyrethroid-associated toxicity to Ceriodaphnia dubia and Hyalella azteca toxicity in identification evaluations. Environ Toxicol Chem 25:973–984
White S (1994) Protein membrane structure. Oxford University Press, Oxford
White INH, Verschoyle RD, Moradian MH, Barnes JM (1976) The relationship between brain levels of cismethrin and bioresmethrin in female rats and neurotoxic effects. Pestic Biochem Physiol 6:491–500
WHO (2005a) WHO Specifications and evaluations for public health pesticides, Deltamethrin, (S)-a-cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane carboxylate. WHO, Genève.
WHO (2005b) The WHO Recommended Classification of Pesticides by Hazard. Guidelines to Classification 2004, International Programme on Chemical Safety. WHO/PCS/01.5, Genève, http://www.who.int/ipcs/publications/pesticides_hazard/en/.
WHO (World Health Organization) (1965) Evaluation of the toxicity of pesticide residues in food: dimethrin. FAO meeting report PL/1965/10/1. Food and Agriculture Organization (United Nations) www.inchem.org/documents/jmpr/jmpmono/v065pr21.htm
Williams RL, Bernard CE, Krieger RI (2003) Human exposure to indoor residential cyfluthrin residues during a structured activity program. J Expo Anal Environ Epidemiol 13:112–119
Wilson ZE, Rostami-Hodjegan A, Burn JL, Tooley A, Boyle J, Ellis SW, Tucker GT (2003) Inter-individual variability in levels of human microsomal protein and hepatocellularity per gram of liver. Br J Clin Pharmacol 56:433–440
Wolansky MJ, Harrill JA (2008) Neurobehavioral toxicology of pyrethroid insecticides in adult animals: a critical review. Neurotoxicol Teratol 30:55–78
Woollen BH, Marsh JR, Laird WJD, Lesser JE (1992) The metabolism of cypermethrin in man: differences in urinary profiles following oral and dermal administration. Xenobiotica 22:983–991
Wu A, Liu Y (2003) Prolonged expression of c-Fos and c-Jun in the cerebral cortex of rats after deltamethrin treatment. Brain Res Mol Brain Res 110:147–151
Xu C, Wang J, Liu W, Sheng GD, Tu Y, Ma Y (2007) Separation and aquatic toxicity of enantiomers of the pyrethroid insecticide Lambda-Cyhalothrin. Environ Toxicol Chem 27:174–181
Yamamoto I, Elliot M, Casida JE (1971) Metabolic fate of pyrethrin I, pyrethrin II, and allethrin. Bull World Health Organ 44:347–348
Yamazaki K, Kanaoka M (2004) Computational prediction of the plasma protein-binding percent of diverse pharmaceutical compounds. J Pharm Sci 93:1480–1494
Yang J, Tucker GT, Rostami-Hodjegan A (2004a) Cytochrome P450 3A expression and activity in the human small intestine. Clin Pharmacol Ther 76:931
Yang G-S, Vazquez PP, Frenich AG, Vidal JLM, Aboul-Enein HY (2004b) Separation on CHIRALCEL OD-R with methanol/water, and acetonitrile/water mobile phases. J Liq Chromatogr Rel Technol 27(10):1507–1521
Yoon KJ-P, Krull EJ, Morton CL, Bornmann WG, Lee RE, Potter PM, Danks MK (2003) Activation of a camptothecin prodrug by specific carboxylesterases as predicted by quantitative structure-activity relationship and molecular docking studies. Mol Cancer Ther 2:1171–1181
Youdim K, Dodia R (2010) Comparison between recombinant P450s and human liver microsomes in the determination of cytochrome P450 Michaelis–Menten constants. Xenobiotica 40:235–244
Youdim KA, Zayed A, Dickins M, Phipps A, Griffiths M, Darekar A, Hyland R, Fahmi O, Hurst S, Plowchalk DR, Cook J, Guo F, Obach RS (2008) Application of CYP3a4 in vitro data to predict clinical drug-drug interactions: predictions of compounds as objects of interaction. Br J Clin Pharmacol 65:680–692
Yu LX, Lipka E, Crison JR, Amidon GL (1996) Transport approaches to the biopharmaceutical design of oral drug delivery systems: prediction of intestinal absorption. Adv Drug Del Rev 19:359–376
Zeng S, Tang Y (2009) Effect of clustered ion channels along an unmyelinated axon. Physical Rev E 80:1–9
Zhang H (2005) A new approach for the tissue-blood partition coefficients of neutral and ionized compounds. J Chem Inf Model 45:121–127
Zhang X, Tsang AM, Okino MS, Power FW, Knaak JB, Harrison LS, Dary CC (2007) A physiologically-based pharmacokinetic/pharmacodynamic (PBPK/PD) model for carbofuran in Sprague-Dawley rats using the Exposure Related Dose Estimating Model (ERDEM). Toxicol Sci 100:345–359
Zhe X, Wenwei X, Hua H, Lirui P, Xu X (2008) Direct chiral resolution and its application to the determination of the pesticide tetramethrin in soil by high-performance liquid chromatography using polysaccharide-type chiral stationary phase. J Chromatogr Sci 46:783–786
Acknowledgments
Our thanks are extended to Prof. Herbert N. Nigg, University of Florida, and Prof. James R. Olson, The State University of New York at Buffalo, for reviewing the manuscript of this article and making helpful suggestions that improve its quality. We also thank SRA International, Las Vegas, NV, for their skilled work in preparing this manuscript for publication and Dr. Robert Fraczkiewic, Simulations-plus, Lancaster, California, for calculating the Predicted V max and K m values for the CYP450s using ADMET Predictor.
The work on this review was funded by the US EPA through General Services Administration Contract GS-35F-43570, tasks EP0THO00393 and EP11HO00301 with General Dynamics Information Technology (GDIT), Henderson, NV. Although this work was reviewed by EPA and approved for publication, it may not necessarily reflect official Agency policy, nor does it represent the official views of GDIT. Mention of trade names or commercial products does not constitute endorsement or recommendation for use.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2012 Springer Science+Business Media, LLC
About this chapter
Cite this chapter
Knaak, J.B. et al. (2012). Parameters for Pyrethroid Insecticide QSAR and PBPK/PD Models for Human Risk Assessment. In: Whitacre, D. (eds) Reviews of Environmental Contamination and Toxicology. Reviews of Environmental Contamination and Toxicology, vol 219. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-3281-4_1
Download citation
DOI: https://doi.org/10.1007/978-1-4614-3281-4_1
Published:
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4614-3280-7
Online ISBN: 978-1-4614-3281-4
eBook Packages: Earth and Environmental ScienceEarth and Environmental Science (R0)