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Xenobiotica
the fate of foreign compounds in biological systems
Volume 42, 2012 - Issue 12
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Pharmacogenetics

Bioactivation of chlorpyrifos by CYP2B6 variants

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Pages 1255-1262 | Received 18 Apr 2012, Accepted 08 Jun 2012, Published online: 10 Jul 2012

References

  • Berköz M, Yalin S. (2009). Association of CYP2B6 G15631T polymorphism with acute leukemia susceptibility. Leuk Res 33:919–923.
  • Buratti FM, Volpe MT, Fabrizi L, Meneguz A, Vittozzi L, Testai E. (2002a). Kinetic parameters of OPT pesticide desulfuration by c-DNA expressed human CYPs. Environ Toxicol Pharmacol 11:181–190.
  • Buratti FM, Volpe MT, Meneguz A, Vittozzi L, Testai E. (2002b). CYP-specific bioactivation of four organophosphorothioate pesticides by human lvier microsomes. Toxicol Appl Pharmacol, 186, 143–154.
  • Buratti FM, Volpe MT, Meneguz A, Vittozzi L, Testai E. (2003). CYP-specific bioactivation of four organophosphorothioate pesticides by human liver microsomes. Toxicol Appl Pharmacol 186:143–154.
  • Burk O, Arnold KA, Nussler AK, Schaeffeler E, Efimova E, Avery BA, Avery MA, Fromm MF, Eichelbaum M. (2005). Antimalarial artemisinin drugs induce cytochrome P450 and MDR1 expression by activation of xenosensors pregnane X receptor and constitutive androstane receptor. Mol Pharmacol 67:1954–1965.
  • Crane AL, Klein K, Zanger UM, Olson JR. (2012). Effect of CYP2B6*6 and CYP2C19*2 genotype on chlorpyrifos metabolism. Toxicology 293:115–122.
  • Croom EL, Wallace AD, Hodgson E. (2010). Human variation in CYP-specific chlorpyrifos metabolism. Toxicology 276:184–191.
  • Desta Z, Saussele T, Ward B, Blievernicht J, Li L, Klein K, Flockhart DA, Zanger UM. (2007). Impact of CYP2B6 polymorphism on hepatic efavirenz metabolism in vitro. Pharmacogenomics 8:547–558.
  • Eyer F, Roberts DM, Buckley NA, Eddleston M, Thiermann H, Worek F, Eyer P. (2009). Extreme variability in the formation of chlorpyrifos oxon (CPO) in patients poisoned by chlorpyrifos (CPF). Biochem Pharmacol 78:531–537.
  • Faucette SR, Zhang TC, Moore R, Sueyoshi T, Omiecinski CJ, LeCluyse EL, Negishi M, Wang H. (2007). Relative activation of human pregnane X receptor versus constitutive androstane receptor defines distinct classes of CYP2B6 and CYP3A4 inducers. J Pharmacol Exp Ther 320:72–80.
  • 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.
  • Foxenberg RJ, McGarrigle BP, Knaak JB, Kostyniak PJ, Olson JR. (2007). Human hepatic cytochrome p450-specific metabolism of parathion and chlorpyrifos. Drug Metab Dispos 35:189–193.
  • Gatanaga H, Hayashida T, Tsuchiya K, Yoshino M, Kuwahara T, Tsukada H, Fujimoto K, Sato I, Ueda M, Horiba M, Hamaguchi M, Yamamoto M, Takata N, Kimura A, Koike T, Gejyo F, Matsushita S, Shirasaka T, Kimura S, Oka S. (2007). Successful efavirenz dose reduction in HIV type 1-infected individuals with cytochrome P450 2B6 *6 and *26. Clin Infect Dis 45:1230–1237.
  • Gervot L, Rochat B, Gautier JC, Bohnenstengel F, Kroemer H, de Berardinis V, Martin H, Beaune P, de Waziers I. (1999). Human CYP2B6: expression, inducibility and catalytic activities. Pharmacogenetics 9:295–306.
  • Goodwin B, Moore LB, Stoltz CM, McKee DD, Kliewer SA. (2001). Regulation of the human CYP2B6 gene by the nuclear pregnane X receptor. Mol Pharmacol 60:427–431.
  • Hodgson E, Rose RL. (2007). The importance of cytochrome P450 2B6 in the human metabolism of environmental chemicals. Pharmacol Ther 113:420–428.
  • Honda M, Muroi Y, Tamaki Y, Saigusa D, Suzuki N, Tomioka Y, Matsubara Y, Oda A, Hirasawa N, Hiratsuka M. (2011). Functional characterization of CYP2B6 allelic variants in demethylation of antimalarial artemether. Drug Metab Dispos 39:1860–1865.
  • Jinno H, Tanaka-Kagawa T, Ohno A, Makino Y, Matsushima E, Hanioka N, Ando M. (2003). Functional characterization of cytochrome P450 2B6 allelic variants. Drug Metab Dispos 31:398–403.
  • Joo H, Choi K, Rose RL, Hodgson E. (2007). Inhibition of fipronil and nonane metabolism in human liver microsomes and human cytochrome P450 isoforms by chlorpyrifos. J Biochem Mol Toxicol 21:76–80.
  • Kirchheiner J, Klein C, Meineke I, Sasse J, Zanger UM, Mürdter TE, Roots I, Brockmöller J. (2003). Bupropion and 4-OH-bupropion pharmacokinetics in relation to genetic polymorphisms in CYP2B6. Pharmacogenetics 13:619–626.
  • Klein K, Lang T, Saussele T, Barbosa-Sicard E, Schunck WH, Eichelbaum M, Schwab M, Zanger UM. (2005). Genetic variability of CYP2B6 in populations of African and Asian origin: allele frequencies, novel functional variants, and possible implications for anti-HIV therapy with efavirenz. Pharmacogenet Genomics 15:861–873.
  • Lang T, Klein K, Fischer J, Nüssler AK, Neuhaus P, Hofmann U, Eichelbaum M, Schwab M, Zanger UM. (2001). Extensive genetic polymorphism in the human CYP2B6 gene with impact on expression and function in human liver. Pharmacogenetics 11:399–415.
  • Lang T, Klein K, Richter T, Zibat A, Kerb R, Eichelbaum M, Schwab M, Zanger UM. (2004). Multiple novel nonsynonymous CYP2B6 gene polymorphisms in Caucasians: demonstration of phenotypic null alleles. J Pharmacol Exp Ther 311:34–43.
  • Mehlotra RK, Bockarie MJ, Zimmerman PA. (2007). CYP2B6 983T>C polymorphism is prevalent in West Africa but absent in Papua New Guinea: implications for HIV/AIDS treatment. Br J Clin Pharmacol 64:391–395.
  • Miksys S, Lerman C, Shields PG, Mash DC, Tyndale RF. (2003). Smoking, alcoholism and genetic polymorphisms alter CYP2B6 levels in human brain. Neuropharmacology 45:122–132.
  • Mo SL, Liu YH, Duan W, Wei MQ, Kanwar JR, Zhou SF. (2009). Substrate specificity, regulation, and polymorphism of human cytochrome P450 2B6. Curr Drug Metab 10:730–753.
  • Mutch E, Williams FM. (2006). Diazinon, chlorpyrifos and parathion are metabolised by multiple cytochromes P450 in human liver. Toxicology 224:22–32.
  • Nakajima M, Komagata S, Fujiki Y, Kanada Y, Ebi H, Itoh K, Mukai H, Yokoi T, Minami H. (2007). Genetic polymorphisms of CYP2B6 affect the pharmacokinetics/pharmacodynamics of cyclophosphamide in Japanese cancer patients. Pharmacogenet Genomics 17:431–445.
  • Sams C, Cocker J, Lennard MS. (2004). Biotransformation of chlorpyrifos and diazinon by human liver microsomes and recombinant human cytochrome P450s (CYP). Xenobiotica 34:861–873.
  • Smith JN, Timchalk C, Bartels MJ, Poet TS. (2011). In vitro age-dependent enzymatic metabolism of chlorpyrifos and chlorpyrifos-oxon in human hepatic microsomes and chlorpyrifos-oxon in plasma. Drug Metab Dispos 39:1353–1362.
  • Sueyoshi T, Kawamoto T, Zelko I, Honkakoski P, Negishi M. (1999). The repressed nuclear receptor CAR responds to phenobarbital in activating the human CYP2B6 gene. J Biol Chem 274:6043–6046.
  • Tang J, Cao Y, Rose RL, Brimfield AA, Dai D, Goldstein JA, Hodgson E. (2001). Metabolism of chlorpyrifos by human cytochrome P450 isoforms and human, mouse, and rat liver microsomes. Drug Metab Dispos 29:1201–1204.
  • US EPA. (2000). Chlorpyrifos Revised Risk Assessment and Agreement with Registrants. Washington, DC, U.S. Environmental Protection Agency.
  • Viljoen M, Karlsson MO, Meyers TM, Gous H, Dandara C, Rheeders M. (2012). Influence of CYP2B6 516G>T polymorphism and interoccasion variability (IOV) on the population pharmacokinetics of efavirenz in HIV-infected South African children. Eur J Clin Pharmacol 68:339–347.
  • Walsky RL, Astuccio AV, Obach RS. (2006). Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol 46:1426–1438.
  • Wang H, Tompkins LM. (2008). CYP2B6: new insights into a historically overlooked cytochrome P450 isozyme. Curr Drug Metab 9:598–610.
  • Wang J, Sönnerborg A, Rane A, Josephson F, Lundgren S, Ståhle L, Ingelman-Sundberg M. (2006). Identification of a novel specific CYP2B6 allele in Africans causing impaired metabolism of the HIV drug efavirenz. Pharmacogenet Genomics 16:191–198.
  • Wyen C, Hendra H, Siccardi M, Platten M, Jaeger H, Harrer T, Esser S, Bogner JR, Brockmeyer NH, Bieniek B, Rockstroh J, Hoffmann C, Stoehr A, Michalik C, Dlugay V, Jetter A, Knechten H, Klinker H, Skaletz-Rorowski A, Fätkenheuer G, Egan D, Back DJ, Owen A; German Competence Network for HIV/AIDS Coordinators. (2011). Cytochrome P450 2B6 (CYP2B6) and constitutive androstane receptor (CAR) polymorphisms are associated with early discontinuation of efavirenz-containing regimens. J Antimicrob Chemother 66:2092–2098.

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