Unveiling CYP450 inhibition by the pesticide prothioconazole through integrated in vitro studies and PBPK modeling

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. https://doi.org/10.1124/dmd.30.12.1497

Article  PubMed  CAS  Google Scholar 

Bayer CropScience (2017) Summary of the toxicological and metabolism studies for Prothioconazole. https://www.bayer.com/sites/default/files/M-539810-04-4.PDF. Accessed 01 December 2022

Carrão DB, Habenchus MD, de Albuquerque NCP, da Silva RM, Lopes NP, de Oliveira ARM (2019) In vitro inhibition of human CYP2D6 by the chiral pesticide fipronil and its metabolite fipronil sulfone: Prediction of pesticide-drug interactions. Toxicol Lett 313:196–204. https://doi.org/10.1016/j.toxlet.2019.07.005

Article  PubMed  CAS  Google Scholar 

Casida JE (2017) Why prodrugs and propesticides succeed. Chem Res Toxicol 30:1117–1126. https://doi.org/10.1021/acs.chemrestox.7b00030

Article  PubMed  CAS  Google Scholar 

Casida JE, Durkin KA (2017) Pesticide chemical research in toxicology: lessons from nature. Chem Res Toxicol 30:94–104. https://doi.org/10.1021/acs.chemrestox.6b00303

Article  PubMed  CAS  Google Scholar 

de Albuquerque NCP, Carrão DB, Habenschus MD, Fonseca FS, Moreira da Silva R, Lopes NP, Rocha BA, Barbosa Júnior F, de Oliveira ARM (2020) Risk assessment of the chiral pesticide fenamiphos in a human model: cytochrome P450 phenotyping and inhibition studies. Food and Chem Toxicol 146:111826. https://doi.org/10.1016/j.fct.2020.111826

Article  CAS  Google Scholar 

EFSA (2007) Conclusion regarding the peer review of the pesticide risk assessment of the active substance prothioconazole. EFSA J 5:106r. https://doi.org/10.2903/j.efsa.2007.106r

Article  Google Scholar 

EMA (2012) Guideline on the Investigation of Drug Interactions. https://www.ema.europa.eu/en/documents/scientific-guideline/guideline-investigation-drug-interactions-revision-1_en.pdf. Accessed 05 April 2024

EPA (2007) Pesticide Fact Sheet - Prothioconazole. https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-113961_14-Mar-07.pdf. Accessed 01 July 2022

EPA (2024) CompTox Chemicals Dashboard. https://comptox.epa.gov/dashboard/chemical/adme-ivive-subtab/DTXSID4034869?deepLink=22. Accessed 8 April 2024.

FDA (2020) In vitro drug interaction studies—cytochrome p450 enzyme- and transporter-mediated drug interactions guidance for industry. Guidance for Industry. https://www.fda.gov/media/134582/download. Accessed 05 April 2024

Gao B, Poma G, Malarvannan G, Dumitrascu C, Bastiaensen M, Wang M, Covaci A (2022) Development of an analytical method based on solid-phase extraction and LC-MS/MS for the monitoring of current-use pesticides and their metabolites in human urine. J Environ Sci 111:153–163. https://doi.org/10.1016/j.jes.2021.03.029

Article  CAS  Google Scholar 

Habenschus M, Moreira F, Lopes NP, de Oliveira ARM (2017) In Vitro Inhibition of Human CYP450s 1A2, 2C9, 3A4/5, 2D6 and 2E1 by Grandisin. Planta Med 83:727–736. https://doi.org/10.1055/s-0042-124615

Article  PubMed  CAS  Google Scholar 

Habenschus MD, Carrão DB, de Albuquerque NCP, Perovani IS, Moreira da Silva R, Nardini V, Lopes NP, Dias LG, Moraes de Oliveira AR (2021) In vitro enantioselective inhibition of the main human CYP450 enzymes involved in drug metabolism by the chiral pesticide tebuconazole. Toxicol Lett 351:1–9. https://doi.org/10.1016/j.toxlet.2021.08.006

Article  PubMed  CAS  Google Scholar 

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. https://doi.org/10.1124/dmd.105.007658

Article  PubMed  CAS  Google Scholar 

Paini A, Tan YM, Sachana M, Worth A (2021) Gaining acceptance in next generation PBK modelling approaches for regulatory assessments—an OECD international effort. Comput Toxicol 18:100163. https://doi.org/10.1016/j.comtox.2021.100163

Article  PubMed  PubMed Central  CAS  Google Scholar 

Pearce RG, Setzer RW, Strope CL, Sipes NS, Wambaugh JF (2017) httk: R package for high-throughput toxicokinetics. J Stat Softw. https://doi.org/10.18637/jss.v079.i04

Article  PubMed  PubMed Central  Google Scholar 

Perovani IS, Mariano Bucci JL, Carrão DB, Santos Barbetta MF, Moreira da Silva R, Lopes NP, Moraes de Oliveira AR (2021) Enantioselective inhibition of human CYP2C19 by the chiral pesticide ethofumesate: Prediction of pesticide-drug interactions in humans. Chem Biol Interact 345:109552. https://doi.org/10.1016/j.cbi.2021.109552

Article  PubMed  CAS  Google Scholar 

Perovani IS, Santos Barbetta MF, Moreira da Silva R, Lopes NP, Moraes de Oliveira AR (2022) In vitro-in vivo correlation of the chiral pesticide prothioconazole after interaction with human CYP450 enzymes. Food Chem Toxicol 163:112947. https://doi.org/10.1016/j.fct.2022.112947

Article  PubMed  CAS  Google Scholar 

Punekar NS (2018) Reversible Inhibitions. In: Punkear NS (ed) ENZYMES: catalysis, kinetics and mechanisms. Springer Singapore, Singapore, pp 245–257. https://doi.org/10.1007/978-981-13-0785-0_22

Chapter  Google Scholar 

Sinha VK, Snoeys J, Osselaer NV, Peer AV, Mackie C, Heald D (2012) From preclinical to human—prediction of oral absorption and drug–drug interaction potential using physiologically based pharmacokinetic (PBPK) modeling approach in an industrial setting: a workflow by using case example. Biopharm Drug Dispos 33:111–121. https://doi.org/10.1002/bdd.1782

Article  PubMed  CAS  Google Scholar 

Spaggiari D, Geiser L, Daali Y, Rudaz S (2014) A cocktail approach for assessing the in vitro activity of human cytochrome P450s: an overview of current methodologies. J Pharm Biomed Anal 101:221–237. https://doi.org/10.1016/j.jpba.2014.03.018

Article  PubMed  CAS  Google Scholar 

Theken KN, Lee CR, Gong L, Caudle KE, Formea CM, Gaedigk A, Klein TE, Agúndez JAG, Grosser T (2020) Clinical Pharmacogenetics Implementation Consortium Guideline (CPIC) for CYP2C9 and nonsteroidal anti-inflammatory drugs. Clin Pharmacol Ther 108:191–200. https://doi.org/10.1002/cpt.1830

Article  PubMed  Google Scholar 

Vieira MLT, Kirby B, Ragueneau-Majlessi I, Galetin A, Chien JYL, Einolf HJ, Fahmi OA, Fischer V, Fretland A, Grime K, Hall SD, Higgs R, Plowchalk D, Riley R, Seibert E, Skordos K, Snoeys J, Venkatakrishnan K, Waterhouse T, Obach RS, Berglund EG, Zhang L, Zhao P, Reynolds KS, Huang SM (2014) Evaluation of various static in vitro–in vivo extrapolation models for risk assessment of the CYP3A inhibition potential of an investigational drug. Clin Pharmacol Ther 95:189–198. https://doi.org/10.1038/clpt.2013.187

Article  PubMed  CAS  Google Scholar 

Watanabe R, Ohashi R, Esaki T, Kawashima H, Natsume-Kitatani Y, Nagao C, Mizuguchi K (2019) Development of an in silico prediction system of human renal excretion and clearance from chemical structure information incorporating fraction unbound in plasma as a descriptor. Sci Rep 9:18782. https://doi.org/10.1038/s41598-019-55325-1

Article  PubMed  PubMed Central  CAS  Google Scholar 

Zhou F, Dai L, Wei S, Cheng G, Li L (2015) Toxicokinetics and tissue distribution of prothioconazole in male adult Sprague-Dawley rats following a single oral administration. Xenobiotica 45:450–455. https://doi.org/10.3109/00498254.2014.988771

Article  PubMed  CAS  Google Scholar 

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