Contribution of aldehyde oxidase to methotrexate-induced hepatotoxicity: in vitro and pharmacoepidemiological approaches

References

• Weinblatt ME, Coblyn JS, Fox DA, et al. Efficacy of low-dose methotrexate in rheumatoid arthritis. N Engl J Med. 1985;312(13):818–822. doi: 10.1056/NEJM198503283121303
   PubMed Web of Science ®Google Scholar
• Jolivet J, Cowan KH, Curt GA, et al. The pharmacology and clinical use of methotrexate. N Engl J Med. 1983;309(18):1094–1104. doi: 10.1056/NEJM198311033091805
   PubMed Web of Science ®Google Scholar
• Stoller RG, Hande KR, Jacobs SA, et al. Use of plasma pharmacokinetics to predict and prevent methotrexate toxicity. N Engl J Med. 1977;297(12):630–634. doi: 10.1056/NEJM197709222971203
   PubMed Web of Science ®Google Scholar
• Jordan CG, Rashidi MR, Laljee H, et al. Aldehyde oxidase-catalysed oxidation of methotrexate in the liver of guinea-pig, rabbit and man. J Pharm Pharmacol. 1999;51(4):411–418. doi: 10.1211/0022357991772619
   PubMed Web of Science ®Google Scholar
• Ezhilarasan D. Hepatotoxic potentials of methotrexate: understanding the possible toxicological molecular mechanisms. Toxicology. 2021;458:152840. doi: 10.1016/j.tox.2021.152840
   PubMed Web of Science ®Google Scholar
• van de Meeberg MM, Fidder HH, Oldenburg B, et al. Therapeutic drug monitoring of methotrexate in patients with Crohn’s disease. Aliment Pharmacol Ther. 2023;58(11–12):1151–1162. doi: 10.1111/apt.17719
   PubMed Web of Science ®Google Scholar
• Vlaming ML, Pala Z, van Esch A, et al. Functionally overlapping roles of Abcg2 (Bcrp1) and Abcc2 (Mrp2) in the elimination of methotrexate and its main toxic metabolite 7-hydroxymethotrexate in vivo. Clin Cancer Res. 2009;15(9):3084–3093. doi: 10.1158/1078-0432.CCR-08-2940
   PubMed Web of Science ®Google Scholar
• Vlaming ML, van Esch A, Pala Z, et al. Abcc2 (Mrp2), Abcc3 (Mrp3), and Abcg2 (Bcrp1) are the main determinants for rapid elimination of methotrexate and its toxic metabolite 7-hydroxymethotrexate in vivo. Mol Cancer Ther. 2009;8(12):3350–3359. doi: 10.1158/1535-7163.MCT-09-0668
   PubMed Web of Science ®Google Scholar
• Ikemura K, Hiramatsu SI, Shinogi Y, et al. Concomitant febuxostat enhances methotrexate-induced hepatotoxicity by inhibiting breast cancer resistance protein. Sci Rep. 2019;9(1):20359. doi: 10.1038/s41598-019-56900-2
   PubMedGoogle Scholar
• Garattini E, Fratelli M, Terao M. The mammalian aldehyde oxidase gene family. Hum Genomics. 2009;4(2):119–130. doi: 10.1186/1479-7364-4-2-119
   PubMedGoogle Scholar
• Fu C, Di L, Han X, et al. Aldehyde oxidase 1 (AOX1) in human liver cytosols: quantitative characterization of AOX1 expression level and activity relationship. Drug Metab Dispos. 2013;41(10):1797–1804. doi: 10.1124/dmd.113.053082
   PubMed Web of Science ®Google Scholar
• Obach RS, Huynh P, Allen MC, et al. Human liver aldehyde oxidase: inhibition by 239 drugs. J Clin Pharmacol. 2004;44(1):7–19. doi: 10.1177/0091270003260336
   PubMed Web of Science ®Google Scholar
• Demir E, Sütcüoğlu O, Demir B, et al. A possible interaction between favipiravir and methotrexate: drug-induced hepatotoxicity in a patient with osteosarcoma. J Oncol Pharm Pract. 2022;28(2):445–448. doi: 10.1177/10781552211031304
   PubMed Web of Science ®Google Scholar
• Morgan SL, Baggott JE. The importance of inhibition of a catabolic pathway of methotrexate metabolism in its efficacy for rheumatoid arthritis. Med Hypotheses. 2019;122:10–15. doi: 10.1016/j.mehy.2018.10.002
   PubMed Web of Science ®Google Scholar
• Ueda H, Narumi K, Furugen A, et al. The rs35217482 (T755I) single-nucleotide polymorphism in aldehyde oxidase-1 attenuates protein dimer formation and reduces the rates of phthalazine metabolism. Drug Metab Dispos. 2022;50(9):1126–1131. doi: 10.1124/dmd.122.000902
   Web of Science ®Google Scholar
• Ueda H, Narumi K, Sato Y, et al. Evaluation of possible pharmacokinetic interaction between methotrexate and proton pump inhibitors in rats. Pharmacol Rep. 2020;72(5):1426–1432. doi: 10.1007/s43440-020-00130-1
   PubMed Web of Science ®Google Scholar
• Mei S, Cui Y, Zhang D, et al. Simultaneous determination of urine methotrexate, 7-hydroxy methotrexate, deoxyaminopteroic acid, and 7-hydroxy deoxyaminopteroic acid by UHPLC-MS/MS in patients receiving high-dose methotrexate therapy. Anal Sci. 2020;36(12):1479–1483. doi: 10.2116/analsci.19P481
   PubMed Web of Science ®Google Scholar
• U.S. Food and Drug Administration. In vitro drug interaction studies – cytochrome P450 enzyme- and transporter-mediated drug interactions. Guidance for industry [Internet]. 2020. [cited 2023 Apr 15]. Available from: https://www.fda.gov/media/134582/download
   Google Scholar
• Vieira ML, Kirby B, Ragueneau-Majlessi I, et al. 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. 2014;95(2):189–198. doi: 10.1038/clpt.2013.187
   PubMed Web of Science ®Google Scholar
• Bate A, Evans SJW. Quantitative signal detection using spontaneous ADR reporting. Pharmacoepidemiol Drug Saf. 2009;18:427–436. doi: 10.1002/pds.1742
   PubMed Web of Science ®Google Scholar
• Almenoff JS, DuMouchel W, Kindman LA, et al. Disproportionality analysis using empirical Bayes data mining: a tool for the evaluation of drug interactions in the post-marketing setting. Pharmacoepidemiol Drug Saf. 2003;12:517–521. doi: 10.1002/pds.885
   PubMed Web of Science ®Google Scholar
• Noguchi Y, Yoshizawa S, Aoyama K, et al. Verification of the “upward variation in the reporting odds ratio scores” to detect the signals of drug–drug interactions. Pharmaceutics. 2021;13(10):1531. doi: 10.3390/pharmaceutics13101531
   PubMed Web of Science ®Google Scholar
• Noguchi Y, Takaoka M, Hayashi T, et al. Antiepileptic combination therapy with Stevens-Johnson syndrome and toxic epidermal necrolysis: analysis of a Japanese pharmacovigilance database. Epilepsia. 2020;61(9):1979–1989. doi: 10.1111/epi.16626
   PubMed Web of Science ®Google Scholar
• Zhong G, Seaman CJ, Paragas EM, et al. Aldehyde oxidase contributes to all-trans-retinoic acid biosynthesis in human liver. Drug Metab Dispos. 2021;49(3):202–211. doi: 10.1124/dmd.120.000296
   PubMed Web of Science ®Google Scholar
• Sigruener A, Buechler C, Orsó E, et al. Human aldehyde oxidase 1 interacts with ATP-binding cassette transporter-1 and modulates its activity in hepatocytes. Horm Metab Res. 2007;39(11):781–789. doi: 10.1055/s-2007-992129
   PubMed Web of Science ®Google Scholar
• Dalvie D, Di L. Aldehyde oxidase and its role as a drug metabolizing enzyme. Pharmacol Ther. 2019;201:137–180. doi: 10.1016/j.pharmthera.2019.05.011
   PubMed Web of Science ®Google Scholar
• Farquhar D, Loo TL, Vadlamudi S. Synthesis and biologic evaluation of 7-hydroxymethotrexate, 7-methylaminopterin, and 7-methylmethotrexate. J Med Chem. 1972;15(5):567–569. doi: 10.1021/jm00275a038
   PubMed Web of Science ®Google Scholar
• Kochanek SJ, Close DA, Wang AX, et al. Confirmation of selected synergistic cancer drug combinations identified in an HTS campaign and exploration of drug efflux transporter contributions to the mode of synergy. SLAS Discov. 2019;24(6):653–668. doi: 10.1177/2472555219844566
   PubMed Web of Science ®Google Scholar
• Xiong L, Feng Y, Hu W, et al. Expression of AOX1 predicts prognosis of clear cell renal cell carcinoma. Front Genet. 2021;12:683173. doi: 10.3389/fgene.2021.683173
   PubMedGoogle Scholar
• Tan WK, Tan ARY, Sivanandam P, et al. In vitro inhibition of human aldehyde oxidase activity by clinically relevant concentrations of gefitinib and erlotinib: comparison with select metabolites, molecular docking analysis, and impact on hepatic metabolism of zaleplon and methotrexate. J Pharmacol Exp Ther. 2020;374(2):295–307. doi: 10.1124/jpet.120.265249
   PubMed Web of Science ®Google Scholar
• Plasencia-García BO, Rodríguez-Menéndez G, Rico-Rangel MI, et al. Drug-drug interactions between COVID-19 treatments and antipsychotics drugs: integrated evidence from 4 databases and a systematic review. Psychopharmacol (Berl). 2021;238(2):329–340. doi: 10.1007/s00213-020-05716-4
   PubMed Web of Science ®Google Scholar
• Ueda H, Narumi K, Asano S, et al. Comparative study on the occurrence of adverse effects in the concomitant use of azathioprine and aldehyde oxidase inhibitors. Expert Opin Drug Saf. 2023;23(1):89–97. doi: 10.1080/14740338.2023.2295976
   PubMed Web of Science ®Google Scholar
• Galiano Rus S, Ortiz García de la Foz V, Arias-Loste MT, et al. Elevated risk of liver steatosis in first-episode psychosis patients: results from a 3-year prospective study. Schizophr Res. 2022;246:30–38. doi: 10.1016/j.schres.2022.06.001
   PubMed Web of Science ®Google Scholar
• Di Martino V, Verhoeven DW, Verhoeven F, et al. Busting the myth of methotrexate chronic hepatotoxicity. Nat Rev Rheumatol. 2023;19(2):96–110. doi: 10.1038/s41584-022-00883-4
   PubMed Web of Science ®Google Scholar
• Winograd B, Lippens RJ, Oosterbaan MJ, et al. Renal excretion and pharmacokinetics of methotrexate and 7-hydroxy-methotrexate following a 24-h high dose infusion of methotrexate in children. Eur J Clin Pharmacol. 1986;30(2):231–238. doi: 10.1007/BF00614310
   PubMed Web of Science ®Google Scholar
• Erttmann R, Bielack S, Landbeck G. 7-hydroxy-methotrexate and clinical toxicity following high-dose methotrexate therapy. J Cancer Res Clin Oncol. 1985;109(1):86–88. doi: 10.1007/BF01884261
   PubMed Web of Science ®Google Scholar
• Foti A, Hartmann T, Coelho C, et al. Optimization of the expression of human aldehyde oxidase for investigations of single-nucleotide polymorphisms. Drug Metab Dispos. 2016;44(8):1277–1285. doi: 10.1124/dmd.115.068395
   PubMed Web of Science ®Google Scholar
• Danan G, Teschke R. RUCAM in drug and herb induced liver injury: the update. Int J Mol Sci. 2015;17(1):14. doi: 10.3390/ijms17010014
   PubMed Web of Science ®Google Scholar