Evaluation of species differences in the metabolism of the selective Na_V1.7 inhibitor DS-1971a, a mixed substrate of cytochrome P450 and aldehyde oxidase

References

• Anderson S, Luffer-Atlas D, Knadler MP. 2009. Predicting circulating human metabolites: how good are we? Chem Res Toxicol. 22(2):243–256.
   PubMed Web of Science ®Google Scholar
• Austin NE, Baldwin SJ, Cutler L, Deeks N, Kelly PJ, Nash M, Shardlow CE, Stemp G, Thewlis K, Ayrton A, et al. 2001. Pharmacokinetics of the novel, high-affinity and selective dopamine D3 receptor antagonist SB-277011 in rat, dog and monkey: in vitro/in vivo correlation and the role of aldehyde oxidase. Xenobiotica. 31(8–9):677–686.
   PubMed Web of Science ®Google Scholar
• Behera D, Pattem R, Gudi G. 2014. Effect of commonly used organic solvents on aldehyde oxidase-mediated vanillin, phthalazine and methotrexate oxidation in human, rat and mouse liver subcellular fractions. Xenobiotica. 44(8):722–733.
   PubMed Web of Science ®Google Scholar
• Crouch RD, Hutzler JM, Daniels JS. 2018. A novel in vitro allometric scaling methodology for aldehyde oxidase substrates to enable selection of appropriate species for traditional allometry. Xenobiotica. 48(3):219–231.
   PubMed Web of Science ®Google Scholar
• Crouch RD, Morrison RD, Byers FW, Lindsley CW, Emmitte KA, Daniels JS. 2016. Evaluating the disposition of a mixed aldehyde oxidase/cytochrome P450 substrate in rats with attenuated P450 activity. Drug Metab Dispos. 44(8):1296–1303.
   PubMed Web of Science ®Google Scholar
• Dalvie D, Obach RS, Kang P, Prakash C, Loi CM, Hurst S, Nedderman A, Goulet L, Smith E, Bu HZ, et al. 2009. Assessment of three human in vitro systems in the generation of major human excretory and circulating metabolites. Chem Res Toxicol. 22(2):357–368.
   PubMed Web of Science ®Google Scholar
• Dalvie D, Xiang C, Kang P, Zhou S. 2013. Interspecies variation in the metabolism of zoniporide by aldehyde oxidase. Xenobiotica. 43(5):399–408.
   PubMed Web of Science ®Google Scholar
• Diamond S, Boer J, Maduskuie TP Jr, Falahatpisheh N, Li Y, Yeleswaram S. 2010. Species-specific metabolism of SGX523 by aldehyde oxidase and the toxicological implications. Drug Metab Dispos. 38(8):1277–1285.
   PubMed Web of Science ®Google Scholar
• Duley JA, Harris O, Holmes RS. 1985. Analysis of human alcohol- and aldehyde-metabolising isozymes by electrophoresis and isoelectric focusing. Alcohol Clin Exp Res. 9(3):263–271.
   PubMed Web of Science ®Google Scholar
• Food and Drug Administration (FDA). 2020. Guidance for industry: safety testing of drug metabolites. Silver Spring, MD: Department of Health and Human Services, Center for Drug Evaluation and Research, U.S. Food and Drug Administration, U.S.
   Google Scholar
• Foti RS, Dalvie DK. 2016. Cytochrome P450 and non-cytochrome P450 oxidative metabolism: contributions to the pharmacokinetics, safety, and efficacy of xenobiotics. Drug Metab Dispos. 44(8):1229–1245.
   PubMed Web of Science ®Google Scholar
• Inoue K, Mizuo H, Kawaguchi S, Fukuda K, Kusano K, Yoshimura T. 2014. Oxidative metabolic pathway of lenvatinib mediated by aldehyde oxidase. Drug Metab Dispos. 42(8):1326–1333.
   PubMed Web of Science ®Google Scholar
• International Conference on Harmonization (ICH) M3(R2) guidance. 2010. Nonclinical Safety Studies for the Conduct of Human Clinical Trials and Marketing Authorization for Pharmaceuticals. Geneva, Switzerland: The International Council for Harmonisation of Technical Requirements for Pharmaceuticals for Human Use.
   Google Scholar
• Kamimura H, Nakada N, Suzuki K, Mera A, Souda K, Murakami Y, Tanaka K, Iwatsubo T, Kawamura A, Usui T. 2010. Assessment of chimeric mice with humanized liver as a tool for predicting circulating human metabolites. Drug Metab Pharmacokinet. 25(3):223–235.
   PubMed Web of Science ®Google Scholar
• Kawashima K, Hosoi K, Naruke T, Shiba T, Kitamura M, Watabe T. 1999. Aldehyde oxidase-dependent marked species difference in hepatic metabolism of the sedative-hypnotic, zaleplon, between monkeys and rats. Drug Metab Dispos. 27(3):422–428.
   PubMed Web of Science ®Google Scholar
• Kilford PJ, Stringer R, Sohal B, Houston JB, Galetin A. 2009. Prediction of drug clearance by glucuronidation from in vitro data: use of combined cytochrome P450 and UDP-glucuronosyltransferase cofactors in alamethicin-activated human liver microsomes. Drug Metab Dispos. 37(1):82–89.
   PubMed Web of Science ®Google Scholar
• Ma RSY, Kayani K, Whyte-Oshodi D, Whyte-Oshodi A, Nachiappan N, Gnanarajah S, Mohammed R. 2019. Voltage gated sodium channels as therapeutic targets for chronic pain. J Pain Res. 12:2709–2722.
   PubMed Web of Science ®Google Scholar
• Mota C, Coelho C, Leimkuhler S, Garattini E, Terao M, Santos-Silva T, Romao MJ. 2018. Critical overview on the structure and metabolism of human aldehyde oxidase and its role in pharmacokinetics. Coord Chem Rev. 368:35–59.
   Web of Science ®Google Scholar
• Sakai C, Iwano S, Yamazaki Y, Ando A, Nakane F, Kouno M, Yamazaki H, Miyamoto Y. 2014. Species differences in the pharmacokinetic parameters of cytochrome P450 probe substrates between experimental animals, such as mice, rats, dogs, monkeys, and microminipigs, and humans. J Drug Metab Toxicol. 5:1–12.
   Google Scholar
• Sanoh S, Ohta S. 2014. Chimeric mice transplanted with human hepatocytes as a model for prediction of human drug metabolism and pharmacokinetics. Biopharm Drug Dispos. 35(2):71–86.
   PubMed Web of Science ®Google Scholar
• Schadt S, Bister B, Chowdhury SK, Funk C, Hop C, Humphreys WG, Igarashi F, James AD, Kagan M, Khojasteh SC, et al. 2018. A decade in the MIST: learnings from investigations of drug metabolites in drug development under the ‘Metabolites in Safety Testing’ regulatory guidance. Drug Metab Dispos. 46(6):865–878.
   PubMed Web of Science ®Google Scholar
• Schofield PC, Robertson IG, Paxton JW. 2000. Inter-species variation in the metabolism and inhibition of N-[(2'-dimethylamino)ethyl]acridine-4-carboxamide (DACA) by aldehyde oxidase. Biochem Pharmacol. 59(2):161–165.
   PubMed Web of Science ®Google Scholar
• Shinozuka T, Kobayashi H, Suzuki S, Tanaka K, Karanjule N, Hayashi N, Tsuda T, Tokumaru E, Inoue M, Ueda K, et al. 2020. Discovery of DS-1971a, a potent, selective NaV1.7 inhibitor. J Med Chem. 63(18):10204–10220.
   PubMed Web of Science ®Google Scholar
• Soucek P, Zuber R, Anzenbacherova E, Anzenbacher P, Guengerich FP. 2001. Minipig cytochrome P450 3A, 2A and 2C enzymes have similar properties to human analogs. BMC Pharmacol. 1(1):11.
   PubMedGoogle Scholar
• Terao M, Kurosaki M, Barzago MM, Varasano E, Boldetti A, Bastone A, Fratelli M, Garattini E. 2006. Avian and canine aldehyde oxidases. Novel insights into the biology and evolution of molybdo-flavoenzymes. J Biol Chem. 281(28):19748–19761.
   PubMed Web of Science ®Google Scholar
• Van Hecke O, Austin SK, Khan RA, Smith BH, Torrance N. 2014. Neuropathic pain in the general population: a systematic review of epidemiological studies. Pain. 155(4):654–662.
   PubMed Web of Science ®Google Scholar
• Yan Z, Caldwell GW. 2003. Metabolic assessment in liver microsomes by co-activating cytochrome P450s and UDP-glycosyltransferases. Eur J Drug Metab Pharmacokinet. 28(3):223–232.
   PubMed Web of Science ®Google Scholar
• Yoshimatsu H, Konno Y, Ishii K, Satsukawa M, Yamashita S. 2016. Usefulness of minipigs for predicting human pharmacokinetics: prediction of distribution volume and plasma clearance. Drug Metab Pharmacokinet. 31(1):73–81.
   PubMed Web of Science ®Google Scholar
• Zanger UM, Schwab M. 2013. Cytochrome P450 enzymes in drug metabolism: regulation of gene expression, enzyme activities, and impact of genetic variation. Pharmacol Ther. 138(1):103–141.
   PubMed Web of Science ®Google Scholar
• Zientek M, Jiang Y, Youdim K, Obach RS. 2010. In vitro-in vivo correlation for intrinsic clearance for drugs metabolized by human aldehyde oxidase. Drug Metab Dispos. 38(8):1322–1327.
   PubMed Web of Science ®Google Scholar