Assessing in vitro stability of remdesivir (GS-5734) and conversion to GS-441524 in feline plasma and whole blood

References

• Agency EM, Division HM. 2020. Remdesivir Gilead. Product No EMEA/H/K/5622/CU 03 April 2020. Summary on Compassionate Use.
   Google Scholar
• Agostini ML, Andres EL, Sims AC, Graham RL, Sheahan TP, Lu X, Smith EC, Case JB, Feng JY, Jordan R, et al. 2018. Coronavirus susceptibility to the antiviral remdesivir (GS-5734) is mediated by the viral polymerase and the proofreading exoribonuclease. mBio. 9(2):e00221–00218. doi: 10.1128/mBio.00221-18.
   PubMed Web of Science ®Google Scholar
• Avataneo V, de Nicolò A, Cusato J, Antonucci M, Manca A, Palermiti A, Waitt C, Walimbwa S, Lamorde M, di Perri G, et al. 2020. Development and validation of a UHPLC-MS/MS method for quantification of the prodrug remdesivir and its metabolite GS-441524: a tool for clinical pharmacokinetics of SARS-CoV-2/COVID-19 and Ebola virus disease. J Antimicrob Chemother. 75(7):1772–1777. doi: 10.1093/jac/dkaa152.
   PubMed Web of Science ®Google Scholar
• Bahar FG, Ohura K, Ogihara T, Imai T. 2012. Species difference of esterase expression and hydrolase activity in plasma. J Pharm Sci. 101(10):3979–3988. doi: 10.1002/jps.23258.
   PubMed Web of Science ®Google Scholar
• Balzarini J, Keyaerts E, Vijgen L, Vandermeer F, Stevens M, De Clercq E, Egberink H, Van Ranst M. 2005. Pyridine N-oxide derivatives are inhibitory to the human SARS and feline infectious peritonitis coronavirus in cell ­culture. J Antimicrob Chemother. 57(3):472–481. doi: 10.1093/jac/dki481.
   PubMed Web of Science ®Google Scholar
• Barlough JE, Shacklett BL. 1994. Antiviral studies of feline infectious peritonitis virus in vitro. Vet Rec. 135(8):177–179. doi: 10.1136/vr.135.8.177.
   PubMed Web of Science ®Google Scholar
• Cho A, Saunders OL, Butler T, Zhang L, Xu J, Vela JE, Feng JY, Ray AS, Kim CU. 2012. Synthesis and antiviral activity of a series of 1′-substituted 4-aza-7,9-dideazaadenosine C-nucleosides. Bioorg Med Chem Lett. 22(8):2705–2707. doi: 10.1016/j.bmcl.2012.02.105.
   PubMed Web of Science ®Google Scholar
• Coggins SJ, Norris JM, Malik R, Govendir M, Hall EJ, Kimble B, Thompson MF. 2023. Outcomes of treatment of cats with feline infectious peritonitis using parenterally administered remdesivir, with or without transition to orally administered GS-441524. J Vet Intern Med. 37(5):1772–1783. doi: 10.1111/jvim.16803.
   PubMed Web of Science ®Google Scholar
• Cossum PA. 1988. Role of the red blood cell in drug metabolism. Biopharm Drug Dispos. 9(4):321–336. doi: 10.1002/bod.2510090402.
   PubMed Web of Science ®Google Scholar
• De Clercq E. 2004. Antivirals and antiviral strategies. Nat Rev Microbiol. 2(9):704–720. doi: 10.1038/nrmicro975.
   PubMed Web of Science ®Google Scholar
• Deb S, Reeves AA, Hopefl R, Bejusca R. 2021. ADME and pharmacokinetic properties of remdesivir: its drug interaction potential. Pharmaceuticals. 14(7):655. doi: 10.3390/ph14070655.
   Web of Science ®Google Scholar
• Eastman RT, Roth JS, Brimacombe KR, Simeonov A, Shen M, Patnaik S, Hall MD. 2020. Remdesivir: a review of its discovery and development leading to emergency use authorization for treatment of COVID-19. ACS Cent Sci. 6(5):672–683. doi: 10.1021/acscentsci.0c00489.
   PubMed Web of Science ®Google Scholar
• Gordon CJ, Tchesnokov EP, Woolner E, Perry JK, Feng JY, Porter DP, Götte M. 2020. Remdesivir is a direct-acting antiviral that inhibits RNA-dependent RNA polymerase from severe acute respiratory syndrome coronavirus 2 with high potency. J Biol Chem. 295(20):6785–6797. doi: 10.1074/jbc.RA120.013679.
   PubMed Web of Science ®Google Scholar
• Green J, Syme H, Tayler S. 2023. Thirty-two cats with effusive or non-effusive feline infectious peritonitis treated with a combination of remdesivir and GS-441524. J Vet Intern Med. 37(5):1784–1793. doi: 10.1111/jvim.16804.
   PubMed Web of Science ®Google Scholar
• Hartmann K, Ritz S. 2008. Treatment of cats with feline infectious peritonitis. Vet Immunol Immunopathol. 123(1–2):172–175. doi: 10.1016/j.vetimm.2008.01.026.
   PubMed Web of Science ®Google Scholar
• Hu W-J, Chang L, Yang Y, Wang X, Xie Y-C, Shen J-S, Tan B, Liu J. 2021. Pharmacokinetics and tissue distribution of remdesivir and its metabolites nucleotide monophosphate, nucleotide triphosphate, and nucleoside in mice. Acta Pharmacol Sin. 42(7):1195–1200. doi: 10.1038/s41401-020-00537-9.
   PubMed Web of Science ®Google Scholar
• Humeniuk R, Mathias A, Cao H, Osinusi A, Shen G, Chng E, Ling J, Vu A, German P. 2020. Safety, tolerability, and pharmacokinetics of remdesivir, an antiviral for treatment of COVID-19, in healthy subjects. Clin Transl Sci. 13(5):896–906. doi: 10.1111/cts.12840.
   PubMed Web of Science ®Google Scholar
• Jones S, Novicoff W, Nadeau J, Evans S. 2021. Unlicensed GS-441524-like antiviral therapy can be effective for at-home treatment of feline infectious peritonitis. Animals. 11(8):2257. doi: 10.3390/ani11082257.
   Web of Science ®Google Scholar
• Jordheim LP, Durantel D, Zoulim F, Dumontet C. 2013. Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases. Nat Rev Drug Discov. 12(6):447–464. doi: 10.1038/nrd4010.
   PubMed Web of Science ®Google Scholar
• Kimble B, Coggins SJ, Norris JM, Thompson MF, Govendir M. 2023. Quantification of GS-441524 concentration in feline plasma using high performance liquid chromatography with fluorescence detection. Vet Q. 43(1):1–9. doi: 10.1080/01652176.2023.2246553.
   PubMedGoogle Scholar
• Krentz D, Zenger K, Alberer M, Felten S, Bergmann M, Dorsch R, Matiasek K, Kolberg L, Hofmann-Lehmann R, Meli ML, et al. 2021. Curing cats with feline infectious peritonitis with an oral multi-component drug containing GS-441524. Viruses. 13(11):2228. doi: 10.3390/v13112228.
   PubMed Web of Science ®Google Scholar
• Li B, Sedlacek M, Manoharan I, Boopathy R, Duysen EG, Masson P, Lockridge O. 2005. Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem Pharmacol. 70(11):1673–1684. doi: 10.1016/j.bcp.2005.09.002.
   PubMed Web of Science ®Google Scholar
• Li Y, Cao L, Li G, Cong F, Li Y, Sun J, Luo Y, Chen G, Li G, Wang P, et al. 2022. Remdesivir metabolite GS-441524 effectively inhibits SARS-CoV-2 infection in mouse models. J Med Chem. 65(4):2785–2793. doi: 10.1021/acs.jmedchem.0c01929.
   PubMed Web of Science ®Google Scholar
• Murphy BG, Perron M, Murakami E, Bauer K, Park Y, Eckstrand C, Liepnieks M, Pedersen NC. 2018. The nucleoside analog GS-441524 strongly inhibits feline infectious peritonitis (FIP) virus in tissue culture and experimental cat infection studies. Vet Microbiol. 219:226–233. doi: 10.1016/j.vetmic.2018.04.026.
   PubMed Web of Science ®Google Scholar
• Obach RS, Baxter JG, Liston TE, et al. 1997. The prediction of human pharmacokinetic parameters from preclinical and in vitro metabolism data. J Pharmacol Exp Ther. 283:46–58.
   PubMed Web of Science ®Google Scholar
• Pedersen NC, Perron M, Bannasch M, Montgomery E, Murakami E, Liepnieks M, Liu H. 2019. Efficacy and safety of the nucleoside analog GS-441524 for treatment of cats with naturally occurring feline infectious peritonitis. J Feline Med Surg. 21(4):271–281. doi: 10.1177/1098612X19825701.
   PubMed Web of Science ®Google Scholar
• Pedersen NC. 2014. An update on feline infectious peritonitis: diagnostics and therapeutics. Vet J. 201(2):133–141. doi: 10.1016/j.tvjl.2014.04.016.
   PubMed Web of Science ®Google Scholar
• Périgaud C, Gosselin G, Imbach JL. 1992. Nucleoside analogues as chemotherapeutic agents: a review. Nucleosides Nucleotides. 11(2–4):903–945. doi: 10.1080/07328319208021748.
   Web of Science ®Google Scholar
• Rudakova EV, Boltneva NP, Makhaeva GF. 2011. Comparative analysis of esterase activities of human, mouse, and rat blood. Bull Exp Biol Med. 152(1):73–75. doi: 10.1007/s10517-011-1457-y.
   PubMed Web of Science ®Google Scholar
• Sheahan TP, Sims AC, Graham RL, Menachery VD, Gralinski LE, Case JB, Leist SR, Pyrc K, Feng JY, Trantcheva I, et al. 2017. Broad-spectrum antiviral GS-5734 inhibits both epidemic and zoonotic coronaviruses. Sci Transl Med. 9(396):eaal3653. doi: 10.1126/scitranslmed.aal3653.
   PubMed Web of Science ®Google Scholar
• Tempestilli M, Caputi P, Avataneo V, Notari S, Forini O, Scorzolini L, Marchioni L, Ascoli Bartoli T, Castilletti C, Lalle E, et al. 2020. Pharmacokinetics of remdesivir and GS-441524 in two critically ill patients who recovered from COVID-19. J Antimicrob Chemother. 75(10):2977–2980. doi: 10.1093/jac/dkaa239.
   PubMed Web of Science ®Google Scholar
• Tempestilli M, Stazi GV, Maffongelli G, Marini MC, Ascoli Bartoli T, Ippolito G, Nicastri E, Marchioni L, Agrati C. 2021. Plasma concentrations of remdesivir metabolite in a critical COVID-19 patient needing continuous venovenous haemodialysis. Eur J Clin Pharmacol. 77(10):1583–1585. doi: 10.1007/s00228-021-03128-7.
   PubMed Web of Science ®Google Scholar
• VEKLURY Prescriber Information. 2022. Gilead Sciences I, Foster City, CA 94404, ed. Gilead Sciences.
   Google Scholar
• Warren TK, Jordan R, Lo MK, Ray AS, Mackman RL, Soloveva V, Siegel D, Perron M, Bannister R, Hui HC, et al. 2016. Therapeutic efficacy of the small molecule GS-5734 against Ebola virus in rhesus monkeys. Nature. 531(7594):381–385. doi: 10.1038/nature17180.
   PubMed Web of Science ®Google Scholar
• Weiss RC, Cox NR, Martinez ML. 1993. Evaluation of free or liposome-encapsulated ribavirin for antiviral therapy of experimentally induced feline infectious peritonitis. Res Vet Sci. 55(2):162–172. doi: 10.1016/0034-5288(93)90076-r.
   PubMed Web of Science ®Google Scholar
• Williamson BN, Feldmann F, Schwarz B, Meade-White K, Porter DP, Schulz J, van Doremalen N, Leighton I, Yinda CK, Pérez-Pérez L, et al. 2020. Clinical benefit of remdesivir in rhesus macaques infected with SARS-CoV-2. Nature. 585(7824):273–276. doi: 10.1038/s41586-020-2423-5.
   PubMed Web of Science ®Google Scholar
• Xie J, Wang Z. 2021. Can remdesivir and its parent nucleoside GS-441524 be potential oral drugs? An in vitro and in vivo DMPK assessment. Acta Pharm Sin B. 11(6):1607–1616. doi: 10.1016/j.apsb.2021.03.028.
   PubMed Web of Science ®Google Scholar
• Yan VC, Muller FL. 2021. Why remdesivir failed: preclinical assumptions overestimate the clinical efficacy of remdesivir for COVID-19 and Ebola. Antimicrob Agents Chemother. 65(10):e01117–01121. doi: 10.1128/AAC.01117-21.
   PubMed Web of Science ®Google Scholar
• Yates M-R, Katherine L. 2018. The evolution of nucleoside analogue antivirals: a review for chemists and non-chemists. Part 1: early structural modifications to the nucleoside scaffold. Antiviral Res. 154:66–86. doi: 10.1016/j.antiviral.2018.04.004.
   PubMed Web of Science ®Google Scholar