The delivery of arbidol by salt engineering: synthesis, physicochemical properties and pharmacokinetics

References

• Blaising J, Polyak SJ, Pecheur EI. Arbidol as a broad-spectrum antiviral: an update. Antiviral Res 2014;107:84–94.
   PubMed Web of Science ®Google Scholar
• Brooks MJ, Burtseva EI, Ellery PJ, et al. Antiviral activity of arbidol, a broad-spectrum drug for use against respiratory viruses, varies according to test conditions. J Med Virol 2012;84:170–81.
   PubMed Web of Science ®Google Scholar
• Shi L, Xiong H, He J, et al. Antiviral activity of arbidol against influenza A virus, respiratory syncytial virus, rhinovirus, coxsackie virus and adenovirus in vitro and in vivo. Arch Virol 2007;152:1447–55.
   PubMed Web of Science ®Google Scholar
• Pecheur EI, Lavillette D, Alcaras F, et al. Biochemical mechanism of hepatitis C virus inhibition by the broad-spectrum antiviral arbidol. Biochemistry 2007;46:6050–9.
   PubMed Web of Science ®Google Scholar
• Delogu I, Pastorino B, Baronti C, et al. In vitro antiviral activity of arbidol against Chikungunya virus and characteristics of a selected resistant mutant. Antiviral Res 2011;90:99–107.
   PubMed Web of Science ®Google Scholar
• Deng HY, Luo F, Shi LQ, et al. Efficacy of arbidol on lethal hantaan virus infections in suckling mice and in vitro. Acta Pharmacologica Sinica 2009;30:1015–24.
   PubMed Web of Science ®Google Scholar
• Leneva IA, Russell RJ, Boriskin YS, et al. Characteristics of arbidol-resistant mutants of influenza virus: implications for the mechanism of anti-influenza action of arbidol. Antiviral Res 2009;81:132–40.
   PubMed Web of Science ®Google Scholar
• Perfetto B, Filosa R, De Gregorio V, et al. In vitro antiviral and immunomodulatory activity of arbidol and structurally related derivatives in herpes simplex virus type 1-infected human keratinocytes (HaCat). J Med Microbiol 2014;63:1474–83.
   PubMed Web of Science ®Google Scholar
• Li S, Doyle P, Metz S, et al. Effect of chloride ion on dissolution of different salt forms of haloperidol, a model basic drug. J Pharm Sci 2005;94:2224–31.
   PubMed Web of Science ®Google Scholar
• Li S, Wong S, Sethia S, et al. Investigation of solubility and dissolution of a free base and two different salt forms as a function of pH. Pharm Res 2005;22:628–35.
   PubMed Web of Science ®Google Scholar
• Eropkin MY, Solovskii MV, Smirnova MY, et al. Synthesis and biological activity of water-soluble polymer complexes of arbidol. Pharm Chem J 2009;43:563–7.
   Web of Science ®Google Scholar
• Babkin VA, Kiselev OI. Method for preparing antiviral water-soluble polymer complexes of Arbidol. 2013:RU 2475255C1.
   Google Scholar
• Surov AO, Manin AN, Churakov AV, et al. New solid forms of the antiviral drug arbidol: crystal structures, thermodynamic stability, and solubility. Mol Pharm 2015;12:4154–65.
   PubMed Web of Science ®Google Scholar
• Orola L, Sarcevica I, Kons A, et al. Conformation of the umifenovir cation in the molecular and crystal structures of four carboxylic acid salts. J Mol Struct 2014;1056–57:63–9.
   Web of Science ®Google Scholar
• Manin A, Surov A, Churakov A, et al. Crystal structures, thermal analysis, and dissolution behavior of new solid forms of the antiviral drug arbidol with dicarboxylic acids. Crystals 2015;5:650.
   Web of Science ®Google Scholar
• Elder DP, Holm R, Diego HL. Use of pharmaceutical salts and cocrystals to address the issue of poor solubility. Int J Pharm 2013;453:88–100.
   PubMed Web of Science ®Google Scholar
• Paulekuhn GS, Dressman JB, Saal C. Trends in active pharmaceutical ingredient salt selection based on analysis of the Orange Book database. J Med Chem 2007;50:6665–72.
   PubMed Web of Science ®Google Scholar
• Saal C, Becker A. Pharmaceutical salts: a summary on doses of salt formers from the Orange Book. Eur J Pharm Sci 2013;49:614–23.
   PubMed Web of Science ®Google Scholar
• Serajuddin AT. Salt formation to improve drug solubility. Adv Drug Deliv Rev 2007;59:603–16.
   PubMed Web of Science ®Google Scholar
• Elder DP, Delaney E, Teasdale A, et al. The utility of sulfonate salts in drug development. J Pharm Sci 2010;99:2948–61.
   PubMed Web of Science ®Google Scholar
• Adiki SK. International conference on hormonization (ICH) harmonized tripartite guideline. Validation of analytical procedures: text and methodology. 2005;Q2:1–13.
   Google Scholar
• Guerrieri P, Rumondor AC, Li T, et al. Analysis of relationships between solid-state properties, counterion, and developability of pharmaceutical salts. AAPS PharmSciTech 2010;11:1212–22.
   PubMed Web of Science ®Google Scholar
• Korn C, Balbach S. Compound selection for development - is salt formation the ultimate answer? Experiences with an extended concept of the 100mg approach. Eur J Pharm Sci 2014;57:257–63.
   PubMed Web of Science ®Google Scholar
• Childs SL, Stahly GP, Park A. The salt-cocrystal continuum: the influence of crystal structure on ionization state. Mol Pharm 2007;4:323–38.
   PubMed Web of Science ®Google Scholar
• Black SN, Collier EA, Davey RJ, et al. Structure, solubility, screening, and synthesis of molecular salts. J Pharm Sci 2007;96:1053–68.
   PubMed Web of Science ®Google Scholar
• Berendsen BJ, Wegh RS, Essers ML, et al. Quantitative trace analysis of a broad range of antiviral drugs in poultry muscle using column-switch liquid chromatography coupled to tandem mass spectrometry. Anal Bioanal Chem 2012;402:1611–23.
   PubMed Web of Science ®Google Scholar
• Rahman Z, Zidan AS, Samy R, et al. Improvement of physicochemical properties of an antiepileptic drug by salt engineering. AAPS PharmSciTech 2012;13:793–801.
   PubMed Web of Science ®Google Scholar
• Cheney ML, Shan N, Healey ER, et al. Effects of crystal form on solubility and pharmacokinetics: a crystal engineering case study of lamotrigine. Cryst Growth Des 2010;10:394–405.
   Web of Science ®Google Scholar
• Stahl P, Nakano M. Handbook of pharmaceutical salts: properties, selection, and use. New York: Wiley-VCH; 2002; 83–116.
   Google Scholar
• Liu J. Biopharmaceutics and pharmacokinetics. Beijing, PR China: Prentice-Hall People's Medical; 2011:61–2.
   Google Scholar