Cross-species absorption, metabolism, distribution and pharmacokinetics of BI 201335, a potent HCV genotype 1 NS3/4A protease inhibitor

References

• Bachmann K, Pardoe D, White D. (1996). Scaling basic toxicokinetic parameters from rat to man. Environ Health Perspect 104:400–407.
   PubMed Web of Science ®Google Scholar
• Balfour HHJr. (1999). Antiviral drugs. N Engl J Med 340:1255–1268.
   PubMed Web of Science ®Google Scholar
• Bartenschlager R, Lohmann V, Wilkinson T, Koch JO. (1995). Complex formation between the NS3 serine-type proteinase of the hepatitis C virus and NS4A and its importance for polyprotein maturation. J Virol 69:7519–7528.
   PubMedGoogle Scholar
• Becker S, Fisher A, Flexner C, Gerber JG, Haubrich R, Kashuba AD, Luber AD, Piscitelli SC. (2001). Pharmacokinetic parameters of protease inhibitors and the Cmin/IC50 ratio: Call for consensus. J Acquir Immune Defic Syndr 27:210–211.
   PubMedGoogle Scholar
• Cheng KC, Li C, Liu T, Wang G, Hsieh Y, Pavlosky A, Broske L, Prelusky D, Liu R, White RE, Uss AS, Gupta S, Njoroge FG. (2009). Use of pre-clinical in vitro and in vivo pharmacokinetics for the selection of a potent hepatitis C virus protease inhibitor, boceprevir, for clinical development. Lett Drug Des Disc 6:312–318.
   Google Scholar
• De Clercq E. (2007). The design of drugs for HIV and HCV. Nat Rev Drug Discov 6:1001–1018.
   PubMed Web of Science ®Google Scholar
• Food and Drug Administration. (2006) Guidance for industry: Antiviral product development-conducting and submitting virology studies to the agency. [Online] Available at: http://www.fda.gov/OHRMS/DOCKETS/98fr/05d-0183-gdl0002-01.pdf. Accessed on 16 August 2010.
   Google Scholar
• Fagerholm U. (2007). Prediction of human pharmacokinetics–improving microsome-based predictions of hepatic metabolic clearance. J Pharm Pharmacol 59:1427–1431.
   PubMed Web of Science ®Google Scholar
• Gallinari P, Brennan D, Nardi C, Brunetti M, Tomei L, Steinkühler C, De Francesco R. (1998). Multiple enzymatic activities associated with recombinant NS3 protein of hepatitis C virus. J Virol 72:6758–6769.
   PubMed Web of Science ®Google Scholar
• Gibaldi M, Perrier D. (1982) Pharmacokinetics. New York: Marcel Dekker.
   Google Scholar
• Hinrichsen H, Benhamou Y, Wedemeyer H, Reiser M, Sentjens RE, Calleja JL, Forns X, Erhardt A, Crönlein J, Chaves RL, Yong CL, Nehmiz G, Steinmann GG. (2004). Short-term antiviral efficacy of BILN 2061, a hepatitis C virus serine protease inhibitor, in hepatitis C genotype 1 patients. Gastroenterology 127:1347–1355.
   PubMed Web of Science ®Google Scholar
• Hosea NA, Collard WT, Cole S, Maurer TS, Fang RX, Jones H, Kakar SM, Nakai Y, Smith BJ, Webster R, Beaumont K. (2009). Prediction of human pharmacokinetics from preclinical information: Comparative accuracy of quantitative prediction approaches. J Clin Pharmacol 49:513–533.
   PubMed Web of Science ®Google Scholar
• Kempf DJ, Klein C, Chen HJ, Klein LL, Yeung C, Randolph JT, Lau YY, Chovan LE, Guan Z, Hernandez L, Turner TM, Dandliker PJ, Marsh KC. (2007). Pharmacokinetic enhancement of the hepatitis C virus protease inhibitors VX-950 and SCH 503034 by co-dosing with ritonavir. Antivir Chem Chemother 18:163–167.
   PubMedGoogle Scholar
• Kim JL, Morgenstern KA, Lin C, Fox T, Dwyer MD, Landro JA, Chambers SP, Markland W, Lepre CA, O’Malley ET, Harbeson SL, Rice CM, Murcko MA, Caron PR, Thomson JA. (1996). Crystal structure of the hepatitis C virus NS3 protease domain complexed with a synthetic NS4A cofactor peptide. Cell 87:343–355.
   PubMed Web of Science ®Google Scholar
• Kronenberger B, Zeuzem S. (2009). Current and future treatment options for HCV. Ann Hepatol 8:103–112.
   PubMedGoogle Scholar
• Lamarre D, Anderson PC, Bailey M, Beaulieu P, Bolger G, Bonneau P, Bös M, Cameron DR, Cartier M, Cordingley MG, Faucher AM, Goudreau N, Kawai SH, Kukolj G, Lagacé L, LaPlante SR, Narjes H, Poupart MA, Rancourt J, Sentjens RE, St George R, Simoneau B, Steinmann G, Thibeault D, Tsantrizos YS, Weldon SM, Yong CL, Llinàs-Brunet M. (2003). An NS3 protease inhibitor with antiviral effects in humans infected with hepatitis C virus. Nature 426:186–189.
   PubMed Web of Science ®Google Scholar
• Lange CM, Sarrazin C, Zeuzem S. (2010). Review article: Specifically targeted anti-viral therapy for hepatitis C - a new era in therapy. Aliment Pharmacol Ther 32:14–28.
   PubMed Web of Science ®Google Scholar
• Lavé T, Coassolo P, Reigner B. (1999). Prediction of hepatic metabolic clearance based on interspecies allometric scaling techniques and in vitro-in vivo correlations. Clin Pharmacokinet 36:211–231.
   PubMed Web of Science ®Google Scholar
• Llinàs-Brunet M, Bailey MD, Goudreau N, Bhardwaj PK, Bordeleau J, Bös M, Bousquet Y, Cordingley MG, Duan J, Forgione P, Garneau M, Ghiro E, Gorys V, Goulet S, Halmos T, Kawai SH, Naud J, Poupart MA, White PW. (2010). Discovery of a potent and selective noncovalent linear inhibitor of the hepatitis C virus NS3 protease (BI 201335). J Med Chem 53:6466–6476.
   PubMed Web of Science ®Google Scholar
• Love RA, Parge HE, Wickersham JA, Hostomsky Z, Habuka N, Moomaw EW, Adachi T, Hostomska Z. (1996). The crystal structure of hepatitis C virus NS3 proteinase reveals a trypsin-like fold and a structural zinc binding site. Cell 87:331–342.
   PubMed Web of Science ®Google Scholar
• Mahmood I. (2005) Interspecies Pharmacokinetic Scaling. Rockville, MD: Pine House Publishers.
   Google Scholar
• Manns MP, Bourlière M, Benhamou Y, Pol S, Bonacini M, Trepo C, Wright D, Berg T, Calleja JL, White PW, Stern JO, Steinmann G, Yong CL, Kukolj G, Scherer J, Boecher WO. (2010). Potency, safety and pharmacokinetics of the NS3/4A protease inhibitor BI201335 in patients with chronic HCV genotype-1 infection. J Hepatol:Published online Dec. 9, 2010. DOI: 10.1016/j.jhep.2010.08.040.
   Google Scholar
• Moradpour D, Penin F, Rice CM. (2007). Replication of hepatitis C virus. Nat Rev Microbiol 5:453–463.
   PubMed Web of Science ®Google Scholar
• Obach RS, Baxter JG, Liston TE, Silber BM, Jones BC, MacIntyre F, Rance DJ, Wastall P. (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
• Perni RB, Almquist SJ, Byrn RA, Chandorkar G, Chaturvedi PR, Courtney LF, Decker CJ, Dinehart K, Gates CA, Harbeson SL, Heiser A, Kalkeri G, Kolaczkowski E, Lin K, Luong YP, Rao BG, Taylor WP, Thomson JA, Tung RD, Wei Y, Kwong AD, Lin C. (2006). Preclinical profile of VX-950, a potent, selective, and orally bioavailable inhibitor of hepatitis C virus NS3-4A serine protease. Antimicrob Agents Chemother 50:899–909.
   PubMed Web of Science ®Google Scholar
• Pollack TM, McCoy C, Stead W. (2009). Clinically significant adverse events from a drug interaction between quetiapine and atazanavir-ritonavir in two patients. Pharmacotherapy 29:1386–1391.
   PubMed Web of Science ®Google Scholar
• Reiser M, Hinrichsen H, Benhamou Y, Reesink HW, Wedemeyer H, Avendano C, Riba N, Yong CL, Nehmiz G, Steinmann GG. (2005). Antiviral efficacy of NS3-serine protease inhibitor BILN-2061 in patients with chronic genotype 2 and 3 hepatitis C. Hepatology 41:832–835.
   PubMed Web of Science ®Google Scholar
• Sahin S, Benet LZ. (2008). The operational multiple dosing half-life: A key to defining drug accumulation in patients and to designing extended release dosage forms. Pharm Res 25:2869–2877.
   PubMed Web of Science ®Google Scholar
• Schmidt S, Barbour A, Sahre M, Rand KH, Derendorf H. (2008). PK/PD: New insights for antibacterial and antiviral applications. Curr Opin Pharmacol 8:549–556.
   PubMed Web of Science ®Google Scholar
• Stoltz JH, Stern JO, Huang Q, Seidler RW, Pack FD, Knight BL. (2011). A twenty-eight-day mechanistic time course study in the rhesus monkey with hepatitis C virus protease inhibitor BILN 2061. Toxicol Pathol 39:496–501.
   PubMedGoogle Scholar
• Vita M, Abdel-Rehim M, Nilsson C, Hassan Z, Skansen P, Wan H, Meurling L, Hassan M. (2005). Stability, pKa and plasma protein binding of roscovitine. J Chromatogr B Analyt Technol Biomed Life Sci 821:75–80.
   PubMed Web of Science ®Google Scholar
• White PW, Llinàs-Brunet M, Amad M, Bethell RC, Bolger G, Cordingley MG, Duan J, Garneau M, Lagacé L, Thibeault D, Kukolj G. (2010). Preclinical characterization of BI 201335, a C-terminal carboxylic acid inhibitor of the hepatitis C virus NS3-NS4A protease. Antimicrob Agents Chemother 54:4611–4618.
   PubMed Web of Science ®Google Scholar