Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 40, 2010 - Issue 12
222
Views
16
CrossRef citations to date
0
Altmetric
Animal Pharmacokinetics and Metabolism

The metabolism and disposition of a potent inhibitor of hepatitis C virus NS3/4A protease

, , , , , , , , , , , & show all
Pages 826-839 | Received 14 May 2010, Accepted 24 Aug 2010, Published online: 07 Oct 2010

References

  • Benet LZ, Galeazzi RL. (1979). Noncompartmental determination of the steady-state volume of distribution. Journal of Pharmaceutical Sciences 68:1071–1074.
  • De Francesco R, Carfi A. (2007). Advances in the development of new therapeutic agents targeting the NS3-4A serine protease or the NS5B RNA-dependent RNA polymerase of the hepatitis C virus. Adv Drug Delivery Rev 59:1242–1262.
  • Di Bisceglie AM, Hoofnagle JH. (2002). Optimal therapy of hepatitis C. Hepatology 36:S121–S127.
  • Evers R, Kool M, Van Deemter L, Janssen H, Calafat J, Oomen LCJM, Paulusma CC, Oude Elferink RPJ, Baas F, Schinkel AH, Borst P. (1998). Drug export activity of the human canalicular multispecific organic anion transporter in polarized kidney MDCK cells expressing cMOAT (MRP2) cDNA. J Clin Invest 101:1310–1319.
  • Feld JJ, Hoofnagle JH. (2005). Mechanism of action of interferon and ribavirin in treatment of hepatitis C. Nature 436:967–972.
  • Fried MW, Shiffman ML, Reddy KR, Smith C, Marinos G, Goncales FL, Haussinger D, Diago M, Carosi G, Dhumeaux D, Craxi A, Lin A, Hoffman J, Yu J. (2002). Peg interferon alfa-2a plus ribavirin for chronic hepatitis C virus infection. N Engl J Med 347:975–982.
  • Gale M, Foy EM. (2005). Evasion of intracellular host defence by hepatitis C virus. Nature 436:939–945.
  • Hadziyannis SJ, Sette H, Morgan TR, Balan V, Diago M, Marcellin P; PEGASYS International Study Group. (2004). Peg interferon-alpha 2a and ribavirin combination therapy in chronic hepatitis C: a randomized study of treatment duration and ribavirin dose. Ann Intern Med 140:346–355.
  • 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.
  • Leuthold S, Hagenbuch B, Mohebbi N, Wagner CA, Meier PJ, Stieger B. (2009). Mechanisms of pH-gradient driven transport mediated by organic anion polypeptide transporters. Am J Physiol Cell Physiol 296:570–582.
  • Lin C, Kwong AD, Perni RB. (2006). Discovery and development of VX-950, a novel, covalent, and reversible inhibitor of hepatitis C virus NS3-4A serine protease. Infect Dis Drug Target 6:3–16.
  • Liverton NJ, Carroll SS, Di Muzio J, Fandozzi C, Graham DJ, Hazuda D, Holloway MK, Ludmerer SW, McCauley JA, McIntyre CJ, Olsen DB, Rudd MY, Stahlhut M, Vacca JP. (2010). MK-7009: a potent and selective inhibitor of hepatitis C virus NS3/4A protease. Antimicrob Agents Chemother 54:305–311.
  • Liverton NJ, Holloway MK, McCauley JA, Rudd MT, Butcher JW, Carroll SS, DiMuzio J, Fandozzi C, Gilbert KF, Mao SS, McIntyre CJ, Nguyen KT, Romano JJ, Stahlhut M, Wan BL, Olsen DB, Vacca JP. (2008). Molecular modeling based approach to potent P2–P4 macrocyclic inhibitors of hepatitis C NS3/4a protease. J Am Chem Soc 130:4607–4609.
  • Llinàs-Brunet M, Bailey MD, Bolger G, Brochu C, Faucher AM, Ferland JM, Garneau M, Ghiro E, Gorys V, Grand-Maître C, Halmos T, Lapeyre-Paquette N, Liard F, Poirier M, Rhéaume M, Tsantrizos YS, Lamarre D. (2004). Structure–activity study on a novel series of macrocyclic inhibitors of the hepatitis C virus NS3 protease leading to the discovery of BILN 2061. J Med Chem 47:1605–1608.
  • Mahagita C, Grassi SM, Piyachaturawat P, Ballatori N. 2007. Human organic anion transporter 1B1 (OATP1B1/OATP-C) and 1B3 (OATP1B3/OATP-8) function as bidirectional cariers and do not mediate GSH-bile acid co-transport. Am J Physiol Gastrointest Liver Physiol 293: G271–G278.
  • Manns MP, McHutchison JG, Gordon SC, Rustgi VK, Shiffman M, Reindollar R, Goodman ZD, Koury K, Ling M, Albrecht JK. (2001). Peg interferon alfa-2b plus ribavirin compared with interferon alfa-2b plus ribavirin for initial treatment of chronic hepatitis C: a randomized trial. Lancet 358:958–965.
  • Manns MP, Wedemeyer H, Cornberg M. (2006). Treating viral hepatitis C: efficacy, side effects, and complications. Gut 55:1350–1359.
  • McCauley JA, McIntyre CJ, Rudd MT, Nguyen KT, Romano JJ, Butcher JW, Gilbert K F, Bush KJ, Holloway MK, Swestoc J, Wan B, Carroll SS, DiMuzio JM, Graham DJ, Ludmerer SW, Mao S, Stahlhut M, Fandozzi C, Trainor N, Olsen DB, Vacca JP, Liverton NJ. 2010. Discovery of Vaniprevir (MK-7009), a macrocyclic hepatitis C NS3/4a protease inhibitor. J Med Chem 53:2443–2463.
  • McCauley JA, Rudd MT, Nguyen KT, McIntyre CJ, Romano JJ, Bush KJ, Varga SL, Ross CW, Carroll SS, DiMuzio J, Stahlhut MW, Olsen DB, Lyle TA, Vacca JP, Liverton NJ. (2008). Bismacrocyclic inhibitors of hepatitis C NS3/4a protease. Angew Chem Int Ed 47:9104–9107.
  • McHutchison JG, Gordon SC, Schiff ER, Shiffman ML, Lee WM, Rusti VK, Goodman ZD, Ling MH, Cort S, Albrecht JK. (1998). Interferon alfa-2b alone or in combination with ribavirin as initial treatment for chronic hepatitis C. N Engl J Med 339:1485–1492.
  • Meier-Abt F, Mokrab Y, Mizuguchi K. 2005. Organic anion transporting polypeptides of the OATP/SLCO superfamily: identification of new members in nonmammalian species, comparative modeling and a potential transport mode. J Membr Biol 208: 213–227.
  • Niemi M. (2007). Role of OATP transporters in the disposition of drugs. Pharmacogenomics 8:787–802.
  • 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.
  • Prongay AJ, Guo Z, Yao N, Pichardo J, Fischmann T, Strickland C, Myers J, Weber PC, Beyer BM, Ingram R, Hong Z, Prosise WW, Ramanathan L, Taremi SS, Yarosh-Tomaine T, Zhang R, Senior M, Yang RS, Malcolm B, Arasappan A, Bennett F, Bogen SL, Chen K, Jao E, Liu YT, Lovey RG, Saksena AK, Venkatraman S, Girijavallabhan V, Njoroge FG, Madison V. (2007). Discovery of the HCV NS3/4A protease inhibitor (1R,5S)-N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[2(S)-[[[(1,1dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2(S)-carboxamide (SCH 503034). Key steps in structure-based optimization. J Med Chem 50:2310–2318.
  • Rustgi VK. (2007). The epidemiology of hepatitis C infection in the United States. J Gastroenterol 42:513–521.
  • Shepard CW, Finelli L, Alter MJ. (2005). Global epidemiology of hepatitis C virus infection. Lancet Infect Dis 5:558–567.
  • Simmonds P, Bukh J, Combet C, Deléage G, Enomoto N, Feinstone S, Halfon P, Inchauspé G, Kuiken C, Maertens G, Mizokami M, Murphy D, Okamoto H, Pawlotsky J, Penin F, Sablon E, Shin IT, Stuyver L, Thiel H, Viazov S, Weiner A, Widell A. (2005). Consensus proposals for a unified system of nomenclature of hepatitis C virus genotypes. Hepatology 42:962–973.
  • Strader DB, Wright T, Thomas DL, Seeffm LB. (2004). Diagnosis, management, and treatment of hepatitis C. Hepatology 39:1147–1171.
  • Tsantrizos YS. (2008). Peptidomimetic therapeutic agents targeting the protease enzyme of the human immunodeficiency virus and hepatitis C virus. Acc Chem Res 41:1252–1263.
  • Venkatraman S, Bogen SL, Arasappan A, Bennett F, Chen K, Jao E, Liu YT, Lovey R, Hendrata S, Huang Y, Pan W, Parekh T, Pinto P, Popov V, Pike R, Ruan S, Santhanam B, Vibulbhan B, Wu W, Yang W, Kong J, Liang X, Wong J, Liu R, Butkiewicz N, Chase R, Hart A, Agrawal S, Ingravallo P, Pichardo J, Kong R, Baroudy B, Malcolm B, Guo Z, Prongay A, Madison V, Broske L, Cui X, Cheng KC, Hsieh Y, Brisson JM, Prelusky D, Korfmacher W, White R, Bogdanowich-Knipp S, Pavlovsky A, Bradley P, Saksena AK, Ganguly A, Piwinski J, Girijavallabhan V, Njoroge FG. (2006). Discovery of (1R,5S)-N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[2(S)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2(S)-carboxamide (SCH 503034), a selective, potent, orally bioavailable hepatitis C virus NS3 protease inhibitor: a potential therapeutic agent for the treatment of hepatitis C infection. J Med Chem 49:6074–6086.
  • Wasley A, Alter MJ. (2000). Epidemiology of hepatitis C: geographic differences and temporal trends. Semin Liver Dis 20:1–16.
  • World Health Organization (WHO). (1999). Initiative for vaccine research. Hepatitis C. <http://www.who.int/vaccine_research/diseases/viral_cancers/en/index2.html>

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.