In vivo antiviral activity and pharmacokinetics of (-)-cis-5-fluoro-1- [2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine in woodchuck hepatitis virus- infected woodchucks

Antimicrobial Agents and Chemotherapy

Volumn 41, Issue 10, 1997, Pages 2076-2082

  Cullen, John M ^a   Smith, Sheila L ^b   Davis, Michelle G ^b   Dunn, Sandra E ^a   Botteron, Catherine ^a   Cecchi, Amanda ^a   Linsey, Deanna ^a   Linzey, David ^a   Frick, Lloyd ^b   Paff, Melanie T ^b   Goulding, Andrew ^b   Biron, Karen ^b  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

^b GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA POLYMERASE; EMTRICITABINE; VIRUS DNA;

ANIMAL HEPATITIS; ANIMAL MODEL; ANIMAL TISSUE; ANTIVIRAL ACTIVITY; ARTICLE; DRUG CLEARANCE; DRUG EFFICACY; DRUG HALF LIFE; DRUG METABOLISM; ENANTIOMER; INTRAPERITONEAL DRUG ADMINISTRATION; NONHUMAN; PRIORITY JOURNAL; WOODCHUCK;

EID: 0030754358     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.41.10.2076     Document Type: Article

References (63)

1. Bartholomew, M. M., R. W. Jansen, L. J. Jeffers, K. R. Reddy, L. C. Johnson, H. Bunzendahl, L. D. Condreay, A. G. Tzakis, E. R. Schiff, and N. A. Brown. 1997. Hepatitis B virus resistance to lamivudine given for recurrent hepatitis B infection after orthotopic liver transplantation. Lancet 349:20-22.
2. Bassendine, M. F., R. G. Chadwick, J. Salmeron, U. Shipton, H. C. Thomas, and S. Sherlock. 1981. Adenine arabinoside therapy in HBSAg-positive chronic liver disease: a controlled study. Gastroenterology 80:1016-1022.
3. Beasley, R. P., L.-Y. Hwang, C.-C. Ling, and C.-S. Chien. 1981. Hepatocellular carcinoma and hepatitis B virus. Lancet ii:1129-1133.
4. Carreno, V., J. C. Porres, I. Mora, J. Gutiez, J. A. Quiroga, S. Ramon-y-Cajal. H. Oliva, C. Compernolle, and J. Bartolome. 1987. A controlled study of treatment with recombinant interferon alpha in chronic hepatitis B virus infection: induction and maintenance schedules. Antiviral Res. 8:125-137.
5. Choi, W. B., L. J. Wilson, S. Yeola, D. C. Liotta, and R. F. Schinazi. 1991. In situ complexation directs the stereochemistry of N-glycosylation in the synthesis of oxothiolanyl and dioxolanyl nucleoside analogs. J. Am. Chem. Soc. 113:9377-9379.
6. Condreay, L. D., R. W. Jansen, T. F. Powdrill, L. C. Johnson, D. W. Selleseth, M. T. Paff, S. M. Daluge, G. R. Painter, P. A. Furman, M. N. Ellis, and D. R. Averett. 1994. Evaluation of the potent anti-hepatitis B virus agent (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl] Cytosine in a novel in vivo model. Antimicrob. Agents Chemother. 38:616-619.
7. Cote, P. J., R. E. Engle, C. A. Langer, A. Ponzetto, and J. L. Gerin. 1984. Antigenic analysis of woodchuck hepatitis virus surface antigen with site-specific radioimmunoassays. J. Virol. 49:701-708.
8. Cullen, J. M., and P. L. Marion. 1996. Non neoplastic liver disease associated with chronic ground squirrel hepatitis virus infection. Hepatology 23: 1324-1329.
9. Cullen, J. M., P. L. Marion, and J. E. Newbold. 1989. A sequential histologic and immunohistochemical study of duck hepatitis B virus infection in Pekin ducks. Vet. Pathol. 26:164-172.
10. Davis, M. G., J. E. Wilson, N. A. VanDraanen, W. H. Miller, G. A. Freeman, S. M. Daluge, F. L. Boyd, A. E. Aulabaugh, G. R. Painter, and L. R. Boone. 1996. DNA polymerase activity of hepatitis B virus particles: differential inhibition of L-enantiomers of nucleotide analogs. Antiviral Res. 30:133-145.
11. Davis, M. G. Unpublished data.
12. Doong, S.-L., C.-H. Tsai, R. F. Schinazi, D. C. Liotta, and Y.-C. Cheng. 1991. Inhibition of the replication of hepatitis B virus in vitro by 2′,3′-dideoxy-3′-thiacytidine and related analogues. Proc. Natl. Acad. Sci. USA 88:8495-8499.
13. Fourel, I., J. M. Cullen, J. Saputelli, C. E. Aldrich, P. Schaffer, D. R. Averett, J. Pugh, and W. S. Mason. 1994. Evidence that hepatocyte turnover is required for rapid clearance of duck hepatitis B virus during antiviral therapy of chronically infected ducks. J. Virol. 68:8321-8330.
14. Fourel, I., O. Hantz, K. A. Watanabe, C. Jacquet, B. Chomel, J. J. Fox, and C. Trepo. 1990. Inhibitory effects of 2′-fluorinated arabinosyl-pyrimidine nucleosides on woodchuck hepatitis virus replication in chronically infected woodchucks. Antimicrob. Agents Chemother. 34:473-475.
15. Fourel, I., O. Hantz, L. Cova, H. S. Allaudeen, and C. Trepo. 1987. Main properties of duck hepatitis B virus DNA polymerase: comparison with the human and woodchuck hepatitis B virus DNA polymerases. Antiviral Res. 8:189-199.
16. Frick, L. W., L. St. John, L. C. Taylor, G. R. Painter, P. A. Furman, D. C. Liotta, E. S. Furfine, and D. J. Nelson. 1993. Pharmacokinetics, oral bioavailability, and metabolic disposition in rats of (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl] cytosine, a nucleoside analog active against human immunodeficiency virus and hepatitis B virus. Antimicrob. Agents Chemother. 37:2285-2292.
17. Furman, P. A., M. Davis, D. C. Liotta, M. T. Paff, L. W. Frick, D. J. Nelson, R. E. Dornsife, J. A. Wurster, L. J. Wilson, F. A. Fyfe, J. V. Tuttle, W. H. Miller, L. D. Condreay, D. R. Avrett, R. Schinazi, and G. R. Painter. 1992. The anti-hepatitis B virus activities, cytotoxicities, and anabolic profiles of the (-) and (+) enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine. Anlimicrob. Agents Chemother. 36:2686-2692.
18. Galibert, F., T. N. Chen, and E. Mandart. 1982. Nucleotide sequence of a cloned woodchuck hepatitis virus genome: comparison with the hepatitis B virus sequence. J. Virol. 41:51-65.
19. Gerin, J. L., B. E. Korba, P. J. Cote, and B. C. Tennant. 1992. A preliminary report of a controlled study of thymosin alpha-1 in the woodchuck model of hepadnavirus infection, p. 121-123. In T. M. Block, D. Jung Kind, R. L. Crowell, M. Denison, and L. R. Walsh (ed.), innovations in antiviral development and the detection of virus infections. Plenum Press, New York, N.Y.
20. Gust, I. D., C. J. Burell, A. G. Coulepis, W. S. Robinson, and A. I. Zuckerman. 1986. Taxonomic classification of human hepatitis B virus. Intervirology 25:14-29.
21. Habteyesus, A., A. Nordenskjold, C. Bohman, and S. Eriksson. 1991. Deoxynucleoside phosphorylating enzymes in monkey and human tissues show great similarities while mouse deoxycytidine kinase has a different substrate specificity. Biochem. Pharmacol. 42:1829-1836.
22. Hantz, O., H. S. Allaudeen, T. Ooka, E. De Clercq, and C. Trepo. 1984. Inhibition of human and woodchuck hepatitis virus DNA polymerase by the triphosphates of acyclovir, 1-(2′-deoxy-2′-fluoro-β-D-arabinofuranosyl)-5-iodocytosine and E-5-(2-bromovinyl)-2′-deoxyuridine. Antiviral Res. 4:187-199.
23. Hantz, O., T. Ooka, I. Vitvitski, C. Pichoud, and C. Trepo. 1984. Comparison of properties of woodchuck hepatitis virus and human hepatitis B virus endogenous DNA polymerases. Antimicrob. Agents Chemother. 25:242-246.
24. Kaplan, P. M., R. L. Greenman, J. L. Gerin, R. H. Purcell, and W. S. Robinson. 1973. DNA polymerase associated with human hepatitis B antigen. J. Virol. 12:995-1005.
25. Kassianides, C., J. H. Hoofnagle, R. H. Miller, E. Doo, H. Ford, S. Broder, and H. Mitsuya. 1989. Inhibition of duck hepatitis B virus replication by 2′,3′-dideoxycytidine. Gastroenterology 97:1275-1280.
26. Korba, B. E., F. Wells, B. C. Tennant, G. H. Yoakum, R. H. Purcell, and J. L. Gerin, 1986. Hepadnavirus infection of peripheral blood lymphocytes in vivo: woodchuck and chimpanzee models of viral hepatitis. J. Virol. 58:1-8.
27. Korba, B. E., F. Wells, B. C. Tennant, P. J. Cole, and J. L. Gerin. 1987. Lymphoid cells in the spleens of woodchuck hepatitis virus-infected woodchucks are a site of active viral replication. J. Virol. 61:1318-1324.
28. Lofgren, B., E. Nordenfelt, and B. Oberg. 1989. Inhibition of RNA-and DNA-dependent duck hepatitis B virus DNA polymerase activity by nucleoside and pyrophosphate analogs. Antiviral Res. 12:301-310.
29. Mason, W. S., and J. M. Taylor. 1989. Experimental systems for the study of hepadnavirus and hepatitis delta virus infections. Hepatology 9:635-645.
30. Mason, W. S., J. M. Cullen, J. Saputelli, T.-T. Wu, C. Liu, W. T. London, E. Lustbader, P. Schaffer, A. P. O'Connell, I. Fourel, C. E. Aldrich, and A. R. Jilbert. 1994. Characterization of the antiviral effects of 2′ carbodeoxyguanosine in ducks chronically infected with duck hepatitis B virus. Hepatology 19:398-411.
31. Maynard, J. E. 1990. Hepatitis B: global importance and need for control. Vaccine 8(Suppl.):185-205.
32. McKenzie, R., M. W. Fried, R. Sallie, H. Conjeevaram, A. M. DiBisceglie, Y. Park, B. Savarese, D. Kleiner, M. Tsokos, C. Luciano, et al. 1995. Hepatic failure and lactic acidosis due to fialuridine (FIAU), an investigational nucleoside analogue for chronic hepatitis B. N. Engl. J. Med. 333:1099-1105.
33. Newbold, J. E. 1997. A heterogeneous response for a mammalian hepadna-virus infection to acyclovir: drug-arrested intermediates of minus-strand viral DNA synthesis are enveloped and secreted from infected cells as virus-like particles. J. Med. Virol. 51:6-16.
34. Newbold, J. E. Unpublished data.
35. Paff, M., D. R. Averett, K. L. Prus, W. H. Miller, and D. J. Nelson. 1994. Intracellular metabolism of (-)-and (+)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine in HepG2 derivative 2.2.15 (subclone P5A) cells. Antimicrob. Agents Chemother. 38:1230-1238.
36. Paff, M. Unpublished data.
37. Perrillo, R. P., E. R. Schiff, G. L. Davis, H. C. Bodenheimer, Jr., K. Lindsay, J. Payne, J. L. Dienstag, C. O'Brien, C. Tamburro, I. M. Jacobson, R. Sampliner, D. Feit, J. Lefkowitch, M. Kuhns, C. Meschievitz, B. Sanghvi, J. Albrecht, A. Gibas, and the Hepatitis Interventional Therapy Group. 1990. A randomized, controlled trial of Interferon alfa-2b alone and after prednisone withdrawal for the treatment of chronic hepatitis B. N. Engl. J. Med. 323:295-301.
38. Pollard, J. H. 1977. A handbook of numerical and statistical techniques, p. 2434. Cambridge University Press, Cambridge, United Kingdom.
39. Ponzetto, A., P. J. Cote, E. C. Ford, R. H. Purcell, and J. L. Gerin. 1984. Core antigen and antibody in woodchucks after infection with woodchuck hepatitis virus. J. Virol. 52:70-76.
40. Popper, H., L. Roth, R. H. Purcell, B. C. Tennant, and J. L. Gerin. 1987. Hepatocarcinogenicity of the woodchuck hepatitis virus. Proc. Natl. Acad. Sci. USA 84:866-870.
41. Rajagopalan, P., F. D. Boudinot, C. K. Chu, B. C. Tennant, B. H. Baldwin, and R. F. Schinazi. 1996. Pharmacokinetics of (-)-2′-3′-dideoxy-3′-thiacytidine in woodchucks. Antimicrob. Agents Chemother. 40:642-645.
42. Renault, P. F., and J. H. Hoofnagle. 1989. Side effects of interferon. Semin. Liver Dis. 9:273-277.
43. Roggendorf, M., and T. K. Tolle. 1995. The woodchuck: an animal model for hepatitis B virus infection in man. Intervirology 38:100-112.
44. Roth, L., J. M. King, W. E. Hornbuckle, H. J. Harvey, and B. C. Tennant. 1985. Chronic hepatitis and hepatocellular carcinoma associated with persistent woodchuck hepatitis virus infection. Vet. Pathol. 22:338-343.
45. SAS Institute, Inc. 1990. SAS language reference, version 6, 1st ed. SAS Institute, Inc., Cary, N.C. 1990.
46. SAS Institute, Inc. 1992. SAS technical report P-229. Software Changes and Enhancements for SAS/STAT, version 6.07, p. 369-405. SAS Institute, Inc., Cary, N.C.
47. SAS Institute, Inc. 1989. SAS/STAT User's Guide, version 6, vol. 2, 4th ed., p. 891. SAS Institute, Inc., Cary, N.C.
48. Schalm, S. W., H. C. Thomas, and S. J. Hadziyannis. 1990. Chronic hepatitis B, p. 443-162. In H. Popper and F. Schaffner (ed.), Progress in liver diseases. The W. B. Saunders Co., Philadelphia, Pa.
49. Schinazi, R. F., A. McMillan, D. Cannon, R. Mathis, R. M. Lloyd, A. Peck, J.-P. Sommadossi, M. St. Clair, J. Wilson, P. A. Furman, G. Painter, W.-B. Choi, and D. C. Liotta. 1992. Selective inhibition of human immunodeficiency viruses by racemates and enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine. Antimicrob. Agents Chemother. 36: 2423-2431.
50. Schinazi, R. F., R. M. Lloyd, Jr., M. H. Nguyen, D. L. Cannon, A. McMillan, N. Ilksoy, C. K. Chu, D. C. Liotta, H. Z. Bazmi, and J. W. Mellors. 1993. Characterization of human immunodeficiency viruses resistant to oxathiolane-cytosine nucleosides. Antimicrob Agents Chemother. 37:875-881.
51. Scullard, G. H., L. L. Andres, H. B. Greenberg, J. L. Smith, V. K. Sawhney, E. A. Neal, A. S. Mahal, H. Popper, T. C. Merigan, W. S. Robinson, and P. B. Gregory. 1981. Antiviral treatment of chronic hepatitis B virus infection: improvement in liver disease with interferon and adenine arabinoside. Hepatology 1:228-232.
52. Shaw, T., P. Amor, G. Civitico, M. Boyd, and S. Locarnini. 1994. In vitro antiviral activity of penciclovir, a novel purine nucleoside, against duck hepatitis B virus. Antimicrob. Agents Chemother. 38:719-723.
53. Sherker, A. H., K. Hirota, M. Omata, and K. Okuda. 1986. Foscarnet decreases serum and liver duck hepatitis B virus DNA in chronically infected ducks. Gastroenterology 91:818-824.
54. Smee, D. F., S. S. Knight, A. E. Duke, W. S. Robinson, T. R. Matthews, and P. L. Marion. 1985. Activities of arabinosyladenine monophosphate and 9-(1,3-dihydroxy-2-propoxymethyl)guanine against ground squirrel hepatitis virus in vivo as determined by reduction in serum virion-associated DNA polymerase. Antimicrob. Agents Chemother. 27:277-279.
55. Tencza, M. G., and J. E. Newbold. 1997. Heterogeneous response for a mammalian hepadnavirus infection to acyclovir: drug arrested intermediates of minus strand viral DNA synthesis are enveloped and secreted from infected cells as virion-like particles. J. Med. Virol. 51:6-16.
56. Staschke, K. A., J. M. Colacino, T. E. Mabry, and C. D. Jones. 1994. The in vitro anti-hepatitis B virus activity of FIAU [1-(2′-deoxy-2′-fluoro-1-beta-D-arabinofuranosyl-5-iodo)uracil] is selective, reversible and determined, at least in part, by the host cell. Antiviral Res. 23:45-61.
57. Suzuki, S., B. Lee, W. Luo, D. Tovell, M. J. Robins, and D. L. J. Tyrrell. 1988. Inhibition of duck hepatitis B virus replication by purine 2′,3′-dideoxynucleosides. Biochem. Biophys. Res. Commun. 156:1144-1151.
58. Tisdale, M., S. D. Kemp, N. R. Parry, and B. A. Larder. 1993. Rapid in vitro selection of human immunodeficiency virus type 1 resistant to 3′-thiacytidine inhibitors due to a mutation in the YMDD region of reverse transcriptase. Proc. Natl. Acad. Sci. USA 90:5653-5656.
59. Venkateswaran, P. S., I. Millman, and B. S. Blumberg. 1987. Effects of an extract from Phyllanthus niruri on hepatitis B and woodchuck hepatitis viruses: in vitro and in vivo studies. Proc. Natl. Acad. Sci. USA 84:274-278.
60. Weissberg, J. I., L. L. Andres, and C. I. Smith. 1984. Survival in chronic hepatitis B: an analysis of 379 patients. Ann. Intern. Med. 101:613-616.
61. Westfall, P. H., and S. S. Young. 1993. Resampling based multiple testing, p. 112-121. John Wiley & Sons, Inc., New York, N.Y.
62. Winer, B. J. 1971. Statistical principles in experimental design. 2nd ed., p. 518-538. McGraw-Hill Book Co., New York, N.Y.
63. Yarchoan, R., R. V. Thomas, J.-P. Allain, N. McAtee, R. Dubinsky, H. Mitsuya, T. J. Lawley, B. Safai, C. E. Meyers, C. F. Perno, R. W. Kiecker, R. J. Wills, M. A. Fischi, M. C. McNeeley, J. M. Pluda, M. Leuther, J. M. Collins, and S. Broder. 1988. Phase I studies of 2′-3′-dideoxycytidine in severe human immunodeficiency virus infection as a single agent and alternating with zidovudinc (AZT). Lancet i:76-81.