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Chemical Compound Review

Clevudine     1-[(2S,3R,4S,5S)-3-fluoro-4- hydroxy-5...

Synonyms: Levovir, Revovir, L-FMAU, PubChem23138, CHEMBL458875, ...
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Disease relevance of Clevudine

  • We determined the frequency of integrated viral DNA in the livers of three woodchucks chronically infected with the woodchuck hepatitis virus before and during 30 weeks of therapy with the nucleoside analog L-FMAU [1-(2-fluoro-5-methyl-beta, L-arabinofuranosyl)uracil, clevudine] [1].
  • Median serum hepatitis B virus DNA reductions from baseline at week 12 were 0.20, 4.49, and 4.45 log10 copies/mL in the placebo, 30-mg clevudine, and 50-mg clevudine groups, respectively (P < .0001) [2].
  • A phase II dose-escalating trial of clevudine in patients with chronic hepatitis B [3].
  • Clevudine was well tolerated, with no dose-limiting toxicities [3].
  • The reduction in viremia was remarkably rapid at the higher doses of L-FMAU, with greater than 1,000-fold reductions in WHV-DNA serum levels observed after as little as 2 to 3 days of therapy [4].
  • We describe two cases of drug-induced myopathy during long-term treatment of chronic hepatitis B with clevudine [5].
  • Myopathy associated with clevudine is characterized by a weakness in proximal muscles of the lower extremities with elevated muscle enzymes and presumably caused by mitochondrial toxicities [6].

High impact information on Clevudine


Chemical compound and disease context of Clevudine


Biological context of Clevudine


Anatomical context of Clevudine


Associations of Clevudine with other chemical compounds


Gene context of Clevudine

  • Behavior of thymidylate kinase toward monophosphate metabolites and its role in the metabolism of 1-(2'-deoxy-2'-fluoro-beta-L-arabinofuranosyl)-5-methyluracil (Clevudine) and 2',3'-didehydro-2',3'-dideoxythymidine in cells [20].
  • L-FMAU was metabolized in the cells to its mono-, di-, and triphosphates, A dose-dependent inhibition of HBV DNA synthesis by L-FMAU triphosphate was observed in the DNA polymerase assays with isolated HBV particles, suggesting that the mode of action of this compound could involve viral polymerase [12].
  • Unique metabolism of a novel antiviral L-nucleoside analog, 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil: a substrate for both thymidine kinase and deoxycytidine kinase [21].
  • In vitro cytotoxicity in MT2, CEM, 2.2.15, and H1 cells was also assessed, and the results indicated high antiviral selectivities of L-FMAU in these cells [22].
  • With the introduction of new nucleoside/nucleotide analogs such as entacavir, clevudine, LFd4C,tenofovir, and immunomodulatory agents such as pegylated IFN, new treatment options, either alone or in combination, are being investigated to increase the response rate in treatment-naïve and treatment-experienced chronic hepatitis B patients [23].

Analytical, diagnostic and therapeutic context of Clevudine


  1. Residual integrated viral DNA after hepadnavirus clearance by nucleoside analog therapy. Summers, J., Mason, W.S. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  2. A 12-week clevudine therapy showed potent and durable antiviral activity in hbeag-positive chronic hepatitis B. Lee, H.S., Chung, Y.H., Lee, K., Byun, K.S., Paik, S.W., Han, J.Y., Yoo, K., Yoo, H.W., Lee, J.H., Yoo, B.C. Hepatology (2006) [Pubmed]
  3. A phase II dose-escalating trial of clevudine in patients with chronic hepatitis B. Marcellin, P., Mommeja-Marin, H., Sacks, S.L., Lau, G.K., Sereni, D., Bronowicki, J.P., Conway, B., Trepo, C., Blum, M.R., Yoo, B.C., Mondou, E., Sorbel, J., Snow, A., Rousseau, F., Lee, H.S. Hepatology (2004) [Pubmed]
  4. Antiviral activity of clevudine [L-FMAU, (1-(2-fluoro-5-methyl-beta, L-arabinofuranosyl) uracil)] against woodchuck hepatitis virus replication and gene expression in chronically infected woodchucks (Marmota monax). Peek, S.F., Cote, P.J., Jacob, J.R., Toshkov, I.A., Hornbuckle, W.E., Baldwin, B.H., Wells, F.V., Chu, C.K., Gerin, J.L., Tennant, B.C., Korba, B.E. Hepatology (2001) [Pubmed]
  5. Clevudine myopathy in patients with chronic hepatitis B. Kim, B.K., Oh, J., Kwon, S.Y., Choe, W.H., Ko, S.Y., Rhee, K.H., Seo, T.H., Lim, S.D., Lee, C.H. J. Hepatol. (2009) [Pubmed]
  6. Clinical, biochemical, and pathological characteristics of clevudine-associated myopathy. Tak, W.Y., Park, S.Y., Cho, C.M., Jung, M.K., Jeon, S.W., Kweon, Y.O., Park, J.Y., Sohn, Y.K. J. Hepatol. (2010) [Pubmed]
  7. Clevudine therapy with vaccine inhibits progression of chronic hepatitis and delays onset of hepatocellular carcinoma in chronic woodchuck hepatitis virus infection. Korba, B.E., Cote, P.J., Menne, S., Toshkov, I., Baldwin, B.H., Wells, F.V., Tennant, B.C., Gerin, J.L. Antivir. Ther. (Lond.) (2004) [Pubmed]
  8. Inhibitory activity of dioxolane purine analogs on wild-type and lamivudine-resistant mutants of hepadnaviruses. Seignères, B., Pichoud, C., Martin, P., Furman, P., Trépo, C., Zoulim, F. Hepatology (2002) [Pubmed]
  9. Treating chronic hepatitis B: today and tomorrow. Borgia, G., Gentile, I. Current medicinal chemistry. (2006) [Pubmed]
  10. Mutations of the woodchuck hepatitis virus polymerase gene that confer resistance to lamivudine and 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil. Yamamoto, T., Litwin, S., Zhou, T., Zhu, Y., Condreay, L., Furman, P., Mason, W.S. J. Virol. (2002) [Pubmed]
  11. Comparative evaluation of L-Fd4C and related nucleoside analogs as promising antiviral agents. Chen, S.H. Current medicinal chemistry. (2002) [Pubmed]
  12. Inhibition of hepatitis B virus by a novel L-nucleoside, 2'-fluoro-5-methyl-beta-L-arabinofuranosyl uracil. Balakrishna Pai, S., Liu, S.H., Zhu, Y.L., Chu, C.K., Cheng, Y.C. Antimicrob. Agents Chemother. (1996) [Pubmed]
  13. Phosphorylation of pyrimidine deoxynucleoside analog diphosphates: selective phosphorylation of L-nucleoside analog diphosphates by 3-phosphoglycerate kinase. Krishnan, P., Fu, Q., Lam, W., Liou, J.Y., Dutschman, G., Cheng, Y.C. J. Biol. Chem. (2002) [Pubmed]
  14. Immunization with surface antigen vaccine alone and after treatment with 1-(2-fluoro-5-methyl-beta-L-arabinofuranosyl)-uracil (L-FMAU) breaks humoral and cell-mediated immune tolerance in chronic woodchuck hepatitis virus infection. Menne, S., Roneker, C.A., Korba, B.E., Gerin, J.L., Tennant, B.C., Cote, P.J. J. Virol. (2002) [Pubmed]
  15. Pharmacokinetics of 1-(2-fluoro-5-methyl-beta-L-arabinofuranosyl)uracil in woodchucks. Witcher, J.W., Boudinot, F.D., Baldwin, B.H., Ascenzi, M.A., Tennant, B.C., Du, J.F., Chu, C.K. Antimicrob. Agents Chemother. (1997) [Pubmed]
  16. Inhibitory effect of 2'-fluoro-5-methyl-beta-L-arabinofuranosyl-uracil on duck hepatitis B virus replication. Aguesse-Germon, S., Liu, S.H., Chevallier, M., Pichoud, C., Jamard, C., Borel, C., Chu, C.K., Trépo, C., Cheng, Y.C., Zoulim, F. Antimicrob. Agents Chemother. (1998) [Pubmed]
  17. 19F NMR study of the uptake of 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil in erythrocytes: evidence of transport by facilitated and nonfacilitated pathways. Xu, A.S., Chu, C.K., London, R.E. Biochem. Pharmacol. (1998) [Pubmed]
  18. Reverse transcriptase activity of hepatitis B virus (HBV) DNA polymerase within core capsid: interaction with deoxynucleoside triphosphates and anti-HBV L-deoxynucleoside analog triphosphates. Lam, W., Li, Y., Liou, J.Y., Dutschman, G.E., Cheng, Y.C. Mol. Pharmacol. (2004) [Pubmed]
  19. Structure-activity relationships of 2'-deoxy-2',2'-difluoro-L-erythro-pentofuranosyl nucleosides. Kotra, L.P., Xiang, Y., Newton, M.G., Schinazi, R.F., Cheng, Y.C., Chu, C.K. J. Med. Chem. (1997) [Pubmed]
  20. Behavior of thymidylate kinase toward monophosphate metabolites and its role in the metabolism of 1-(2'-deoxy-2'-fluoro-beta-L-arabinofuranosyl)-5-methyluracil (Clevudine) and 2',3'-didehydro-2',3'-dideoxythymidine in cells. Hu, R., Li, L., Degrève, B., Dutschman, G.E., Lam, W., Cheng, Y.C. Antimicrob. Agents Chemother. (2005) [Pubmed]
  21. Unique metabolism of a novel antiviral L-nucleoside analog, 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil: a substrate for both thymidine kinase and deoxycytidine kinase. Liu, S.H., Grove, K.L., Cheng, Y.C. Antimicrob. Agents Chemother. (1998) [Pubmed]
  22. Use of 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil as a novel antiviral agent for hepatitis B virus and Epstein-Barr virus. Chu, C.K., Ma, T., Shanmuganathan, K., Wang, C., Xiang, Y., Pai, S.B., Yao, G.Q., Sommadossi, J.P., Cheng, Y.C. Antimicrob. Agents Chemother. (1995) [Pubmed]
  23. Management of chronic hepatitis B in treatment-experienced patients. Hui, C.K., Zhang, H.Y., Lau, G.K. Gastroenterol. Clin. North Am. (2004) [Pubmed]
  24. Effect of a combination of clevudine and emtricitabine with adenovirus-mediated delivery of gamma interferon in the woodchuck model of hepatitis B virus infection. Jacquard, A.C., Nassal, M., Pichoud, C., Ren, S., Schultz, U., Guerret, S., Chevallier, M., Werle, B., Peyrol, S., Jamard, C., Rimsky, L.T., Trepo, C., Zoulim, F. Antimicrob. Agents Chemother. (2004) [Pubmed]
  25. Adenovirus-based gene therapy during clevudine treatment of woodchucks chronically infected with woodchuck hepatitis virus. Zhu, Y., Cullen, J.M., Aldrich, C.E., Saputelli, J., Miller, D., Seeger, C., Mason, W.S., Jilbert, A.R. Virology (2004) [Pubmed]
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