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Chemical Compound Review

TCNR     1-[(3R,4S,5R)-3,4-dihydroxy- 5...

Synonyms: AG-K-84088, SureCN4958886, KST-1B4952, KST-1B4953, AC1L4QIR, ...
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Disease relevance of 1-[(3R,4R,5R)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-1,2,4-triazole-3-carboxamidine

  • For example, potent and HDV-specific inhibition, in the absence of detected host toxicity, could be obtained with ribavirin, mycophenolic acid, and viramidine [1].
  • An investigational nucleoside analogue drug, viramidine, has recently emerged as a potentially safer alternative to ribavirin for the treatment of hepatitis C viral infection [2].
  • Ribamidine (1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine) was inhibitory in rhesus monkey kidney (LLC-MK2 derivative) cells to Adames and Balliet strains of Punta Toro virus (PTV), a Phlebovirus related to Rift Valley fever and sandfly fever viruses [3].
  • In the 1-month study in rats, viramidine or ribavirin dosing at 120 mg/kg/day reduced Hgb concentrations (12-16% and 13-20% compared to controls, respectively) and caused slight erythroid hyperplasia in the bone marrow [4].
  • In September 2000, phase I trials began in Europe. In December 2001, the company filed a US IND for the clinical development of viramidine as part of a combination therapy with interferon-afor the treatment of chronic hepatitis C virus (HCV) infection [435007], [441613]; a phase I trial was initiated in the US in late March 2002 [435598] [5].

High impact information on 1-[(3R,4R,5R)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-1,2,4-triazole-3-carboxamidine


Chemical compound and disease context of 1-[(3R,4R,5R)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-1,2,4-triazole-3-carboxamidine


Biological context of 1-[(3R,4R,5R)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-1,2,4-triazole-3-carboxamidine


Anatomical context of 1-[(3R,4R,5R)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-1,2,4-triazole-3-carboxamidine


Associations of 1-[(3R,4R,5R)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-1,2,4-triazole-3-carboxamidine with other chemical compounds


Gene context of 1-[(3R,4R,5R)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-1,2,4-triazole-3-carboxamidine


Analytical, diagnostic and therapeutic context of 1-[(3R,4R,5R)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-1,2,4-triazole-3-carboxamidine


  1. Action of inhibitors on accumulation of processed hepatitis delta virus RNAs. Chang, J., Nie, X., Gudima, S., Taylor, J. J. Virol. (2006) [Pubmed]
  2. Dual-action mechanism of viramidine functioning as a prodrug and as a catabolic inhibitor for ribavirin. Wu, J.Z., Larson, G., Hong, Z. Antimicrob. Agents Chemother. (2004) [Pubmed]
  3. Effects of ribamidine, a 3-carboxamidine derivative of ribavirin, on experimentally induced Phlebovirus infections. Sidwell, R.W., Huffman, J.H., Barnard, D.L., Pifat, D.Y. Antiviral Res. (1988) [Pubmed]
  4. Viramidine demonstrates better safety than ribavirin in monkeys but not rats. Dadgostari, S., Xu, C., Yeh, L.T., Lin, C.C., Vitarella, D. Drug and chemical toxicology. (2004) [Pubmed]
  5. Viramidine (Ribapharm). Barnard, D. Current opinion in investigational drugs (London, England : 2000) (2002) [Pubmed]
  6. Absorption, metabolism, and excretion of [14C]viramidine in humans. Lin, C.C., Xu, C., Zhu, N., Yeh, L.T. Antimicrob. Agents Chemother. (2006) [Pubmed]
  7. Phosphorylation of ribavirin and viramidine by adenosine kinase and cytosolic 5'-nucleotidase II: Implications for ribavirin metabolism in erythrocytes. Wu, J.Z., Larson, G., Walker, H., Shim, J.H., Hong, Z. Antimicrob. Agents Chemother. (2005) [Pubmed]
  8. Prospects for hepatitis C virus therapeutics: levovirin and viramidine as improved derivatives of ribavirin. Watson, J. Current opinion in investigational drugs (London, England : 2000) (2002) [Pubmed]
  9. Pharmacokinetics and safety of viramidine, a prodrug of ribavirin, in healthy volunteers. Lin, C.C., Philips, L., Xu, C., Yeh, L.T. Journal of clinical pharmacology. (2004) [Pubmed]
  10. Effect of ribavirin, levovirin and viramidine on liver toxicological gene expression in rats. Fang, C., Srivastava, P., Lin, C.C. Journal of applied toxicology : JAT. (2003) [Pubmed]
  11. In vitro and in vivo influenza virus-inhibitory effects of viramidine. Sidwell, R.W., Bailey, K.W., Wong, M.H., Barnard, D.L., Smee, D.F. Antiviral Res. (2005) [Pubmed]
  12. Conversion of viramidine to ribavirin in vivo by adenosine deaminase and its inhibition by 2'-deoxycoformycin. Wu, J.Z., Yeh, L.T., Lin, C.C., Hong, Z. Antivir. Chem. Chemother. (2006) [Pubmed]
  13. Ascending multiple-dose pharmacokinetics of viramidine, a prodrug of ribavirin, in adult subjects with compensated hepatitis C infection. Aora, S., Xu, C., Teng, A., Peterson, J., Yeh, L.T., Gish, R., Lau, D., Rossi, S., Lin, C.C. Journal of clinical pharmacology. (2005) [Pubmed]
  14. LC-MS/MS method for simultaneous determination of viramidine and ribavirin levels in monkey red blood cells. Yeh, L.T., Nguyen, M., Dadgostari, S., Bu, W., Lin, C.C. Journal of pharmaceutical and biomedical analysis (2007) [Pubmed]
  15. Pharmacokinetics and metabolism of [14C]viramidine in rats and cynomolgus monkeys. Lin, C.C., Luu, K., Lourenco, D., Yeh, L.T. Antimicrob. Agents Chemother. (2003) [Pubmed]
  16. Activation and deactivation of a broad-spectrum antiviral drug by a single enzyme: adenosine deaminase catalyzes two consecutive deamination reactions. Wu, J.Z., Walker, H., Lau, J.Y., Hong, Z. Antimicrob. Agents Chemother. (2003) [Pubmed]
  17. Viramidine, a prodrug of ribavirin, shows better liver-targeting properties and safety profiles than ribavirin in animals. Lin, C.C., Yeh, L.T., Vitarella, D., Hong, Z. Antivir. Chem. Chemother. (2003) [Pubmed]
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