SKU: C213  / 
    CAS Number: 20724-73-6

    2'-C-Methylcytidine

    $315.36 - $678.24

    2’-C-Methylcytidine (syn: 2CMC) is a viral replication inhibitor, shown to be active against multiple viruses including hepatitis C virus (HCV), inhibiting the HCV NS5B RNA polymerase.  It is also used against other viruses including Norwalk, West Nile, dengue, foot-and-mouth, and yellow fever.  The compound is a ribonucleoside analog and acts as a bioactive small molecule inhibitor of viral nucleoside polymerase.

    2’-C-Methylcytidine is sparingly soluble in water.

    Application 2’-C-Methylcytidine is useful for the development of antiviral research compounds.
    Mechanism of Action 2’-C-Methylcytidine has been shown to be a small-molecule inhibitor of viral nucleoside polymerase.  In hepatitis C virus, it inhibits HCV NS5B RNA polymerase.

    In studies with foot-and-mouth disease, experiments suggest that the compound interacts with the viral replication that coincides with the onset of intracellular viral RNA synthesis.

    Spectrum 2’-C-Methylcytidine can be used for multiple viruses including hepatitis C virus (HCV), Norwalk virus, and bovine pestivirus.  It is also effective for three flaviviruses including yellow fever virus, West Nile virus, and dengue-2 virus.  It has in vitro activity against coxsackievirus causing hand-foot-and-mouth disease and yellow fever virus.
    Microbiology Applications NM 283 is an efficient prodrug of 2’-C-methylcytidine.  It is an 3’-O-L-valinyl ester derivative.  It is a promising antiviral for HCV infection (Pierra et al, 2011).

    Studies in a cell-based replicon assay indicated that several of the phosphoaramidates including NM 283 demonstrated a 10- to 200-fold potency due to higher levels of 2’-C-methylcytidine triphosphate in the cells. These prodrugs are converted to the triphosphate in hepatocytes (Gardelli et al, 2009).

    Molecular Formula C10H15N3O5
    References

    Gardelli et al (2009)  Phosphoramidate prodrugs of 2’-C-Methylcytidine for therapy of Hepatitis C virus infection. J. Med. Chem. 52(17):5394-5407  PMID 19725579

    Julander JG et al (2010)  Efficacy of 2’-C-Methylcytidine against yellow fever virus in cell culture and in a hamster model. Antivir. Res. 86(3):261-267  PMID 20227442

    Nesya G et al (2007)  2’-C-Methylcytidine as a potent and selective inhibitor of the replication of foot-and-mouth disease virus. Antiviral Res. 73(3):161-168  PMID 17055073

    Lee J et al (2015)  Characterization of the activity of 2’-C-Methylcytidine against dengue virus replication. Antiviral Res. 116:1-9  PMID 25614455

    Pierra et al (2006)  Synthesis and pharmacokinetics of Valopicitabine (NM283), an efficient prodrug of the potent anti-HCV agent 2'-C-Methylcytidine. J. Med. Chem. 49(22):6614-6620  PMID 17064080

    Pierra C et al (2011)  NM 283, An efficient prodrug of the potent anti-HCV agent 2’-C-Methylcytidine. Nucleosides, Nucleotides and Nucl. Acids 24(5-7):767-770

    Rocha-Pereira JD et al (2013)  The viral polymerase inhibitor 2'-C-Methylcytidine inhibits Norwalk virus replication and protects against Norovirus-induced diarrhea and mortality in a mouse model. J. Virol.  87(21):11798-1805  PMID 23986582