A potent, broad-spectrum antiviral agent
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Pro-drug Form(s)
16757Ribavirin
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Ribavirin 5'-monophosphate (lithium salt)

Item No. 21821

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(5-O-phosphono-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide, dilithium salt
CAS Number
66983-94-6
Molecular Formula
C8H11N4O8P • 2Li
Formula Weight
336.1
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
O[C@@H]1[C@@H](COP([O-])([O-])=O)O[C@@H](N2N=C(C(N)=O)N=C2)[C@@H]1O.[Li+].[Li+]
InChi Code
InChI=1S/C8H13N4O8P.2Li/c9-6(15)7-10-2-12(11-7)8-5(14)4(13)3(20-8)1-19-21(16,17)18;;/h2-5,8,13-14H,1H2,(H2,9,15)(H2,16,17,18);;/q;2*+1/p-2/t3-,4-,5-,8-;;/m1../s1
InChi Key
SIMMZIYZANJRNU-DAVOPPATSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Ribavirin 5'-monophosphate inhibits viral DNA and RNA replication in vitro via the strong competitive inhibition of inosine monophosphate dehydrogenase (IMPDH), with a reported Ki value of 270 nM, and thus inhibits guanosine triphosphate synthesis.1,2,3 This agent, a metabolite of the prodrug ribavirin (Item No. 16757), exhibits broad-spectrum antiviral activity, particularly against myxoviruses.2,3 The antiviral effects of ribavirin require conversion to the monophosphate form via adenosine kinase.1,3 The anti-HIV activity of ribavirin in cultured human lymphocytes, as well as the anti-influenza activity of this prodrug in MDCK cells, have been attributed to ribavirin 5'-monophosphate.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Willis, R.C., Carson, D.A., and Seegmiller, J.E. Adenosine kinase initiates the major route of ribavirin activation in a cultured human cell line. Proc. Natl. Acad. Sci. USA 75(7), 3042-3044 (1978).

    2. Streeter, D.J., Witkowski, J.T., Khare, G.P., et al. Mechanism of action of 1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide (virazole), a new broad-spectrum antiviral agent. Proc. Natl. Acad. Sci. USA 70(4), 1174-1178 (1973).

    3. De Clercq, E. Specific targets for antiviral drugs. Biochem. J. 205, 1-13 (1982).

    4. Balzarini, J., Lee, C.-K., Herdewijn, P., et al. Mechanism of the potentiating effect of ribavirin on the activity of 2’,3’-dideoxyinosine against human immunodeficiency virus. The Journal of Biological Chemisty 266(32), 21509-21514 (1991).

    5. Browne, M.J. Mechanism and specificity of action of ribavirin. Antimicrob. Agents Chemother. 15(6), 747-753 (1979).