An antiviral nucleoside analog
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Clevudine

Item No. 30612

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione
CAS Number
163252-36-6
Synonyms
  • Levovir
  • L-FMAU
Molecular Formula
C10H13FN2O5
Formula Weight
260.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 30 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
210, 265 nm
SMILES
O=C(C(C)=CN1[C@]2([H])[C@H](F)[C@@H](O)[C@H](CO)O2)NC1=O
InChi Code
InChI=1S/C10H13FN2O5/c1-4-2-13(10(17)12-8(4)16)9-6(11)7(15)5(3-14)18-9/h2,5-7,9,14-15H,3H2,1H3,(H,12,16,17)/t5-,6+,7-,9-/m0/s1
InChi Key
GBBJCSTXCAQSSJ-XQXXSGGOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Clevudine is a β-L-nucleoside analog of thymidine (Item No. 20519) that has antiviral activity.1,2,3 It is active against hepatitis B virus (HBV) in HepG2/2.15 cells with an EC50 value of 0.1 µM.3 Clevudine (0.01-10 µM) reduces virion DNA in the culture supernatant of primary hepatocytes isolated from a duckling model of chronic HBV infection.4 Oral administration of clevudine (3 and 10 mg/kg) reduces serum viral load in a woodchuck model of chronic HBV infection.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Painter, G.R., Trost, L.C., Blum, M.R., et al. Clevudine: A novel 1-β-L nucleoside analogue in clinical development for the treatment of HBV infection. Frontiers in Viral Hepatitis 281-300 (2003).

    2. Fung, J., Lai, C.-L., Seto, W.-K., et al. Nucleoside/nucleotide analogues in the treatment of chronic hepatitis B. J. Antimicrob. Chemother. 66(12), 2715-2725 (2011).

    3. Chu, C.K., Ma, T., Shanmuganathan, K., et al. Use of 2'-fluoro-5-methyl-β-L-arabinofuranosyluracil as a novel antiviral agent for hepatitis B virus and Epstein-Barr virus. Antimicrob. Agents Chemother. 39(4), 979-981 (1995).

    4. Aguesse-Germon, S., Liu, S.-H., Chevallier, M., et al. Inhibitory effect of 2'-fluoro-5-methyl-β-L-arabinofuranosyl-uracil on duck hepatitis B virus replication. Antimicrob. Agents Chemother. 42(2), 369-376 (1998).

    5. Peek, S.F., Cote, P.J., Jacob, J.R., et al. Antiviral activity of clevudine [L-FMAU, (1-(2-fluoro-5-methyl-β, L-arabinofuranosyl) uracil)] against woodchuck hepatitis virus replication and gene expression in chronically infected woodchucks (Marmota monax). Hepatology 33(1), 254-266 (2001).