An antiviral nucleoside analog
Related Products
Alternative(s)
36926Entecavir
Labeled Version(s)
37212Entecavir-d2
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Entecavir (hydrate)

Item No. 13831

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one, monohydrate
CAS Number
209216-23-9
Synonyms
  • BMS 200475
  • SQ 34,676
Molecular Formula
C12H15N5O3 • H2O
Formula Weight
295.3
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 12 mg/mlEthanol: 0.1 mg/ml
λmax
256 nm
SMILES
NC(NC1=C2N=CN1[C@H]3C[C@H](O)[C@@H](CO)C3=C)=NC2=O.O
InChi Code
InChI=1S/C12H15N5O3.H2O/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20;/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20);1H2/t6-,7-,8-;/m0./s1
InChi Key
YXPVEXCTPGULBZ-WQYNNSOESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Cayman Chemical
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    Product Description

    Entecavir is an antiviral nucleoside analog of 2'-deoxyguanosine (Item No. 9002864) and inhibitor of hepatitis B virus (HBV) reverse transcriptase (IC50 = 0.5 nM).1,2 It undergoes phosphorylation by cellular kinases to its active form, entecavir triphosphate.3,2 Entecavir reduces virion DNA in the culture supernatant of HepG2 2.2.15 cells infected with hepatitis B virus (HBV; EC50 = 3.75 nM).1 It reduces serum and hepatic levels of viral DNA in a duckling model of HBV infection when administered at a dose of 1 mg/kg.4 Formulations containing entecavir have been used in the treatment of chronic HBV infection.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Innaimo, S.F., Seifer, M., Bisacchi, G.S., et al. Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus. Antimicrob. Agents Chemother. 41(7), 1444-1448 (1997).

    2. Langley, D.R., Walsh, A.W., Baldick, C.J., et al. Inhibition of hepatitis B virus polymerase by entecavir. J. Virol. 81(8), 3992-4001 (2007).

    3. 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).

    4. Marion, P.L., Salazar, F.H., Winters, M.A., et al. Potent efficacy of entecavir (BMS-200475) in a duck model of hepatitis B virus replication. Antimicrob. Agents Chemother. 46(1), 82-88 (2002).