An antiviral prodrug
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Active Metabolite(s)
18650Adefovir
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Adefovir dipivoxil

Item No. 28373

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,2-dimethyl-propanoic acid, 1,1′-[[[[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]phosphinylidene]bis(oxymethylene)] ester
CAS Number
142340-99-6
Synonyms
  • GS 0840
Molecular Formula
C20H32N5O8P
Formula Weight
501.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
260 nm
SMILES
O=C(OCOP(OCOC(C(C)(C)C)=O)(COCCN1C2=NC=NC(N)=C2N=C1)=O)C(C)(C)C
InChi Code
InChI=1S/C20H32N5O8P/c1-19(2,3)17(26)30-11-32-34(28,33-12-31-18(27)20(4,5)6)13-29-8-7-25-10-24-14-15(21)22-9-23-16(14)25/h9-10H,7-8,11-13H2,1-6H3,(H2,21,22,23)
InChi Key
WOZSCQDILHKSGG-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 mg

    $41

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    50 mg

    $75

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    100 mg

    $142

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    Cayman Chemical
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    Product Description

    Adefovir dipivoxil is a prodrug form of the antiviral nucleoside analog adefovir (Item No. 18650).1 Adefovir dipivoxil inhibits hepatitis B virus (HBV) DNA synthesis in HepG2 2.2.15 cells infected with HBV (EC50 = 0.517 μM).2 It is cytotoxic to HepG2 2.2.15 cells with a 50% cytotoxicity concentration (CC50) value of 540 μM. Adefovir dipivoxil inhibits HBV replication in the liver of HBV transgenic mice (ED50 = 0.2 μmol/kg per day).3 Formulations containing adefovir dipivoxil 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. Liu, L.J., Wang, J.H., Du, S.C., et al. rtE218G, a novel hepatitis B virus mutation with resistance to adefovir dipivoxil in patients with chronic hepatitis B. J. Viral Hepat. 17(Suppl. 1), 66-72 (2010).

    2. Fu, X., Jiang, S., Li, C., et al. Design and synthesis of novel bis(L-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) with improved anti-HBV activity. Bioorg. Med. Chem. Lett. 17(2), 465-470 (2007).

    3. Morrey, J.D., Korba, B.E., Beadle, J.R., et al. Alkoxyalkyl esters of 9-(s)-(3-hydroxy-2-phosphonomethoxypropyl) adenine are potent and selective inhibitors of hepatitis B virus (HBV) replication in vitro and in HBV transgenic mice in vivo. Antimicrob. Agents Chemother. 53(7), 2865-2870 (2009).