An active metabolite of adefovir dipivoxil
Related Products
Labeled Version(s)
31315Adefovir-d4
Pro-drug Form(s)
28373Adefovir dipivoxil 45047Pradefovir (mesylate)
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Adefovir

Item No. 18650

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
P-[[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]-phosphonic acid
CAS Number
106941-25-7
Synonyms
  • GS-0393
  • PMEA
Molecular Formula
C8H12N5O4P
Formula Weight
273.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
SMILES
NC1=C2C(N(CCOCP(O)(O)=O)C=N2)=NC=N1
InChi Code
InChI=1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)
InChi Key
SUPKOOSCJHTBAH-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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    10 mg

    $36

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    50 mg

    $153

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    100 mg

    $268

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    250 mg

    $587

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    Cayman Chemical
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    Product Description

    Adefovir is an active metabolite of the antiviral nucleoside analog adefovir dipivoxil (Item No. 28373).1 Adefovir is formed from adefovir dipivoxil by gastrointestinal carboxylesterase 2 (CES2).2 It inhibits cytopathogenicity induced by herpes simplex virus 1 (HSV-1) and HSV-2 (EC50 = 7 µg/ml for both in E6SM cells), HIV-1 and HIV-2 (EC50s = 1.8 and 2.5 µg/ml, respectively, in CEM cells), and varicella zoster virus (VZV; EC50 = 10 µg/ml in human embryonic lung fibroblasts).3 Adefovir (50 mg/kg, p.o.) reduces increases in lymph node viral DNA and serum IgG levels in a mouse model of AIDS induced by infection with the retroviral complex LP-BM5.4 It also inhibits tumor growth induced by Moloney sarcoma virus (MSV) infection in mice at the same dose.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Arimilli, M.N., Dougherty, J.P., Cundy, K.C., et al. Orally bioavailable acyclic nucleoside phosphonate prodrugs: Adefovir dipivoxil and bis(POC)PMPA. Advances in Antiviral Drug Design 3, 69-91 (1999).

    2. Laizure, S.C., Herring, V., Hu, Z., et al. The role of human carboxylesterases in drug metabolism: Have we overlooked their importance? Pharmacotherapy 33(2), 210-222 (2013).

    3. Holý, A., Votruba, I., Masojídková, M., et al. 6-[2-(Phosphonomethoxy)alkoxy]pyrimidines with antiviral activity. J. Med. Chem. 45(9), 1918-1929 (2002).

    4. Rossi, L., Dominici, S., Serafini, S., et al. Pharmacokinetic and antiretroviral activity in mice of oral [P1,P2-bis[2-(adenin-9-yl)ethoxymethyl]phosphonate], a prodrug of 9-(2-phosphonylmethoxyethyl)adenine. J. Antimicrob. Chemother. 50(3), 365-374 (2002).

    5. Naesens, L., Balzarini, J., Bischofberger, N., et al. Antiretroviral activity and pharmacokinetics in mice of oral bis(pivaloyloxymethyl)-9-(2-phosphonylmethoxyethyl)adenine, the bis(pivaloyloxymethyl) ester prodrug of 9-(2-phosphonylmethoxyethyl)adenine. Antimicrob. Agents Chemother. 40(1), 22-28 (1996).