Adefovir Dipivoxil is a acyclic nucleotide analog reverse transcriptase inhibitor (ntRTI). It is phosphorylated to the active metabolite adefovir diphosphate by cellular kinases. Adefovir diphosphate inhibits HBV DNA polymerase (reverse transcriptase) by competing with the natural substrate deoxyadenosine triphosphate and by causing DNA chain termination after its incorporation into viral DNA.
CAT No: 10-101-107
CAS No:142340-99-6
Synonyms/Alias:Adefovir di(pivaloyloxymethyl) ester;Bis(POM)PMEA; GS-0840; Piv2PMEA;9-[2-(Bis[(pivaloyloxy)-methoxy]phosphinylmethoxy)ethyl]adenine
Chemical Name:[2-(6-aminopurin-9-yl)ethoxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate
Adefovir Dipivoxil is a nucleotide analogue prodrug that has become a valuable tool in biochemical and molecular biology research due to its unique capacity to inhibit viral DNA polymerases. As a phosphonate ester derivative, it undergoes intracellular conversion to its active metabolite, adefovir, which structurally mimics natural nucleotides and interferes with the replication processes of various DNA viruses. Its mechanism of action, based on the competitive inhibition of viral polymerases and subsequent chain termination, renders it particularly significant for in vitro studies focused on viral replication, nucleotide metabolism, and antiviral drug resistance. The compound's biochemical versatility and well-characterized mode of action make it a preferred choice for researchers investigating nucleotide analogues and their interactions within cellular systems.
Antiviral Mechanism Studies: In virology research, adefovir dipivoxil serves as a model compound for elucidating the molecular mechanisms underlying nucleotide analogue-mediated inhibition of viral DNA synthesis. By incorporating into nascent viral DNA strands and causing premature termination, it allows investigators to dissect the kinetics and structural requirements of viral polymerases. These studies are instrumental in advancing the understanding of how nucleotide analogues disrupt viral replication, which is essential for the rational design of next-generation antiviral agents.
Resistance Profiling: The compound is extensively utilized in laboratory settings to investigate the emergence and characterization of viral resistance mutations. By applying selective pressure in cell culture systems, researchers can observe the development of resistance-associated variants and map mutations within viral polymerase genes. Insights gained from these experiments inform both the development of new antiviral compounds and the optimization of combination therapy strategies, contributing to the broader field of antiviral resistance management.
Pharmacokinetic and Metabolic Studies: As a prodrug, adefovir dipivoxil is frequently employed in studies examining prodrug activation, cellular uptake, and metabolic conversion pathways. Researchers use it to assess the efficiency of ester hydrolysis, intracellular phosphorylation, and the formation of pharmacologically active metabolites. These investigations enhance the understanding of prodrug design principles, facilitating the development of more effective and bioavailable nucleotide analogues for research applications.
Drug Interaction Research: The compound's interaction with various cellular enzymes and transporters makes it a valuable model for studying potential drug-drug interactions at the molecular level. Scientists utilize it to evaluate the influence of co-administered agents on prodrug activation, transporter-mediated uptake, and intracellular nucleotide pools. Such studies are critical for predicting and mitigating adverse interactions in preclinical research, as well as for optimizing the pharmacological profiles of new nucleotide-based compounds.
Analytical Method Development: Owing to its defined chemical structure and metabolic profile, adefovir dipivoxil is often used as a reference standard in the development and validation of analytical methods. Techniques such as high-performance liquid chromatography and mass spectrometry rely on its inclusion for the accurate quantification of nucleotide analogues and their metabolites in biological matrices. These analytical applications support rigorous quality control and pharmacological research, ensuring the reliability and reproducibility of experimental results involving nucleotide-based agents.
Tenofovir disoproxil fumarate (DF) is a nucleotide analogue and a potent inhibitor of human immunodeficiency virus type 1 reverse transcriptase and hepatitis B virus (HBV) polymerase.
Marcellin P, Heathcote E J, Buti M, et al. Tenofovir disoproxil fumarate versus adefovir dipivoxil for chronic hepatitis B[J]. New England Journal of Medicine, 2008, 359(23): 2442-2455.
Adefovir dipivoxil possesses potent in vitro and in vivo antiviral activity in wild-type hepatitis B. This study assessed the safety and efficacy of adefovir dipivoxil alone and in combination with lamivudine compared with ongoing lamivudine therapy in patients with chronic hepatitis B with compensated liver disease and lamivudine-resistant hepatitis B virus (HBV).
Peters M G, Hann H W, Martin P, et al. Adefovir dipivoxil alone or in combination with lamivudine in patients with lamivudine-resistant chronic hepatitis B[J]. Gastroenterology, 2004, 126(1): 91-101.
Adefovir dipivoxil effectively inhibits both hepatitis B virus (HBV) replication and disease activity in patients with chronic hepatitis B. Resistance to treatment was not observed in 2 recent large placebo-controlled 48-week studies with this drug. The aim of this study was to characterize adefovir resistance in a patient who developed clinical and virologic evidence of breakthrough during a 96-week course of treatment.
Angus P, Vaughan R, Xiong S, et al. Resistance to adefovir dipivoxil therapy associated with the selection of a novel mutation in the HBV polymerase[J]. Gastroenterology, 2003, 125(2): 292-297.
Oral adefovir dipivoxil is effective and generally well tolerated in HBeAg-positive and -negative patients chronically infected with wild-type or lamivudine-resistant HBV. Few resistant HBV mutants have emerged to date. Data from ongoing long-term studies are awaited with interest. Existing treatment options for patients with chronic hepatitis B are limited in both number and effectiveness; the proven efficacy, good tolerability profile and apparently low potential for resistance of adefovir dipivoxil make it a promising new option in the management of this disease.
Dando T M, Plosker G L. Adefovir dipivoxil: a review of its use in chronic hepatitis B[J]. Drugs, 2003, 63(20): 2215-2235.
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