Compounds > 9-(2-(phosphonomethoxy)ethyl)adenine diphosphate
Page last updated: 2024-12-08

9-(2-(phosphonomethoxy)ethyl)adenine diphosphate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

9-(2-(phosphonomethoxy)ethyl)adenine diphosphate: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID447863
CHEMBL ID1162433
SCHEMBL ID13394184
MeSH IDM0332363

Synonyms (21)

Synonym
pmea-dp
2-(6-aminopurin-9-yl)ethoxymethyl-[hydroxy(phosphonooxy)phosphoryl]oxy-phosphinic acid
9-(meoet)-a-tp
n-(2-diphosphorylphosphonylmethoxyethyl)-adenine
diphosphoric acid, monoanhydride with [[2-(6-amino-9h-purin-9-yl)ethoxy]methyl]phosphonic acid
pmea-pp
129532-77-0
pmeapp
9-(2-phosphonylmethoxyethyl)adenine diphosphate
(adenin-9-yl-ethoxymethyl)-hydroxyphosphinyl-diphosphate
1PK0
2-(6-aminopurin-9-yl)ethoxymethyl-[hydroxy(phosphonooxy)phosphoryl]oxyphosphinic acid
adefovir diphosphate
CHEMBL1162433
9-(2-(phosphonomethoxy)ethyl)adenine diphosphate
diphosphoric acid, monoanhydride with ((2-(6-amino-9h-purin-9-yl)ethoxy)methyl)phosphonic acid
SCHEMBL13394184
DTXSID60156198
bdbm50479983
Q27459979
((2-(6-amino-9h-purin-9-yl)ethoxy)methyl)phosphonic diphosphoric anhydride

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Dose-limiting nephrotoxicity necessitates suboptimal dosing at 10 mg/day."( Remofovir mesylate: a prodrug of PMEA with improved liver-targeting and safety in rats and monkeys.
Erion, MD; Hong, Z; Lin, CC; Vitarella, D; Yeh, LT, 2004)		0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pathways (2)

PathwayProteinsCompounds
Adefovir Dipivoxil Action Pathway05
Adefovir Dipivoxil Metabolism Pathway46

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Calmodulin-sensitive adenylate cyclaseBacillus anthracisKi0.02700.02700.02700.0270AID977610
Calmodulin-sensitive adenylate cyclaseBacillus anthracisIC50 (µMol)0.03600.03600.03600.0360AID1765314
Reverse transcriptase/RNaseH Human immunodeficiency virus 1IC50 (µMol)30.15000.00011.076810.0000AID395719; AID395720
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Kd7.80000.00062.40599.8000AID395722; AID395723
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Molecular Functions (1)

Processvia Protein(s)Taxonomy
adenylate cyclase activityCalmodulin-sensitive adenylate cyclaseBacillus anthracis
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID395720Inhibition of HIV1 reverse transcriptase p66/p51 K65R mutant expressed in Escherichia coli using calf thymus DNA substrate2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro suppression of K65R reverse transcriptase-mediated tenofovir- and adefovir-5'-diphosphate resistance conferred by the boranophosphonate derivatives.
AID395726Inhibition of HIV1 wild type reverse transcriptase p66/p51 DNA polymerase activity assessed as formation of terminated DNA products2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro suppression of K65R reverse transcriptase-mediated tenofovir- and adefovir-5'-diphosphate resistance conferred by the boranophosphonate derivatives.
AID395729Binding affinity to HIV1 recombinant reverse transcriptase p66/p51 K65R mutant assessed as ratio of catalytic rate constant to Kd for dATP to drug by gel electrophoresis2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro suppression of K65R reverse transcriptase-mediated tenofovir- and adefovir-5'-diphosphate resistance conferred by the boranophosphonate derivatives.
AID395725Binding affinity to HIV1 recombinant reverse transcriptase p66/p51 K65R mutant expressed in Escherichia coli assessed as ratio of catalytic rate constant to Kd for incorporation of drug to DNA by gel electrophoresis2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro suppression of K65R reverse transcriptase-mediated tenofovir- and adefovir-5'-diphosphate resistance conferred by the boranophosphonate derivatives.
AID395719Inhibition of HIV1 wild type reverse transcriptase p66/p51 expressed in Escherichia coli using calf thymus DNA substrate2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro suppression of K65R reverse transcriptase-mediated tenofovir- and adefovir-5'-diphosphate resistance conferred by the boranophosphonate derivatives.
AID395728Binding affinity to HIV1 wild type reverse transcriptase p66/p51 assessed as ratio of catalytic rate constant to Kd for dATP to drug by gel electrophoresis2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro suppression of K65R reverse transcriptase-mediated tenofovir- and adefovir-5'-diphosphate resistance conferred by the boranophosphonate derivatives.
AID395722Binding affinity to HIV1 wild type reverse transcriptase p66/p51 expressed in Escherichia coli assessed as incorporation of drug to DNA by gel electrophoresis2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro suppression of K65R reverse transcriptase-mediated tenofovir- and adefovir-5'-diphosphate resistance conferred by the boranophosphonate derivatives.
AID395721Ratio of IC50 for HIV1 reverse transcriptase p66/p51 K65R mutant to IC50 for HIV1 wild type reverse transcriptase2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro suppression of K65R reverse transcriptase-mediated tenofovir- and adefovir-5'-diphosphate resistance conferred by the boranophosphonate derivatives.
AID395723Binding affinity to HIV1 recombinant reverse transcriptase p66/p51 K65R mutant expressed in Escherichia coli assessed as incorporation of drug to DNA by gel electrophoresis2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro suppression of K65R reverse transcriptase-mediated tenofovir- and adefovir-5'-diphosphate resistance conferred by the boranophosphonate derivatives.
AID1765314Inhibition of Bacillus anthracis edema factor by cell free assay2021European journal of medicinal chemistry, Oct-15, Volume: 222Acyclic nucleoside phosphonates with 2-aminothiazole base as inhibitors of bacterial and mammalian adenylate cyclases.
AID395724Binding affinity to wild type reverse transcriptase assessed as ratio of catalytic rate constant to Kd for incorporation of drug to DNA by gel electrophoresis2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro suppression of K65R reverse transcriptase-mediated tenofovir- and adefovir-5'-diphosphate resistance conferred by the boranophosphonate derivatives.
AID395727Inhibition of HIV1 wild type reverse transcriptase p66/p51 R72A mutant DNA polymerase activity assessed as formation of terminated DNA products2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
In vitro suppression of K65R reverse transcriptase-mediated tenofovir- and adefovir-5'-diphosphate resistance conferred by the boranophosphonate derivatives.
AID1765315Inhibition of Bordetella pertussis ACT by cell free assay2021European journal of medicinal chemistry, Oct-15, Volume: 222Acyclic nucleoside phosphonates with 2-aminothiazole base as inhibitors of bacterial and mammalian adenylate cyclases.
AID1811Experimentally measured binding affinity data derived from PDB2004Proceedings of the National Academy of Sciences of the United States of America, Mar-02, Volume: 101, Issue:9
Selective inhibition of anthrax edema factor by adefovir, a drug for chronic hepatitis B virus infection.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2004Proceedings of the National Academy of Sciences of the United States of America, Mar-02, Volume: 101, Issue:9
Selective inhibition of anthrax edema factor by adefovir, a drug for chronic hepatitis B virus infection.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (11.11)18.2507
2000's5 (55.56)29.6817
2010's2 (22.22)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.64

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.64 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index5.04 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.64)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		3.29606-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
1h-3-benzazepin-7-ol, 8-bromo-2,3,4,5-tetrahydro-3-methyl-5-phenyl-
1H-3-benzazepin-7-ol, 8-bromo-2,3,4,5-tetrahydro-3-methyl-5-phenyl-: stereoselective antagonist of dopamine receptor		2.3110benzazepine
sq 22536
9-(tetrahydrofuryl)adenine : A nucleoside analogue that is adenine in which the nitrogen at position 9 has been substituted by a tetrahydrofuran-2-yl group. It is an adenylate cyclase inhibitor.		2.3110nucleoside analogue;
oxolanes		EC 4.6.1.1 (adenylate cyclase) inhibitor
2'-deoxyadenosine triphosphate
2'-deoxyadenosine triphosphate: RN given refers to unlabeled parent cpd		2.03102'-deoxyadenosine 5'-phosphate;
purine 2'-deoxyribonucleoside 5'-triphosphate		Escherichia coli metabolite;
mouse metabolite
adefovir
adefovir: inhibitor of African swine fever virus. adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).. adefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.		2106-aminopurines;
ether;
phosphonic acids		antiviral drug;
DNA synthesis inhibitor;
drug metabolite;
HIV-1 reverse transcriptase inhibitor;
nephrotoxic agent
adefovir dipivoxil
bis(pivaloyloxymethyl)-9-(2-phosphonylmethoxyethyl)adenine: structure given in first source. adefovir pivoxil : An organic phosphonate that is the dipivoxil ester of adefovir. A prodrug for adefovir, an HIV-1 reverse transcriptase inhibitor, adefovir pivoxil is used to treat chronic hepatitis B viral infection.		2.45206-aminopurines;
carbonate ester;
ether;
organic phosphonate		antiviral drug;
DNA synthesis inhibitor;
HIV-1 reverse transcriptase inhibitor;
nephrotoxic agent;
prodrug
organophosphonates
hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.		2.9440divalent inorganic anion;
phosphite ion
phosphorus
Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.		2.1110monoatomic phosphorus;
nonmetal atom;
pnictogen		macronutrient
pradefovir mesylate
pradefovir: a HepDirect prodrug of adefovir; structure in first source		2.0210
ConditionIndicatedRelationship StrengthStudiesTrials
Chronic Hepatitis B
[description not available]		02.4220
Hepatitis B, Chronic
INFLAMMATION of the LIVER in humans caused by HEPATITIS B VIRUS lasting six months or more. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.		02.4220
Nerve Pain
[description not available]		02.3110
Neuralgia
Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.		02.3110
HIV Coinfection
[description not available]		02.0410
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		02.0410