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3'-azido-3'-deoxythymidine 5'phosphate

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Description

3'-azido-3'-deoxythymidine 5'phosphate, commonly known as AZT, is a nucleoside analog that inhibits the activity of HIV-1 reverse transcriptase. It was the first antiretroviral drug approved for the treatment of HIV infection. AZT is a synthetic analog of thymidine, one of the four nucleosides found in DNA. AZT is a chain terminator, meaning that it stops the replication of the HIV virus by preventing the incorporation of nucleotides into the viral DNA chain. AZT is typically administered orally. It has a wide range of side effects, including anemia, neutropenia, and lactic acidosis. AZT was synthesized in 1964 by Jerome Horwitz at the Michigan Cancer Foundation. It was originally developed as an anticancer drug, but it was later found to be effective against HIV. AZT is still widely used in the treatment of HIV infection, but it has been largely replaced by more effective and less toxic antiretroviral drugs.'

3'-azido-3'-deoxythymidine 5'phosphate: inhibits thymidylate kinase [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65374
CHEMBL ID257695
SCHEMBL ID15094301
MeSH IDM0160359

Synonyms (31)

Synonym
3'-azido-2',3'-dideoxythymidine-5'-monophosphate
azddtmp
zidovudine monophosphate
[(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
azt-mp
5'-thymidylic acid, 3'-azido-3'-deoxy-
azt-monophosphate
nsc742230
aztmp
zdv 5'-monophosphate
zdvmp
3'-azido-2',3'-deoxythymidine 5'-monophosphate
DB03666
3'-azido-3'-deoxythymidine 5'-phosphate
zidovudine 5'-monophosphate
CHEMBL257695
3'-azido-3'-deoxythymidine monophosphate
[(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate
unii-97ymu05vpj
3'-azido-3'-deoxythymidine 5'phosphate
97ymu05vpj ,
29706-85-2
3'-azido-3'-deoxythymidine 5'-monophosphate sodium salt
azt 5'-monophosphate
azidothymidine monophosphate
SCHEMBL15094301
DTXSID30183855
bdbm50478975
3'-azido-3'-deoxythymidine 5'-(dihydrogen phosphate)
OIFWQOKDSPDILA-XLPZGREQSA-N
Q27272049

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Intersubject pharmacokinetic variability for zidovudine is substantial, but intravenous therapy provides plasma concentrations and intracellular zidovudine triphosphate levels consistent with high antiviral activity."( Systemic pharmacokinetics and cellular pharmacology of zidovudine in human immunodeficiency virus type 1-infected women and newborn infants.
Bardeguez, AD; Blanchard, S; Flynn, PM; Fridland, A; Jimenez, E; Robbins, B; Rodman, JH; Rodriguez, JF, 1999
)
0.3

Dosage Studied

ExcerptRelevanceReference
"In vitro studies of zidovudine (ZDV) phosphorylation may not accurately reflect the in vivo dose-response relationship, which is crucial to determining the relationship between ZDV exposure, efficacy, and toxicity."( Intracellular zidovudine (ZDV) and ZDV phosphates as measured by a validated combined high-pressure liquid chromatography-radioimmunoassay procedure.
Hamzeh, FM; Kornhauser, DM; Kuwahara, SK; Lewis, LD; Lietman, PS; Slusher, JT, 1992
)
0.28
"4 pmoles/10(6) cells) followed a nonlinear dose-response relationship over the range 0-50 microM extracellular ZDV, with concentration-dependent saturation."( In vitro measurement of phosphorylated zidovudine in peripheral blood leucocytes.
Hurtubise, PE; Pesce, AJ; Stretcher, BN; Wermeling, JR, 1990
)
0.28
"The plasma and intracellular phosphorylated metabolite concentrations of ZDV were determined over a 12 h period following oral administration of 100 and 300 mg ZDV to 10 HIV-seropositive patients at steady state during two dosing regimens (i."( The effect of zidovudine dose on the formation of intracellular phosphorylated metabolites.
Back, DJ; Barry, MG; Breckenridge, AM; Gibbons, SE; Hoggard, PG; Khoo, SH; Veal, GJ; Wilkins, EG; Williams, O, 1996
)
0.29
" Data including demographic information, immunological markers (CD2+, CD3+, CD4+, CD5+/19+, CD8+, CD16+, CD19+, CD38+/8+ lymphocytes), hematologic function (absolute neutrophil count, white blood cell with differential, hemoglobin, and red blood cell count), concurrent medications, and dosage regimens were obtained."( Phosphorylated zidovudine concentrations in mononuclear cells in pediatric patients with human immunodeficiency virus infections.
Baker, RC; Brady, MT; Hunkler, JA; McOwen, NM; Nahata, MC; Sobol, BJ; Wintermeyer, SM, 1997
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidylate kinaseMycobacterium tuberculosis H37RvKi10.00004.50008.500010.0000AID210897; AID210904; AID211055; AID635863
[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 1Kd4.18910.00062.40599.8000AID341978; AID432590; AID432591; AID432592; AID432593; AID432599
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine kinase, cytosolicHomo sapiens (human)Km12.00000.29002.27675.0000AID210900
Thymidylate kinaseHomo sapiens (human)Km7.60005.00007.725010.0000AID325367
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Activity24.25000.00091.30738.0000AID341976; AID341977; AID341991; AID341992
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Km1,225.00000.07001.91446.9000AID341979; AID341980; AID341981; AID341982
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

Processvia Protein(s)Taxonomy
nucleobase-containing compound metabolic processThymidine kinase, cytosolicHomo sapiens (human)
deoxyribonucleoside monophosphate biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine metabolic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
protein homotetramerizationThymidine kinase, cytosolicHomo sapiens (human)
DNA synthesis involved in mitotic DNA replicationThymidine kinase, cytosolicHomo sapiens (human)
dTDP biosynthetic processThymidylate kinaseHomo sapiens (human)
dTTP biosynthetic processThymidylate kinaseHomo sapiens (human)
response to estrogenThymidylate kinaseHomo sapiens (human)
myoblast differentiationThymidylate kinaseHomo sapiens (human)
thymidine biosynthetic processThymidylate kinaseHomo sapiens (human)
response to cadmium ionThymidylate kinaseHomo sapiens (human)
nucleoside monophosphate phosphorylationThymidylate kinaseHomo sapiens (human)
cellular response to growth factor stimulusThymidylate kinaseHomo sapiens (human)
dUDP biosynthetic processThymidylate kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
thymidine kinase activityThymidine kinase, cytosolicHomo sapiens (human)
protein bindingThymidine kinase, cytosolicHomo sapiens (human)
ATP bindingThymidine kinase, cytosolicHomo sapiens (human)
zinc ion bindingThymidine kinase, cytosolicHomo sapiens (human)
identical protein bindingThymidine kinase, cytosolicHomo sapiens (human)
thymidylate kinase activityThymidylate kinaseHomo sapiens (human)
ATP bindingThymidylate kinaseHomo sapiens (human)
nucleoside diphosphate kinase activityThymidylate kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
nucleusThymidine kinase, cytosolicHomo sapiens (human)
cytosolThymidine kinase, cytosolicHomo sapiens (human)
mitochondrial matrixThymidylate kinaseHomo sapiens (human)
cytosolThymidylate kinaseHomo sapiens (human)
mitochondrionThymidylate kinaseHomo sapiens (human)
nucleusThymidylate kinaseHomo sapiens (human)
cytoplasmThymidylate kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (66)

Assay IDTitleYearJournalArticle
AID432608Binding affinity to 200 nM wild type HIV1 LAI reverse transcriptase assessed as ATP-mediated excision of zidovudine-monophosphate from chain terminated DNA/DNA template/primer duplex at 100 uM2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID619511Cytotoxicity against human CEM-T4 cells assessed as cell viability after 7 days by MTT assay2011Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19
Aryl H-phosphonates 17: (N-aryl)phosphoramidates of pyrimidine nucleoside analogues and their synthesis, selected properties, and anti-HIV activity.
AID341983Ratio of Kcat to Km for HIV1 reverse transcriptase assessed as nucleotide excision activity in presence of 0.5 uM dCTP2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID74259In vitro inhibition of UDP-[3H]-GlcNAc import into the lumen of the Golgi membranes from rabbit liver homogenate.1996Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15
Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.
AID221371Concentration of external nucleoside in mouse brain1992Journal of medicinal chemistry, Aug-07, Volume: 35, Issue:16
Improved brain delivery of AZT using a glycosyl phosphotriester prodrug.
AID341976Inhibition of HIV1 reverse transcriptase assessed as dCTP level required to form 50% of binary enzyme complex formation with drug-terminated primer in posttranslocation state by site-specific foot printing assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID680358TP_TRANSPORTER: efflux in CEM-r1 cells1999Nature medicine, Sep, Volume: 5, Issue:9
MRP4: A previously unidentified factor in resistance to nucleoside-based antiviral drugs.
AID24894Half life evaluated in Culture Medium(CM)1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate-protecting groups: intracellular delivery of 3'-azido-2',3'-dideoxythymidine 5'-monophosphate.
AID432590Binding affinity to wild type HIV1 LAI reverse transcriptase assessed as ATP-mediated excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain at 100 uM by gel shift mobility assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432613Selectivity ratio of Kd for excision of zidovudine-monophosphate from chain terminated DNA/DNA template/primer duplex in 200 nM HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant to Kd for excision of zidovudine-monophosphate from chain terminated DNA2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID553326Ratio of kcat/km for human recombinant TMPK by Michaelis-Menten equation analysis2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Novel antiviral C5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates.
AID235817ratio of Ki (Km TMPKh / Ki TMPKmt) was determined2003Journal of medicinal chemistry, Aug-28, Volume: 46, Issue:18
3'-C-branched-chain-substituted nucleosides and nucleotides as potent inhibitors of Mycobacterium tuberculosis thymidine monophosphate kinase.
AID432605Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant assessed as ATP-mediated excision of zidovudine-monophosphate from chain terminated RNA/DNA template/primer duplex2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432607Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V/G333D mutant assessed as ATP-mediated excision of zidovudine-monophosphate from chain terminated RNA/DNA template/primer duplex2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432609Binding affinity to 200 nM HIV1 LAI reverse transcriptase M184V mutant assessed as ATP-mediated excision of zidovudine-monophosphate from chain terminated DNA/DNA template/primer duplex at 100 uM2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432601Selectivity ratio of Kd for excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain in HIV1 LAI reverse transcriptase M41L/L210W/T215Y/K65R mutant to Kd for excision of zidovudine-monophosphate terminated DNA/DNA template/prim2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID74253Inhibitory concentration at which there is accumulation of UDP-[3H]-GlcNAc in the lumen of the Golgi membranes.1996Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15
Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.
AID341977Inhibition of HIV1 reverse transcriptase assessed as dCTP level required to form 80% of binary enzyme complex formation with drug-terminated primer in posttranslocation state by site-specific foot printing assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID325367Activity for human recombinant TMP kinase2007Antimicrobial agents and chemotherapy, May, Volume: 51, Issue:5
Comparison of the phosphorylation of 4'-ethynyl 2',3'-dihydro-3'-deoxythymidine with that of other anti-human immunodeficiency virus thymidine analogs.
AID222817In Vitro detection by Gray and Whittaker method for the total internal nucleoside1992Journal of medicinal chemistry, Aug-07, Volume: 35, Issue:16
Improved brain delivery of AZT using a glycosyl phosphotriester prodrug.
AID91571Inhibition of 3' processing step useful in the integration of viral DNA into host cell DNA by inhibiting HIV integrase by compound2000Bioorganic & medicinal chemistry letters, Feb-07, Volume: 10, Issue:3
Recognition and inhibition of HIV integrase by a novel dinucleotide.
AID341980Activity of HIV1 reverse transcriptase assessed as nucleotide excision activity in presence of 10 uM dCTP2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID341987Ratio of Kcat/Km for HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant to Kcat/Km for wild-type reverse transcriptase assessed as nucleotide excision activity in presence of 0.5 uM dCTP2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID325368Ratio of Kcat to Km of human recombinant TMPK relative to D4TDP2007Antimicrobial agents and chemotherapy, May, Volume: 51, Issue:5
Comparison of the phosphorylation of 4'-ethynyl 2',3'-dihydro-3'-deoxythymidine with that of other anti-human immunodeficiency virus thymidine analogs.
AID341985Ratio of Kcat to Km for HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant assessed as nucleotide excision activity in presence of 0.5 uM dCTP2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID341978Binding affinity to ternary complex of HIV1 reverse transcriptase with primer/template in presence of dCTP substrate2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID432603Binding affinity to wild type HIV1 LAI reverse transcriptase assessed as ATP-mediated excision of zidovudine-monophosphate from chain terminated RNA/DNA template/primer duplex2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID221610In Vitro detection by Gray and Whittaker method for % of internalization by comparing with external nucleoside of 2000 nM/g1992Journal of medicinal chemistry, Aug-07, Volume: 35, Issue:16
Improved brain delivery of AZT using a glycosyl phosphotriester prodrug.
AID432606Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V mutant assessed as ATP-mediated excision of zidovudine-monophosphate from chain terminated RNA/DNA template/primer duplex2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432612Binding affinity to 200 nM HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V/G333D mutant assessed as ATP-mediated excision of zidovudine-monophosphate from chain terminated DNA/DNA template/primer duplex at 100 uM2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432593Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V mutant assessed as ATP-mediated excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain at 100 uM by gel shift mobility assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432599Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/K65R mutant assessed as ATP-mediated excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain at 100 uM by gel shift mobility assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432591Binding affinity to HIV1 LAI reverse transcriptase M184V mutant assessed as ATP-mediated excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain at 100 uM by gel shift mobility assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432597Selectivity ratio of Kd for excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain in HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V mutant to Kd for excision of zidovudine-monophosphate terminated DNA/DNA template/pri2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID341991Inhibition of HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant assessed as dCTP level required to form 50% of binary enzyme complex formation with drug-terminated primer in posttranslocation state by site-specific foot printing assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID432596Selectivity ratio of Kd for excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain in HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant to Kd for excision of zidovudine-monophosphate terminated DNA/DNA template/primer du2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID341979Activity of HIV1 reverse transcriptase assessed as nucleotide excision activity in presence of 0.5 uM dCTP2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID619513Antiviral activity against HIV1 infected in human CEM-T4 cells assessed as reduction in viral protein p24 production preincubated for 24 hrs measured after 8 days by MTT assay2011Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19
Aryl H-phosphonates 17: (N-aryl)phosphoramidates of pyrimidine nucleoside analogues and their synthesis, selected properties, and anti-HIV activity.
AID341990Ratio of Kcat/Km for HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant in presence of 0.5 uM dCTP to Kcat/Km for reverse transcriptase M41L/D67N/L210W/T215Y mutant in presence of 10 uM dCTP by nucleotide excision activity assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID24898Half life evaluated in Total Cell Extract(TCE).1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate-protecting groups: intracellular delivery of 3'-azido-2',3'-dideoxythymidine 5'-monophosphate.
AID341984Ratio of Kcat to Km for HIV1 reverse transcriptase assessed as nucleotide excision activity in presence of 10 uM dCTP2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID341981Activity of HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant assessed as nucleotide excision activity in presence of 0.5 uM dCTP2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID341989Ratio of Kcat/Km for HIV1 reverse transcriptase in presence of 0.5 uM dCTP to Kcat/Km for reverse transcriptase in presence of 10 uM dCTP by nucleotide excision activity assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID210900In Vitro inhibition of Thymidine Monophosphatase Kinase (TMPKh)2003Journal of medicinal chemistry, Aug-28, Volume: 46, Issue:18
3'-C-branched-chain-substituted nucleosides and nucleotides as potent inhibitors of Mycobacterium tuberculosis thymidine monophosphate kinase.
AID432598Selectivity ratio of Kd for excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain in HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V/G333D mutant to Kd for excision of zidovudine-monophosphate terminated DNA/DNA templa2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID210897In Vitro inhibition of Thymidine Monophosphatase Kinase of Mycobacterium tuberculosis (TMPKm)2003Journal of medicinal chemistry, Aug-28, Volume: 46, Issue:18
3'-C-branched-chain-substituted nucleosides and nucleotides as potent inhibitors of Mycobacterium tuberculosis thymidine monophosphate kinase.
AID619510Chemical stability of the compound in RPMI cell culture media assessed as half life at 2 mM2011Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19
Aryl H-phosphonates 17: (N-aryl)phosphoramidates of pyrimidine nucleoside analogues and their synthesis, selected properties, and anti-HIV activity.
AID635863Competitive inhibition of Mycobacterium tuberculosis TMPK expressed in Escherichia coli NM554 by coupled spectrophotometric assay2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Synthesis and inhibitory activity of thymidine analogues targeting Mycobacterium tuberculosis thymidine monophosphate kinase.
AID341992Inhibition of HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant assessed as dCTP level required to form 80% of binary enzyme complex formation with drug-terminated primer in posttranslocation state by site-specific foot printing assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID432610Binding affinity to 200 nM HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant assessed as ATP-mediated excision of zidovudine-monophosphate from chain terminated DNA/DNA template/primer duplex at 100 uM2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID91572Inhibition of strand transfer step useful in the integration of viral DNA into host cell DNA by inhibiting HIV integrase by compound2000Bioorganic & medicinal chemistry letters, Feb-07, Volume: 10, Issue:3
Recognition and inhibition of HIV integrase by a novel dinucleotide.
AID432602Selectivity ratio of Kd for excision of zidovudine-monophosphate from chain terminated DNA/DNA template/primer duplex in HIV1 LAI reverse transcriptase M41L/L210W/T215Y/K65R/G333D mutant to Kd for excision of zidovudine-monophosphate from chain terminated2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID210904Inhibitory activity against thymidine monophosphate kinase (TMPK) in Mycobacterium tuberculosis2003Bioorganic & medicinal chemistry letters, Sep-15, Volume: 13, Issue:18
Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID211055Compound was tested for binding affinity against Mycobacterium tuberculosis thymidine monophosphate kinase2002Bioorganic & medicinal chemistry letters, Oct-07, Volume: 12, Issue:19
Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID432611Binding affinity to 200 nM HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V mutant assessed as ATP-mediated excision of zidovudine-monophosphate from chain terminated DNA/DNA template/primer duplex at 100 uM2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432594Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V/G333D mutant assessed as ATP-mediated excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain at 100 uM by gel shift mobility assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID341982Activity of HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant assessed as nucleotide excision activity in presence of 10 uM dCTP2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID432595Selectivity ratio of Kd for excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain in HIV1 LAI reverse transcriptase M184V mutant to Kd for excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain 2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID341986Ratio of Kcat to Km for HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant assessed as nucleotide excision activity in presence of 10 uM dCTP2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID432592Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant assessed as ATP-mediated excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain at 100 uM by gel shift mobility assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID619514Selectivity index, ratio of CC50 for human CEM-T4 cells to EC50 for HIV1 infected human CEM-T4 cells2011Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19
Aryl H-phosphonates 17: (N-aryl)phosphoramidates of pyrimidine nucleoside analogues and their synthesis, selected properties, and anti-HIV activity.
AID341988Ratio of Kcat/Km for HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant to Kcat/Km for wild-type reverse transcriptase assessed as nucleotide excision activity in presence of 10 uM dCTP2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID74256The compound was tested for extent of UDP-[3H]-GlcNAc accumulation into the lumen of the Golgi membranes.1996Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15
Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.
AID432600Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/K65R/G333D mutant assessed as ATP-mediated excision of zidovudine-monophosphate terminated DNA/DNA template/primer duplex chain at 100 uM by gel shift mobility assay2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432604Binding affinity to HIV1 LAI reverse transcriptase M184V mutant assessed as ATP-mediated excision of zidovudine-monophosphate from chain terminated RNA/DNA template/primer duplex at 100 uM2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432614Selectivity ratio of Kd for excision of zidovudine-monophosphate from chain terminated DNA/DNA template/primer duplex in 200 nM HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant to Kd for excision of zidovudine-monophosphate from chain terminated DNA2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (98)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (1.02)18.7374
1990's52 (53.06)18.2507
2000's39 (39.80)29.6817
2010's6 (6.12)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.14

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 Index12.14 (24.57)
Research Supply Index4.69 (2.92)
Research Growth Index6.83 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.14)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (1.89%)5.53%
Reviews1 (0.94%)6.00%
Case Studies1 (0.94%)4.05%
Observational0 (0.00%)0.25%
Other102 (96.23%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]