Page last updated: 2024-09-23

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

Description

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

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]

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]

Research Highlights

Safety/Toxicity (5)

ArticleYear
Phosphorylation of thymidine and AZT in heart mitochondria: elucidation of a novel mechanism of AZT cardiotoxicity.
Cardiovascular toxicology, Volume: 4, Issue: 2
2004
Pro-oxidant properties and cytotoxicity of AZT-monophosphate and AZT.
Cardiovascular toxicology, Volume: 4, Issue: 2
2004
3'-Azido-3'-deoxythymidine potently inhibits protein glycosylation. A novel mechanism for AZT cytotoxicity.
The Journal of biological chemistry, May-20, Volume: 269, Issue: 20
1994
3'-Azido-3'-deoxythymidine cytotoxicity and metabolism in the human colon tumor cell line HCT-8.
Biochemical pharmacology, Nov-01, Volume: 48, Issue: 9
1994
Cytotoxicity of 3'-azido-3'-deoxythymidine correlates with 3'-azidothymidine-5'-monophosphate (AZTMP) levels, whereas anti-human immunodeficiency virus (HIV) activity correlates with 3'-azidothymidine-5'-triphosphate (AZTTP) levels in cultured CEM T-lymph
Biochemical pharmacology, Mar-15, Volume: 49, Issue: 6
1995
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (3)

ArticleYear
Intracellular metabolism and pharmacokinetics of 5'-hydrogenphosphonate of 3'-azido-2',3'-dideoxythymidine, a prodrug of 3'-azido-2',3'-dideoxythymidine.
Antiviral research, Volume: 63, Issue: 2
2004
Pharmacokinetics of zidovudine phosphorylation in human immunodeficiency virus-positive thai patients and healthy volunteers.
Antimicrobial agents and chemotherapy, Volume: 44, Issue: 7
2000
Systemic pharmacokinetics and cellular pharmacology of zidovudine in human immunodeficiency virus type 1-infected women and newborn infants.
The Journal of infectious diseases, Volume: 180, Issue: 6
1999
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (5)

ArticleYear
Phosphorylated zidovudine concentrations in mononuclear cells in pediatric patients with human immunodeficiency virus infections.
Pediatric AIDS and HIV infection, Volume: 8, Issue: 2
1997
Low-dose, sublingual AZT-monophosphate therapy for HIV+ patients?
Medical hypotheses, Volume: 56, Issue: 3
2001
The effect of zidovudine dose on the formation of intracellular phosphorylated metabolites.
AIDS (London, England), Volume: 10, Issue: 12
1996
In vitro measurement of phosphorylated zidovudine in peripheral blood leucocytes.
Therapeutic drug monitoring, Volume: 12, Issue: 5
1990
Intracellular zidovudine (ZDV) and ZDV phosphates as measured by a validated combined high-pressure liquid chromatography-radioimmunoassay procedure.
Antimicrobial agents and chemotherapy, Volume: 36, Issue: 11
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]