Compounds > 3'-azido-3'-deoxythymidine 5'phosphate

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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 Source	ID
PubMed CID	65374
CHEMBL ID	257695
SCHEMBL ID	15094301
MeSH ID	M0160359

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

Excerpt	Reference	Relevance
" 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

Excerpt	Relevance	Reference
"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

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Thymidylate kinase	Mycobacterium tuberculosis H37Rv	Ki	10.0000	4.5000	8.5000	10.0000	AID210897; AID210904; AID211055; AID635863
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Reverse transcriptase/RNaseH	Human immunodeficiency virus 1	Kd	4.1891	0.0006	2.4059	9.8000	AID341978; AID432590; AID432591; AID432592; AID432593; AID432599
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Thymidine kinase, cytosolic	Homo sapiens (human)	Km	12.0000	0.2900	2.2767	5.0000	AID210900
Thymidylate kinase	Homo sapiens (human)	Km	7.6000	5.0000	7.7250	10.0000	AID325367
Reverse transcriptase/RNaseH	Human immunodeficiency virus 1	Activity	24.2500	0.0009	1.3073	8.0000	AID341976; AID341977; AID341991; AID341992
Reverse transcriptase/RNaseH	Human immunodeficiency virus 1	Km	1,225.0000	0.0700	1.9144	6.9000	AID341979; AID341980; AID341981; AID341982
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

Process	via Protein(s)	Taxonomy
nucleobase-containing compound metabolic process	Thymidine kinase, cytosolic	Homo sapiens (human)
deoxyribonucleoside monophosphate biosynthetic process	Thymidine kinase, cytosolic	Homo sapiens (human)
thymidine metabolic process	Thymidine kinase, cytosolic	Homo sapiens (human)
thymidine biosynthetic process	Thymidine kinase, cytosolic	Homo sapiens (human)
protein homotetramerization	Thymidine kinase, cytosolic	Homo sapiens (human)
DNA synthesis involved in mitotic DNA replication	Thymidine kinase, cytosolic	Homo sapiens (human)
dTDP biosynthetic process	Thymidylate kinase	Homo sapiens (human)
dTTP biosynthetic process	Thymidylate kinase	Homo sapiens (human)
response to estrogen	Thymidylate kinase	Homo sapiens (human)
myoblast differentiation	Thymidylate kinase	Homo sapiens (human)
thymidine biosynthetic process	Thymidylate kinase	Homo sapiens (human)
response to cadmium ion	Thymidylate kinase	Homo sapiens (human)
nucleoside monophosphate phosphorylation	Thymidylate kinase	Homo sapiens (human)
cellular response to growth factor stimulus	Thymidylate kinase	Homo sapiens (human)
dUDP biosynthetic process	Thymidylate kinase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Process	via Protein(s)	Taxonomy
thymidine kinase activity	Thymidine kinase, cytosolic	Homo sapiens (human)
protein binding	Thymidine kinase, cytosolic	Homo sapiens (human)
ATP binding	Thymidine kinase, cytosolic	Homo sapiens (human)
zinc ion binding	Thymidine kinase, cytosolic	Homo sapiens (human)
identical protein binding	Thymidine kinase, cytosolic	Homo sapiens (human)
thymidylate kinase activity	Thymidylate kinase	Homo sapiens (human)
ATP binding	Thymidylate kinase	Homo sapiens (human)
nucleoside diphosphate kinase activity	Thymidylate kinase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Process	via Protein(s)	Taxonomy
nucleus	Thymidine kinase, cytosolic	Homo sapiens (human)
cytosol	Thymidine kinase, cytosolic	Homo sapiens (human)
mitochondrial matrix	Thymidylate kinase	Homo sapiens (human)
cytosol	Thymidylate kinase	Homo sapiens (human)
mitochondrion	Thymidylate kinase	Homo sapiens (human)
nucleus	Thymidylate kinase	Homo sapiens (human)
cytoplasm	Thymidylate kinase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (66)

Assay ID	Title	Year	Journal	Article
AID432608	Binding 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 uM	2008	Antimicrobial 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.
AID619511	Cytotoxicity against human CEM-T4 cells assessed as cell viability after 7 days by MTT assay	2011	Journal 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.
AID341983	Ratio of Kcat to Km for HIV1 reverse transcriptase assessed as nucleotide excision activity in presence of 0.5 uM dCTP	2007	Antimicrobial 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.
AID74259	In vitro inhibition of UDP-[3H]-GlcNAc import into the lumen of the Golgi membranes from rabbit liver homogenate.	1996	Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15	Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.
AID221371	Concentration of external nucleoside in mouse brain	1992	Journal of medicinal chemistry, Aug-07, Volume: 35, Issue:16	Improved brain delivery of AZT using a glycosyl phosphotriester prodrug.
AID341976	Inhibition 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 assay	2007	Antimicrobial 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.
AID680358	TP_TRANSPORTER: efflux in CEM-r1 cells	1999	Nature medicine, Sep, Volume: 5, Issue:9	MRP4: A previously unidentified factor in resistance to nucleoside-based antiviral drugs.
AID24894	Half life evaluated in Culture Medium(CM)	1995	Journal 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.
AID432590	Binding 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 assay	2008	Antimicrobial 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.
AID432613	Selectivity 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 DNA	2008	Antimicrobial 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.
AID553326	Ratio of kcat/km for human recombinant TMPK by Michaelis-Menten equation analysis	2011	Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1	Novel antiviral C5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates.
AID235817	ratio of Ki (Km TMPKh / Ki TMPKmt) was determined	2003	Journal 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.
AID432605	Binding 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 duplex	2008	Antimicrobial 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.
AID432607	Binding 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 duplex	2008	Antimicrobial 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.
AID432609	Binding 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 uM	2008	Antimicrobial 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.
AID432601	Selectivity 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/prim	2008	Antimicrobial 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.
AID74253	Inhibitory concentration at which there is accumulation of UDP-[3H]-GlcNAc in the lumen of the Golgi membranes.	1996	Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15	Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.
AID341977	Inhibition 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 assay	2007	Antimicrobial 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.
AID325367	Activity for human recombinant TMP kinase	2007	Antimicrobial 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.
AID222817	In Vitro detection by Gray and Whittaker method for the total internal nucleoside	1992	Journal of medicinal chemistry, Aug-07, Volume: 35, Issue:16	Improved brain delivery of AZT using a glycosyl phosphotriester prodrug.
AID91571	Inhibition of 3' processing step useful in the integration of viral DNA into host cell DNA by inhibiting HIV integrase by compound	2000	Bioorganic & medicinal chemistry letters, Feb-07, Volume: 10, Issue:3	Recognition and inhibition of HIV integrase by a novel dinucleotide.
AID341980	Activity of HIV1 reverse transcriptase assessed as nucleotide excision activity in presence of 10 uM dCTP	2007	Antimicrobial 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.
AID341987	Ratio 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 dCTP	2007	Antimicrobial 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.
AID325368	Ratio of Kcat to Km of human recombinant TMPK relative to D4TDP	2007	Antimicrobial 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.
AID341985	Ratio of Kcat to Km for HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant assessed as nucleotide excision activity in presence of 0.5 uM dCTP	2007	Antimicrobial 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.
AID341978	Binding affinity to ternary complex of HIV1 reverse transcriptase with primer/template in presence of dCTP substrate	2007	Antimicrobial 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.
AID432603	Binding affinity to wild type HIV1 LAI reverse transcriptase assessed as ATP-mediated excision of zidovudine-monophosphate from chain terminated RNA/DNA template/primer duplex	2008	Antimicrobial 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.
AID221610	In Vitro detection by Gray and Whittaker method for % of internalization by comparing with external nucleoside of 2000 nM/g	1992	Journal of medicinal chemistry, Aug-07, Volume: 35, Issue:16	Improved brain delivery of AZT using a glycosyl phosphotriester prodrug.
AID432606	Binding 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 duplex	2008	Antimicrobial 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.
AID432612	Binding 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 uM	2008	Antimicrobial 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.
AID432593	Binding 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 assay	2008	Antimicrobial 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.
AID432599	Binding 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 assay	2008	Antimicrobial 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.
AID432591	Binding 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 assay	2008	Antimicrobial 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.
AID432597	Selectivity 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/pri	2008	Antimicrobial 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.
AID341991	Inhibition 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 assay	2007	Antimicrobial 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.
AID432596	Selectivity 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 du	2008	Antimicrobial 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.
AID341979	Activity of HIV1 reverse transcriptase assessed as nucleotide excision activity in presence of 0.5 uM dCTP	2007	Antimicrobial 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.
AID619513	Antiviral 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 assay	2011	Journal 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.
AID341990	Ratio 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 assay	2007	Antimicrobial 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.
AID24898	Half life evaluated in Total Cell Extract(TCE).	1995	Journal 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.
AID341984	Ratio of Kcat to Km for HIV1 reverse transcriptase assessed as nucleotide excision activity in presence of 10 uM dCTP	2007	Antimicrobial 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.
AID341981	Activity of HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant assessed as nucleotide excision activity in presence of 0.5 uM dCTP	2007	Antimicrobial 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.
AID341989	Ratio 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 assay	2007	Antimicrobial 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.
AID210900	In Vitro inhibition of Thymidine Monophosphatase Kinase (TMPKh)	2003	Journal 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.
AID432598	Selectivity 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 templa	2008	Antimicrobial 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.
AID210897	In Vitro inhibition of Thymidine Monophosphatase Kinase of Mycobacterium tuberculosis (TMPKm)	2003	Journal 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.
AID619510	Chemical stability of the compound in RPMI cell culture media assessed as half life at 2 mM	2011	Journal 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.
AID635863	Competitive inhibition of Mycobacterium tuberculosis TMPK expressed in Escherichia coli NM554 by coupled spectrophotometric assay	2011	Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24	Synthesis and inhibitory activity of thymidine analogues targeting Mycobacterium tuberculosis thymidine monophosphate kinase.
AID341992	Inhibition 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 assay	2007	Antimicrobial 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.
AID432610	Binding 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 uM	2008	Antimicrobial 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.
AID91572	Inhibition of strand transfer step useful in the integration of viral DNA into host cell DNA by inhibiting HIV integrase by compound	2000	Bioorganic & medicinal chemistry letters, Feb-07, Volume: 10, Issue:3	Recognition and inhibition of HIV integrase by a novel dinucleotide.
AID432602	Selectivity 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 terminated	2008	Antimicrobial 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.
AID210904	Inhibitory activity against thymidine monophosphate kinase (TMPK) in Mycobacterium tuberculosis	2003	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 13, Issue:18	Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID211055	Compound was tested for binding affinity against Mycobacterium tuberculosis thymidine monophosphate kinase	2002	Bioorganic & 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.
AID432611	Binding 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 uM	2008	Antimicrobial 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.
AID432594	Binding 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 assay	2008	Antimicrobial 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.
AID341982	Activity of HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant assessed as nucleotide excision activity in presence of 10 uM dCTP	2007	Antimicrobial 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.
AID432595	Selectivity 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	2008	Antimicrobial 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.
AID341986	Ratio of Kcat to Km for HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant assessed as nucleotide excision activity in presence of 10 uM dCTP	2007	Antimicrobial 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.
AID432592	Binding 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 assay	2008	Antimicrobial 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.
AID619514	Selectivity index, ratio of CC50 for human CEM-T4 cells to EC50 for HIV1 infected human CEM-T4 cells	2011	Journal 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.
AID341988	Ratio 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 dCTP	2007	Antimicrobial 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.
AID74256	The compound was tested for extent of UDP-[3H]-GlcNAc accumulation into the lumen of the Golgi membranes.	1996	Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15	Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.
AID432600	Binding 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 assay	2008	Antimicrobial 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.
AID432604	Binding 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 uM	2008	Antimicrobial 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.
AID432614	Selectivity 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 DNA	2008	Antimicrobial 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)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (1.02)	18.7374
1990's	52 (53.06)	18.2507
2000's	39 (39.80)	29.6817
2010's	6 (6.12)	24.3611
2020's	0 (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.

Metric	This Compound (vs All)
Research Demand Index	12.14 (24.57)
Research Supply Index	4.69 (2.92)
Research Growth Index	6.83 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.14)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	2 (1.89%)	5.53%
Reviews	1 (0.94%)	6.00%
Case Studies	1 (0.94%)	4.05%
Observational	0 (0.00%)	0.25%
Other	102 (96.23%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
adenine [no description available]	2.41	2	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
aconitic acid Aconitic Acid: A tricarboxylic acid with the formula (COOH)-CH2-C(COOH)=CH-COOH.. aconitic acid : A tricarboxylic acid that is prop-1-ene substituted by carboxy groups at positions 1, 2 and 3.	2	1	0	tricarboxylic acid
4-aminopyridine [no description available]	2.06	1	0	aminopyridine; aromatic amine	avicide; orphan drug; potassium channel blocker
foscarnet Foscarnet: An antiviral agent used in the treatment of cytomegalovirus retinitis. Foscarnet also shows activity against human herpesviruses and HIV.. phosphonoformic acid : Phosphoric acid in which one of the hydroxy groups is replaced by a carboxylic acid group. It is used as the trisodium salt as an antiviral agent in the treatment of cytomegalovirus retinitis (CMV retinitis, an inflamation of the retina that can lead to blindness) and as an alternative to ganciclovir for AIDS patients who require concurrent antiretroviral therapy but are unable to tolerate ganciclovir due to haematological toxicity.	2.01	1	0	carboxylic acid; one-carbon compound; phosphonic acids	antiviral drug; geroprotector; HIV-1 reverse transcriptase inhibitor; sodium-dependent Pi-transporter inhibitor
molsidomine Molsidomine: A morpholinyl sydnone imine ethyl ester, having a nitrogen in place of the keto oxygen. It acts as NITRIC OXIDE DONORS and is a vasodilator that has been used in ANGINA PECTORIS.. molsidomine : A member of the class of oxadiazoles that is 1,2,3-oxadiazole substituted by morpholin-4-yl and (ethoxycarbonyl)azanidyl groups at positions 3 and 5, respectively. It is used as a vasodilator drug for the treatment of myocardial ischemic syndrome and congestive heart failure.	2.02	1	0	ethyl ester; morpholines; oxadiazole; zwitterion	antioxidant; apoptosis inhibitor; cardioprotective agent; nitric oxide donor; vasodilator agent
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	1.98	1	0	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
nevirapine Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.	2.01	1	0	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor
linsidomine linsidomine: RN given refers to parent cpd; structure	2.02	1	0	morpholines
thymidine [no description available]	4.61	8	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	2.69	3	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.03	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
uridine monophosphate Uridine Monophosphate: 5'-Uridylic acid. A uracil nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.. uridine 5'-monophosphate : A pyrimidine ribonucleoside 5'-monophosphate having uracil as the nucleobase.	1.98	1	0	pyrimidine ribonucleoside 5'-monophosphate; uridine 5'-phosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
aniline [no description available]	2.06	1	0	anilines; primary arylamine
cytidine monophosphate Cytidine Monophosphate: Cytidine (dihydrogen phosphate). A cytosine nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.. cytidine 5'-monophosphate : A pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase.	2.39	2	0	cytidine 5'-phosphate; pyrimidine ribonucleoside 5'-monophosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
cytidine diphosphate Cytidine Diphosphate: Cytidine 5'-(trihydrogen diphosphate). A cytosine nucleotide containing two phosphate groups esterified to the sugar moiety. Synonyms: CRPP; cytidine pyrophosphate.	1.99	1	0	cytidine 5'-phosphate; pyrimidine ribonucleoside 5'-diphosphate	Escherichia coli metabolite; mouse metabolite
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	1.98	1	0	lactose
cytidine triphosphate Cytidine Triphosphate: Cytidine 5'-(tetrahydrogen triphosphate). A cytosine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.03	1	0	cytidine 5'-phosphate; pyrimidine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite
trifluridine Trifluridine: An antiviral derivative of THYMIDINE used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis due to HERPES SIMPLEX virus. (From Martindale, The Extra Pharmacopoeia, 30th ed, p557). trifluridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-trifluoromethyluracil as the nucleobase. An antiviral drug used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis.	2.01	1	0	nucleoside analogue; organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; EC 2.1.1.45 (thymidylate synthase) inhibitor
4-anisidine 4-anisidine: RN given refers to parent cpd. p-anisidine : A substituted aniline that is aniline in which the hydrogen para to the amino group has been replaced by a methoxy group. It is used as a reagent for the detection of oxidation products such as aldehydes and ketones in fats and oils.	2.06	1	0	methoxybenzenes; primary amino compound; substituted aniline	genotoxin; reagent
4-chloroaniline 4-chloroaniline: RN given refers to parent cpd; structure. 4-chloroaniline : A chloroaniline in which the chloro atom is para to the aniline amino group.	2.06	1	0	chloroaniline; monochlorobenzenes
fluorodeoxyuridylate Fluorodeoxyuridylate: 5-Fluoro-2'-deoxyuridylate. An inhibitor of thymidylate synthetase. Formed from 5-fluorouracil or 5-fluorodeoxyuridine.	2.42	2	0	pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
5-fluorouridine [no description available]	2.01	1	0	organofluorine compound; uridines	mutagen
thymidine monophosphate Thymidine Monophosphate: 5-Thymidylic acid. A thymine nucleotide containing one phosphate group esterified to the deoxyribose moiety.. dTMP : The neutral species of thymidine 5'-monophosphate (2'-deoxythymidine 5'-monophosphate).	4.08	15	0	thymidine 5'-monophosphate	fundamental metabolite
3-aminopyridine [no description available]	2.06	1	0
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	2.06	1	0
uridine diphosphate n-acetylglucosamine Uridine Diphosphate N-Acetylglucosamine: Serves as the biological precursor of insect chitin, of muramic acid in bacterial cell walls, and of sialic acids in mammalian glycoproteins.	1.98	1	0
deoxycytidine monophosphate Deoxycytidine Monophosphate: Deoxycytidine (dihydrogen phosphate). A deoxycytosine nucleotide containing one phosphate group esterified to the deoxyribose moiety in the 2'-,3'- or 5- positions.. 2'-deoxycytosine 5'-monophosphate : A pyrimidine 2'-deoxyribonucleoside 5'-monophosphate having cytosine as the nucleobase.	2.06	1	0	2'-deoxycytidine phosphate; pyrimidine 2'-deoxyribonucleoside 5'-monophosphate	Escherichia coli metabolite; mouse metabolite
uridine diphosphate galactose Uridine Diphosphate Galactose: A nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. Serves as a source of galactose in the synthesis of lipopolysaccharides, cerebrosides, and lactose.. UDP-alpha-D-galactose : A UDP-D-galactose in which the anomeric centre of the galactose moiety has alpha-configuration.	1.98	1	0	UDP-D-galactose	mouse metabolite
stavudine Stavudine: A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.. stavudine : A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase	3.1	5	0	dihydrofuran; nucleoside analogue; organic molecular entity	antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
doxifluridine doxifluridine : A pyrimidine 5'-deoxyribonucleoside that is 5-fluorouridine in which the hydroxy group at the 5' position is replaced by a hydrogen. It is an oral prodrug of the antineoplastic agent 5-fluorouracil. Designed to circumvent the rapid degradation of 5-fluorouracil by dihydropyrimidine dehydrogenase in the gut wall, it is converted into 5-fluorouracil in the presence of pyrimidine nucleoside phosphorylase.	2.01	1	0	organofluorine compound; pyrimidine 5'-deoxyribonucleoside	antimetabolite; antineoplastic agent; prodrug
mannose mannopyranose : The pyranose form of mannose.	1.97	1	0	D-aldohexose; D-mannose; mannopyranose	metabolite
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	1.98	1	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.03	1	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
alovudine [no description available]	2.01	1	0	pyrimidine 2',3'-dideoxyribonucleoside
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	10.27	92	2	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
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.	2.7	3	0	6-aminopurines; ether; phosphonic acids	antiviral drug; DNA synthesis inhibitor; drug metabolite; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent
cidofovir anhydrous Cidofovir: An acyclic nucleoside phosphonate that acts as a competitive inhibitor of viral DNA polymerases. It is used in the treatment of RETINITIS caused by CYTOMEGALOVIRUS INFECTIONS and may also be useful for treating HERPESVIRUS INFECTIONS.. cidofovir anhydrous : Cytosine substituted at the 1 position by a 3-hydroxy-2-(phosphonomethoxy)propyl group (S configuration). A nucleoside analogue, it is an injectable antiviral used for the treatment of cytomegalovirus (CMV) retinitis in AIDS patients.	2.06	1	0	phosphonic acids; pyrimidone	anti-HIV agent; antineoplastic agent; antiviral drug; photosensitizing agent
lamivudine [no description available]	2.44	2	0	monothioacetal; nucleoside analogue; oxacycle; primary alcohol	allergen; anti-HBV agent; antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor; prodrug
thymidine 5'-triphosphate thymidine 5'-triphosphate: RN given refers to parent cpd. dTTP : A thymidine phosphate having a triphosphate group at the 5'-position.	2.04	1	0	pyrimidine 2'-deoxyribonucleoside 5'-triphosphate; thymidine phosphate	Escherichia coli metabolite; mouse metabolite
thymine arabinoside thymine arabinoside: selectively inhibits replication of herpes simplex virus	2.01	1	0	N-glycosyl compound
2'-deoxyuridylic acid 2'-deoxyuridylic acid: RN given refers to parent cpd	2.93	4	0	deoxyuridine phosphate; pyrimidine 2'-deoxyribonucleoside 5'-monophosphate	Escherichia coli metabolite; metabolite; mouse metabolite
2'-deoxycytidine 5'-triphosphate 2'-deoxycytidine 5'-triphosphate: RN given refers to unlabeled parent cpd	2.04	1	0	2'-deoxycytidine phosphate; pyrimidine 2'-deoxyribonucleoside 5'-triphosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
phosphoramidic acid phosphoramidic acid: urease inhibitor; RN given refers to parent cpd; structure; do not confuse with phosphoramidites, which are organophosphorus compounds	2.03	1	0	phosphoric acid derivative
2',3'-dideoxyadenosine triphosphate [no description available]	2.03	1	0	purine deoxyribonucleoside triphosphate
5'-amino-2',5'-dideoxythymidine 5'-amino-5'-deoxythymidine: RN given refers to parent cpd	2.01	1	0
2',3'-dideoxyadenosine 5'-phosphate [no description available]	2.71	3	0
4-nitrobenzylthioinosine 4-nitrobenzylthioinosine: inhibitor of nucleoside transport; acts on ENT1	1.97	1	0	purine nucleoside
edoxudin [no description available]	2.01	1	0	pyrimidine 2'-deoxyribonucleoside
zidovudine triphosphate [no description available]	7.44	28	1
bromodeoxyuridylate bromodeoxyuridylate: RN given refers to parent cpd	2.72	3	0
3'-amino-2',3'-dideoxythymidine [no description available]	2.01	1	0
2'-fluorothymidine [no description available]	2.01	1	0
uridine diphosphate galactosamine uridine diphosphate galactosamine: isolated from Bacillus megaterium; intermediate in the biosynthesis of galactosamine-6-phosphate polymer. UDP-alpha-D-galactosamine : A UDP-amino sugar having alpha-D-galactosamine as the amino-sugar component.	1.99	1	0	UDP-amino sugar
3'-amino-3'-deoxythymidine 5'-monophosphate [no description available]	2.92	4	0
thymidine 5'-diphosphate thymidine 5'-diphosphate: see also record for thymidine 3',5'-diphosphate, RN 2863-04-9. dTDP : A thymidine phosphate having a diphosphate group at the 5'-position.	2.03	1	0	pyrimidine 2'-deoxyribonucleoside 5'-diphosphate; thymidine phosphate	Escherichia coli metabolite; mouse metabolite
udp-glucosamine UDP-glucosamine: RN given refers to (alpha)-isomer. UDP-alpha-D-glucosamine : A UDP-amino sugar having alpha-D-glucosamine as the amino-sugar component.	1.99	1	0	UDP-amino sugar
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2.41	2	0	divalent inorganic anion; phosphite ion
5'-(1,4-dihydro-1-methyl-3-pyridinylcarbonyl)-3'-azido-3'-deoxythymidine 5'-(1,4-dihydro-1-methyl-3-pyridinylcarbonyl)-3'-azido-3'-deoxythymidine: structure given in first source	2.02	1	0
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	2.02	1	0
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	1.98	1	0	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
abacavir abacavir: a carbocyclic nucleoside with potent selective anti-HIV activity. abacavir : A 2,6-diaminopurine that is (1S)-cyclopent-2-en-1-ylmethanol in which the pro-R hydrogen at the 4-position is substituted by a 2-amino-6-(cyclopropylamino)-9H-purin-9-yl group. A nucleoside analogue reverse transcriptase inhibitor (NRTI) with antiretroviral activity against HIV, it is used (particularly as the sulfate) with other antiretrovirals in combination therapy of HIV infection.	2.03	1	0	2,6-diaminopurines	antiviral drug; drug allergen; HIV-1 reverse transcriptase inhibitor
brivudine brivudine: anti-herpes agent	2.06	1	0
cytidine monophosphate n-acetylneuraminic acid Cytidine Monophosphate N-Acetylneuraminic Acid: A nucleoside monophosphate sugar which donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein.. CMP-N-acetyl-beta-neuraminic acid : A nucleotide sugar used as a donor by glycosyltransferases for the synthesis of sugar chains	2.39	2	0	CMP-N-acyl-beta-neuraminic acid	mouse metabolite
5-iodo-2'-deoxyuridine 5'-monophosphate iododeoxyuridylate: RN given refers to parent cpd	2.42	2	0
lamivudine triphosphate [no description available]	2.44	2	0
zidovudine triphosphate [no description available]	6.54	11	1
tenofovir tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.	2.73	3	0	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	2.69	3	0	diphosphate ion
thioinosine Thioinosine: Sulfhydryl analog of INOSINE that inhibits nucleoside transport across erythrocyte plasma membranes, and has immunosuppressive properties. It has been used similarly to MERCAPTOPURINE in the treatment of leukemia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p503)	1.97	1	0
3'-azido-2',3'-dideoxyuridine 3'-azido-2',3'-dideoxyuridine: structure given in first source	1.97	1	0
5-(2-bromovinyl)-2'-deoxyuridylate 5-(2-bromovinyl)-2'-deoxyuridylate: RN given refers to cpd without isomeric designation	1.99	1	0
3'-azido-3'-deoxy-5'-o-beta-glucopyranuronosylthymidine 3'-azido-3'-deoxy-5'-O-beta-glucopyranuronosylthymidine: major metabolite of zidovudine	1.98	1	0	pyrimidine 2',3'-dideoxyribonucleoside
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	2.06	1	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
2'-deoxyguanosine 5'-phosphate 2'-deoxyguanosine 5'-phosphate: RN given refers to parent cpd.. 2'-deoxyguanosine 5'-monophosphate : A purine 2'-deoxyribonucleoside 5'-monophosphate having guanine as the nucleobase.	2.05	1	0	deoxyguanosine phosphate; guanyl deoxyribonucleotide; purine 2'-deoxyribonucleoside 5'-monophosphate	Escherichia coli metabolite; mouse metabolite
inosine triphosphate Inosine Triphosphate: Inosine 5'-(tetrahydrogen triphosphate). An inosine nucleotide containing three phosphate groups esterified to the sugar moiety. Synonym: IRPPP.	1.99	1	0	inosine phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
ganciclovir [no description available]	2.06	1	0	2-aminopurines; oxopurine	antiinfective agent; antiviral drug

Condition	Relationship Strength	Studies	Trials
Koch's Disease [description not available]	2.06	1	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	2.06	1	0
HIV Coinfection [description not available]	5.89	13	2
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).	5.89	13	2
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	3.11	5	0
AIDS-Associated Lymphoma [description not available]	2.01	1	0
Lymphoma, AIDS-Related B-cell lymphoid tumors that occur in association with AIDS. Patients often present with an advanced stage of disease and highly malignant subtypes including BURKITT LYMPHOMA; IMMUNOBLASTIC LARGE-CELL LYMPHOMA; PRIMARY EFFUSION LYMPHOMA; and DIFFUSE, LARGE B-CELL, LYMPHOMA. The tumors are often disseminated in unusual extranodal sites and chromosomal abnormalities are frequently present. It is likely that polyclonal B-cell lymphoproliferation in AIDS is a complex result of EBV infection, HIV antigenic stimulation, and T-cell-dependent HIV activation.	2.01	1	0
Hematologic Malignancies [description not available]	2.02	1	0
Breast Cancer [description not available]	2.02	1	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.02	1	0
Hematologic Neoplasms Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.	2.02	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.71	3	0
Complications, Infectious Pregnancy [description not available]	2.42	2	0
Cancer of Colon [description not available]	1.98	1	0
Colonic Neoplasms Tumors or cancer of the COLON.	1.98	1	0
Acquired Immune Deficiency Syndrome [description not available]	3.77	2	1
Acquired Immunodeficiency Syndrome An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.	3.77	2	1
HIV Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.	3.37	7	0
AIDS Seroconversion [description not available]	2	1	0
Leukemia L 1210 [description not available]	1.97	1	0

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