Page last updated: 2024-09-23

thymidine 5'-triphosphate

Description

thymidine 5'-triphosphate: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dTTP : A thymidine phosphate having a triphosphate group at the 5'-position. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID64968
CHEMBL ID363559
CHEBI ID18077
SCHEMBL ID77831
MeSH IDM0082144

Synonyms (66)

Synonym
thymidine 5'-(tetrahydrogen triphosphate)
pppdt
2'-deoxythymidine triphosphate
CHEBI:18077 ,
thymidine-5'-triphosphate
dthd5'ppp
deoxy-ttp
5-ttp
2-deoxythymidine 5-triphosphate
5-methyl-dutp
thymidine, mono(tetrahydrogen triphosphate) (ester)
thymidine 5'-(tetrahydrogen triphosphate) (8ci,9ci)
2'-deoxythymidine 5'-triphosphate
ttp (nucleotide)
thymidine triphosphate (6ci)
thymidine 5-(tetrahydrogen triphosphate)
mono(tetrahydrogen triphosphate) (ester)
C00459
TTP ,
deoxythymidine triphosphate
365-08-2
thymidine 5'-triphosphate
thymidine triphosphate
dttp
deoxythymidine 5'-triphosphate
[hydroxy-[[(2r,3s,5r)-3-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy]phosphoryl] phosphono hydrogen phosphate
2'-dttp
5'-ttp
1ZM7
1H79
DB02452
1OE0
einecs 206-669-7
[hydroxy-[[(2r,3s,5r)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] phosphono hydrogen phosphate
2''-deoxythymidine triphosphate
5''-ttp
thymidine 5''-(tetrahydrogen triphosphate)
thymidine 5''-triphosphate
dthd5''ppp
bdbm50164648
CHEMBL363559 ,
A812848
18423-43-3
hydroxy-[hydroxy-[[(2s,5r)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy-oxo-phosphaniumyl]oxy-phosphoryl]oxy-oxo-phosphonium
qop4k539mu ,
unii-qop4k539mu
EPITOPE ID:149166
[(2r,3s,5r)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (hydroxy-phosphonooxyphosphoryl) hydrogen phosphate
5'-dttp
gtpl5505
SCHEMBL77831
NHVNXKFIZYSCEB-XLPZGREQSA-N
((2r,3s,5r)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
DTXSID30189998
thymidine 5' triphosphate
deoxy-thymidine triphosphate
thymidine mono(tetrahydrogen triphosphate)
Q303961
deoxythymidine-5'-triphosphate
D87932
thymidine5-(tetrahydrogentriphosphate)
thymidine-5'-triphosphoric acid = ttp
HY-138615
CS-0159314
{[hydroxy({[hydroxy({[(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}phosphonic acid
AKOS040758092

Roles (2)

RoleDescription
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
thymidine phosphate
pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (14)

thymidine 5'-triphosphate is involved in 14 pathway(s), involving a total of 223 unique proteins and 942 unique compounds

PathwayProteinsCompounds
Pyrimidine Metabolism2353
beta-Ureidopropionase Deficiency2353
UMP Synthase Deficiency (Orotic Aciduria)2353
Dihydropyrimidinase Deficiency2353
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)2353
Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis917
Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis 2917
Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis 3820
O-Antigen Building Blocks Biosynthesis922
Pyrimidine Deoxyribonucleosides Salvage815
Pyrimidine Nucleotides and Nucleosides metabolism ( Pyrimidine Nucleotides and Nucleosides metabolism )4549
ATP + dTDP = ADP + dTTP ( Pyrimidine Nucleotides and Nucleosides metabolism )74
Pyrimidine synthesis and deprivation pathway (COVID-19 Disease Maps)1329
Biochemical pathways: part I0466
Pyrimidine metabolism038

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Deoxynucleoside kinaseDrosophila melanogaster (fruit fly)IC50 (µMol)1,000.00001,000.00001,000.00001,000.0000AID977608
DNA polymerase betaHomo sapiens (human)IC50 (µMol)1.40001.40006.56679.0000AID1443139
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Ki0.06100.00031.552310.0000AID238445
[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)
Chain A, ANAEROBIC RIBONUCLEOTIDE-TRIPHOSPHATE REDUCTASE LARGE CHAINTequatrovirus T4Kd13.000013.000016.000019.0000AID977611
Chain A, ANAEROBIC RIBONUCLEOTIDE-TRIPHOSPHATE REDUCTASE LARGE CHAINTequatrovirus T4Kd13.000013.000016.000019.0000AID977611
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Kd34.50890.00062.40599.8000AID432585; AID432586; AID432587; AID432588; AID529694; AID529695; AID529696; AID529697; AID572771
[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)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Km2.43610.07001.91446.9000AID239745; AID239748; AID239749; AID239754; AID239763; AID239764; AID239772; AID239774; AID239775; AID563945; AID563946; AID563947; AID563948; AID563949; AID563950; AID563951; AID563952; AID711539
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
nucleotide-excision repair, DNA gap fillingDNA polymerase betaHomo sapiens (human)
in utero embryonic developmentDNA polymerase betaHomo sapiens (human)
DNA-templated DNA replicationDNA polymerase betaHomo sapiens (human)
DNA repairDNA polymerase betaHomo sapiens (human)
base-excision repairDNA polymerase betaHomo sapiens (human)
base-excision repair, gap-fillingDNA polymerase betaHomo sapiens (human)
pyrimidine dimer repairDNA polymerase betaHomo sapiens (human)
inflammatory responseDNA polymerase betaHomo sapiens (human)
DNA damage responseDNA polymerase betaHomo sapiens (human)
salivary gland morphogenesisDNA polymerase betaHomo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damageDNA polymerase betaHomo sapiens (human)
response to gamma radiationDNA polymerase betaHomo sapiens (human)
somatic hypermutation of immunoglobulin genesDNA polymerase betaHomo sapiens (human)
response to ethanolDNA polymerase betaHomo sapiens (human)
lymph node developmentDNA polymerase betaHomo sapiens (human)
spleen developmentDNA polymerase betaHomo sapiens (human)
homeostasis of number of cellsDNA polymerase betaHomo sapiens (human)
neuron apoptotic processDNA polymerase betaHomo sapiens (human)
response to hyperoxiaDNA polymerase betaHomo sapiens (human)
immunoglobulin heavy chain V-D-J recombinationDNA polymerase betaHomo sapiens (human)
DNA biosynthetic processDNA polymerase betaHomo sapiens (human)
double-strand break repair via nonhomologous end joiningDNA polymerase betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
damaged DNA bindingDNA polymerase betaHomo sapiens (human)
DNA-directed DNA polymerase activityDNA polymerase betaHomo sapiens (human)
DNA-(apurinic or apyrimidinic site) endonuclease activityDNA polymerase betaHomo sapiens (human)
protein bindingDNA polymerase betaHomo sapiens (human)
microtubule bindingDNA polymerase betaHomo sapiens (human)
lyase activityDNA polymerase betaHomo sapiens (human)
enzyme bindingDNA polymerase betaHomo sapiens (human)
metal ion bindingDNA polymerase betaHomo sapiens (human)
5'-deoxyribose-5-phosphate lyase activityDNA polymerase betaHomo sapiens (human)
class I DNA-(apurinic or apyrimidinic site) endonuclease activityDNA polymerase betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
nucleusDNA polymerase betaHomo sapiens (human)
nucleoplasmDNA polymerase betaHomo sapiens (human)
cytoplasmDNA polymerase betaHomo sapiens (human)
microtubuleDNA polymerase betaHomo sapiens (human)
spindle microtubuleDNA polymerase betaHomo sapiens (human)
protein-containing complexDNA polymerase betaHomo sapiens (human)
nucleusDNA polymerase betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (69)

Assay IDTitleYearJournalArticle
AID359795Polymerizing activity of exonuclase deficient HSV1 DNA polymerase UL42 D368A mutant assessed as rate of nucleotide incorporation by pre-steady state single turnover assay2007The Journal of biological chemistry, Aug-24, Volume: 282, Issue:34
Enzymatic therapeutic index of acyclovir. Viral versus human polymerase gamma specificity.
AID449346Inhibition of HIV1 reverse transcriptase-mediated viral DNA synthesis at 10 uM by PAGE2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
The nucleoside analogue D-carba T blocks HIV-1 reverse transcription.
AID239745Michaelis-Menten constant against HIV-1 wild-type strain reverse transcriptase2005Journal of medicinal chemistry, Jun-16, Volume: 48, Issue:12
Anti-HIV activity of (-)-(2R,4R)-1- (2-hydroxymethyl-1,3-dioxolan-4-yl)-thymine against drug-resistant HIV-1 mutants and studies of its molecular mechanism.
AID239754Michaelis-Menten constant against HIV-1 K65R/Q151M strain (DAPD/DXG) reverse transcriptase2005Journal of medicinal chemistry, Jun-16, Volume: 48, Issue:12
Anti-HIV activity of (-)-(2R,4R)-1- (2-hydroxymethyl-1,3-dioxolan-4-yl)-thymine against drug-resistant HIV-1 mutants and studies of its molecular mechanism.
AID563945Activity of wild-type HIV1 Reverse transcriptase2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID239763Michaelis-Menten constant against HIV-1 K65R strain (ddC/ddI/ABC/TFV/DXG) reverse transcriptase2005Journal of medicinal chemistry, Jun-16, Volume: 48, Issue:12
Anti-HIV activity of (-)-(2R,4R)-1- (2-hydroxymethyl-1,3-dioxolan-4-yl)-thymine against drug-resistant HIV-1 mutants and studies of its molecular mechanism.
AID564142Ratio of Kcat to Km for HIV1 Reverse transcriptase T165A/M184V mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID564138Ratio of Kcat to Km for HIV1 Reverse transcriptase T165A mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID529719Ratio of Kpol/Kd for DNA-dependent DNA polymerase activity of HIV 1 reverse transcriptase assessed as incorporation of dTMP by burst assay using DNA/DNA Primer/Template combination2008Antimicrobial agents and chemotherapy, Jun, Volume: 52, Issue:6
Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4'-ethynyl stavudine triphosphate.
AID239772Michaelis-Menten constant against HIV-1 D67N/K70R/T215Y/K219Q strain (AZT/ddI/d4T) reverse transcriptase2005Journal of medicinal chemistry, Jun-16, Volume: 48, Issue:12
Anti-HIV activity of (-)-(2R,4R)-1- (2-hydroxymethyl-1,3-dioxolan-4-yl)-thymine against drug-resistant HIV-1 mutants and studies of its molecular mechanism.
AID1053517Binding affinity to HIV1 reverse transcriptase assessed as compound incorporation into DNA by primer extension assay2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Clicking 3'-azidothymidine into novel potent inhibitors of human immunodeficiency virus.
AID563946Activity of HIV1 Reverse transcriptase P119S mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID282614Stability in CEM cell extract2004Journal of medicinal chemistry, Dec-30, Volume: 47, Issue:27
Synthesis of AZT 5'-triphosphate mimics and their inhibitory effects on HIV-1 reverse transcriptase.
AID529721Ratio of Kpol/Kd for RNA-dependent DNA polymerase activity of HIV 1 reverse transcriptase assessed as incorporation of dTMP by burst assay using RNA/DNA Primer/Template combination2008Antimicrobial agents and chemotherapy, Jun, Volume: 52, Issue:6
Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4'-ethynyl stavudine triphosphate.
AID572771Binding affinity to HIV1 reverse transcriptase2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Anti-human immunodeficiency virus activity, cross-resistance, cytotoxicity, and intracellular pharmacology of the 3'-azido-2',3'-dideoxypurine nucleosides.
AID563950Activity of HIV1 Reverse transcriptase P119S/M184V mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID239764Michaelis-Menten constant against HIV-1 L74V strain (ddC/ddI/ABC/TFV/DXG) reverse transcriptase2005Journal of medicinal chemistry, Jun-16, Volume: 48, Issue:12
Anti-HIV activity of (-)-(2R,4R)-1- (2-hydroxymethyl-1,3-dioxolan-4-yl)-thymine against drug-resistant HIV-1 mutants and studies of its molecular mechanism.
AID563952Activity of HIV1 Reverse transcriptase P119S/T165A/M184V mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID239748Michaelis-Menten constant against HIV-1 M184V strain (3TC) reverse transcriptase2005Journal of medicinal chemistry, Jun-16, Volume: 48, Issue:12
Anti-HIV activity of (-)-(2R,4R)-1- (2-hydroxymethyl-1,3-dioxolan-4-yl)-thymine against drug-resistant HIV-1 mutants and studies of its molecular mechanism.
AID563947Activity of HIV1 Reverse transcriptase T165A mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID239775Michaelis-Menten constant against HIV-1 A62V/V75I/F77L/F116Y/Q151M strain (multidrug resistant) reverse transcriptase2005Journal of medicinal chemistry, Jun-16, Volume: 48, Issue:12
Anti-HIV activity of (-)-(2R,4R)-1- (2-hydroxymethyl-1,3-dioxolan-4-yl)-thymine against drug-resistant HIV-1 mutants and studies of its molecular mechanism.
AID1865327Chemical stability in PBS buffer assessed half life measured after 24 hrs in presence of CEM/0 cell extract medium by RP-HPLC analysis relative to control2022Journal of medicinal chemistry, 09-22, Volume: 65, Issue:18
Triphosphate Prodrugs of the Anti-HIV-Active Compound 3'-Deoxy-3'-fluorothymidine (FLT).
AID564141Ratio of Kcat to Km for HIV1 Reverse transcriptase P119S/M184V mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID564143Ratio of Kcat to Km for HIV1 Reverse transcriptase P119S/T165A/M184V mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID432585Binding affinity to wild type HIV1 LAI reverse transcriptase2008Antimicrobial 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.
AID563951Activity of HIV1 Reverse transcriptase 165A/M184V mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID529694Inhibition of RNA-dependent DNA polymerase activity of HIV 1 reverse transcriptase M184V mutant assessed as incorporation of dTMP by burst assay using RNA/DNA Primer/Template combination2008Antimicrobial agents and chemotherapy, Jun, Volume: 52, Issue:6
Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4'-ethynyl stavudine triphosphate.
AID529697Inhibition of DNA-dependent DNA polymerase activity of HIV 1 reverse transcriptase assessed as incorporation of dTMP by burst assay using DNA/DNA Primer/Template combination2008Antimicrobial agents and chemotherapy, Jun, Volume: 52, Issue:6
Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4'-ethynyl stavudine triphosphate.
AID529706Activity of DNA-dependent DNA polymerase activity of HIV 1 reverse transcriptase M184V mutant assessed as incorporation of dTMP by burst assay using DNA/DNA Primer/Template combination2008Antimicrobial agents and chemotherapy, Jun, Volume: 52, Issue:6
Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4'-ethynyl stavudine triphosphate.
AID564140Ratio of Kcat to Km for HIV1 Reverse transcriptase P119S/T165A mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID432615Ratio of Kpol to Kd for wild type HIV1 LAI reverse transcriptase2008Antimicrobial 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.
AID529707Activity of DNA-dependent DNA polymerase activity of HIV 1 reverse transcriptase assessed as incorporation of dTMP by burst assay using DNA/DNA Primer/Template combination2008Antimicrobial agents and chemotherapy, Jun, Volume: 52, Issue:6
Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4'-ethynyl stavudine triphosphate.
AID563948Activity of HIV1 Reverse transcriptase M184V mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID432587Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant2008Antimicrobial 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.
AID1443140Inhibition of human DNA polymerase-gamma2017Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8
Discovery of a 2'-fluoro-2'-C-methyl C-nucleotide HCV polymerase inhibitor and a phosphoramidate prodrug with favorable properties.
AID432586Binding affinity to HIV1 LAI reverse transcriptase M184V mutant2008Antimicrobial 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.
AID432619Ratio of Kpol to Kd for HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V/G333D mutant2008Antimicrobial 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.
AID1443139Inhibition of human DNA polymerase-beta2017Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8
Discovery of a 2'-fluoro-2'-C-methyl C-nucleotide HCV polymerase inhibitor and a phosphoramidate prodrug with favorable properties.
AID529709Activity of RNA-dependent DNA polymerase activity of HIV 1 reverse transcriptase assessed as incorporation of dTMP by burst assay using RNA/DNA Primer/Template combination2008Antimicrobial agents and chemotherapy, Jun, Volume: 52, Issue:6
Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4'-ethynyl stavudine triphosphate.
AID572770Activity at HIV1 reverse transcriptase measured after 30 mins2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Anti-human immunodeficiency virus activity, cross-resistance, cytotoxicity, and intracellular pharmacology of the 3'-azido-2',3'-dideoxypurine nucleosides.
AID239774Michaelis-Menten constant against HIV-1 V75I/F77L/F116Y/Q151M strain (multidrug resistant) reverse transcriptase2005Journal of medicinal chemistry, Jun-16, Volume: 48, Issue:12
Anti-HIV activity of (-)-(2R,4R)-1- (2-hydroxymethyl-1,3-dioxolan-4-yl)-thymine against drug-resistant HIV-1 mutants and studies of its molecular mechanism.
AID529718Ratio of Kpol/Kd for DNA-dependent DNA polymerase activity of HIV 1 reverse transcriptase M184V mutant assessed as incorporation of dTMP by burst assay using DNA/DNA Primer/Template combination2008Antimicrobial agents and chemotherapy, Jun, Volume: 52, Issue:6
Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4'-ethynyl stavudine triphosphate.
AID1124556Inhibition of thymidine kinase in BHK21 (C13) cells using [14C]thymidine at 50 uM after 10 mins by liquid scintillation spectrometer analysis relative to control in presence of Mg2+1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Design of species- or isozyme-specific enzyme inhibitors. 1. Effect of thymidine substituents on affinity for the thymidine site of hamster cytoplasmic thymidine kinase.
AID1865328Chemical stability in PBS buffer assessed dephosphorylated half life measured after 24 hrs in presence of CEM/0 cell extract medium by RP-HPLC analysis relative to control2022Journal of medicinal chemistry, 09-22, Volume: 65, Issue:18
Triphosphate Prodrugs of the Anti-HIV-Active Compound 3'-Deoxy-3'-fluorothymidine (FLT).
AID432618Ratio of Kpol to Kd for HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V mutant2008Antimicrobial 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.
AID282613Stability in fetal calf serum at 500 uM at 37 degC2004Journal of medicinal chemistry, Dec-30, Volume: 47, Issue:27
Synthesis of AZT 5'-triphosphate mimics and their inhibitory effects on HIV-1 reverse transcriptase.
AID563953Ratio of Kcat to Km for wild-type HIV1 Reverse transcriptase2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID529708Activity of RNA-dependent DNA polymerase activity of HIV 1 reverse transcriptase M184V mutant assessed as incorporation of dTMP by burst assay using RNA/DNA Primer/Template combination2008Antimicrobial agents and chemotherapy, Jun, Volume: 52, Issue:6
Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4'-ethynyl stavudine triphosphate.
AID529720Ratio of Kpol/Kd for RNA-dependent DNA polymerase activity of HIV 1 reverse transcriptase M184V mutant assessed as incorporation of dTMP by burst assay using RNA/DNA Primer/Template combination2008Antimicrobial agents and chemotherapy, Jun, Volume: 52, Issue:6
Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4'-ethynyl stavudine triphosphate.
AID432588Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V mutant2008Antimicrobial 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.
AID239749Michaelis-Menten constant against HIV-1 T215Y strain (AZT) reverse transcriptase2005Journal of medicinal chemistry, Jun-16, Volume: 48, Issue:12
Anti-HIV activity of (-)-(2R,4R)-1- (2-hydroxymethyl-1,3-dioxolan-4-yl)-thymine against drug-resistant HIV-1 mutants and studies of its molecular mechanism.
AID563954Ratio of Kcat to Km for HIV1 Reverse transcriptase P119S mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID572772Ratio of Kpol to Kd for HIV1 reverse transcriptase2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Anti-human immunodeficiency virus activity, cross-resistance, cytotoxicity, and intracellular pharmacology of the 3'-azido-2',3'-dideoxypurine nucleosides.
AID359797Ratio of polymerization constant K to Kd for exonuclase deficient HSV1 DNA polymerase UL42 D368A mutant2007The Journal of biological chemistry, Aug-24, Volume: 282, Issue:34
Enzymatic therapeutic index of acyclovir. Viral versus human polymerase gamma specificity.
AID711538Ratio of Vmax to Km for HIV1 reverse transcriptase2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Synopsis of some recent tactical application of bioisosteres in drug design.
AID711522Activity of HIV1 reverse transcriptase assessed per unit of protein2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Synopsis of some recent tactical application of bioisosteres in drug design.
AID432589Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V/G333D mutant2008Antimicrobial 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.
AID432616Ratio of Kpol to Kd for HIV1 LAI reverse transcriptase M184V mutant2008Antimicrobial 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.
AID529695Inhibition of RNA-dependent DNA polymerase activity of HIV 1 reverse transcriptase assessed as incorporation of dTMP by burst assay using RNA/DNA Primer/Template combination2008Antimicrobial agents and chemotherapy, Jun, Volume: 52, Issue:6
Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4'-ethynyl stavudine triphosphate.
AID529696Inhibition of DNA-dependent DNA polymerase activity of HIV 1 reverse transcriptase M184V mutant assessed as incorporation of dTMP by burst assay using DNA/DNA Primer/Template combination2008Antimicrobial agents and chemotherapy, Jun, Volume: 52, Issue:6
Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4'-ethynyl stavudine triphosphate.
AID711539Activity of HIV1 reverse transcriptase2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Synopsis of some recent tactical application of bioisosteres in drug design.
AID563949Activity of HIV1 Reverse transcriptase P119S/T165A mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID432617Ratio of Kpol to Kd for HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant2008Antimicrobial 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.
AID238445Inhibitory constant against HIV-1 reverse transcriptase2005Journal of medicinal chemistry, Apr-07, Volume: 48, Issue:7
Synthesis of 2',3'-dideoxynucleoside 5'-alpha-P-borano-beta,gamma-(difluoromethylene)triphosphates and their inhibition of HIV-1 reverse transcriptase.
AID564139Ratio of Kcat to Km for HIV1 Reverse transcriptase M184V mutant2009Antimicrobial agents and chemotherapy, Nov, Volume: 53, Issue:11
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.
AID1811Experimentally measured binding affinity data derived from PDB2001Structure (London, England : 1993), Aug, Volume: 9, Issue:8
Structural basis for allosteric substrate specificity regulation in anaerobic ribonucleotide reductases.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2001Structure (London, England : 1993), Aug, Volume: 9, Issue:8
Structural basis for allosteric substrate specificity regulation in anaerobic ribonucleotide reductases.
AID1811Experimentally measured binding affinity data derived from PDB2005The FEBS journal, Jul, Volume: 272, Issue:14
Structural basis for the changed substrate specificity of Drosophila melanogaster deoxyribonucleoside kinase mutant N64D.
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB2005The FEBS journal, Jul, Volume: 272, Issue:14
Structural basis for the changed substrate specificity of Drosophila melanogaster deoxyribonucleoside kinase mutant N64D.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (732)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990229 (31.28)18.7374
1990's228 (31.15)18.2507
2000's172 (23.50)29.6817
2010's92 (12.57)24.3611
2020's11 (1.50)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 (%)
Trials4 (0.53%)5.53%
Reviews13 (1.73%)6.00%
Case Studies1 (0.13%)4.05%
Observational0 (0.00%)0.25%
Other733 (97.60%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (17)

ArticleYear
The kinetic effects on thymidine kinase 2 by enzyme-bound dTTP may explain the mitochondrial side effects of antiviral thymidine analogs.
Antimicrobial agents and chemotherapy, Volume: 55, Issue: 6
2011
Anti-human immunodeficiency virus activity, cross-resistance, cytotoxicity, and intracellular pharmacology of the 3'-azido-2',3'-dideoxypurine nucleosides.
Antimicrobial agents and chemotherapy, Volume: 53, Issue: 9
2009
Origin of pyrimidine deoxyribonucleotide pools in perfused rat heart: implications for 3'-azido-3'-deoxythymidine-dependent cardiotoxicity.
The Biochemical journal, Aug-27, Volume: 422, Issue: 3
2009
R964C mutation of DNA polymerase gamma imparts increased stavudine toxicity by decreasing nucleoside analog discrimination and impairing polymerase activity.
Antimicrobial agents and chemotherapy, Volume: 53, Issue: 6
2009
Selective radiosensitization of drug-resistant MutS homologue-2 (MSH2) mismatch repair-deficient cells by halogenated thymidine (dThd) analogues: Msh2 mediates dThd analogue DNA levels and the differential cytotoxicity and cell cycle effects of the dThd a
Cancer research, Oct-15, Volume: 60, Issue: 20
2000
Effect of ribavirin on zidovudine efficacy and toxicity in vitro: a concentration-dependent interaction.
AIDS research and human retroviruses, Dec-20, Volume: 14, Issue: 18
1998
Effect of adding the topoisomerase I poison 7-ethyl-10-hydroxycamptothecin (SN-38) to 5-fluorouracil and folinic acid in HCT-8 cells: elevated dTTP pools and enhanced cytotoxicity.
Cancer chemotherapy and pharmacology, Volume: 42, Issue: 5
1998
Modulation of fluorouracil cytotoxicity by interferon-alpha and -gamma.
Molecular pharmacology, Volume: 53, Issue: 2
1998
Nucleoside-mediated mitigation of 5-fluorouracil-induced toxicity in synchronized murine erythroleukemic cells.
Toxicology and applied pharmacology, Volume: 146, Issue: 1
1997
Enhanced cytotoxicity with interleukin-1 alpha and 5-fluorouracil in HCT116 colon cancer cells.
Oncology research, Volume: 6, Issue: 12
1994
Augmentation of 5-fluorouracil cytotoxicity in human colon cancer cells by dipyridamole.
Cancer research, Volume: 45, Issue: 7
1985
The effects of pyrimidine nucleotides on alkylating agent induced cytotoxicity and spontaneous and induced mutation to purine analog resistance in V79 cells.
Basic life sciences, Volume: 31
1985
Augmentation of methotrexate cytotoxicity in human colon cancer cells achieved through inhibition of thymidine salvage by dipyridamole.
Biochemical pharmacology, Mar-15, Volume: 36, Issue: 6
1987
Deoxyribonucleoside-induced selective modulation of cytotoxicity and mutagenesis.
Basic life sciences, Volume: 31
1985
2'-Deoxycytidine protects normal human bone marrow progenitor cells in vitro against the cytotoxicity of 3'-azido-3'-deoxythymidine with preservation of antiretroviral activity.
Blood, Nov-01, Volume: 74, Issue: 6
1989
Increased methotrexate-induced DNA strand breaks and cytotoxicity following mutational loss of thymidine kinase.
International journal of cancer, Apr-22, Volume: 48, Issue: 1
1991
Inhibition of 2-desamino-2-methyl-10-propagyl-5,8-dideazafolic acid cytotoxicity by 5,10-dideazatetrahydrofolate in L1210 cells with decrease in DNA fragmentation and deoxyadenosine triphosphate pools.
Biochemical pharmacology, Jul-15, Volume: 42, Issue: 3
1991
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (1)

ArticleYear
Phase II/pharmacodynamic trial of dose-intensive, weekly parenteral hydroxyurea and fluorouracil administered with interferon alfa-2a in patients with refractory malignancies of the gastrointestinal tract.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, Volume: 17, Issue: 6
1999
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (3)

ArticleYear
A DinB Ortholog Enables Mycobacterial Growth under dTTP-Limiting Conditions Induced by the Expression of a Mycobacteriophage-Derived Ribonucleotide Reductase Gene.
Journal of bacteriology, 01-15, Volume: 198, Issue: 2
2016
Bcl-2 oncogene protects a bone marrow-derived pre-B-cell line from 5'-fluor,2'-deoxyuridine-induced apoptosis.
Biochemical and biophysical research communications, Jul-15, Volume: 194, Issue: 1
1993
Zidovudine inhibits hepatitis B virus replication.
Antiviral research, Volume: 19, Issue: 2
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Interactions (1)

ArticleYear
Enhanced antitumor activity of 5-fluorouracil in combination with 2'-deoxyinosine in human colorectal cell lines and human colon tumor xenografts.
Clinical cancer research : an official journal of the American Association for Cancer Research, Volume: 6, Issue: 4
2000
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Natural Sources (1)

ArticleYear
Mycobacterium tuberculosis thymidylate synthase (ThyX) is a target for plumbagin, a natural product with antimycobacterial activity.
PloS one, Volume: 15, Issue: 2
2020
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]