Page last updated: 2024-12-08

lamivudine triphosphate

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

Cross-References

ID SourceID
PubMed CID454110
CHEMBL ID1230
SCHEMBL ID12595501
MeSH IDM0375237

Synonyms (25)

Synonym
3tctp
(-)-sddctp
(-)3tc-5'tp
3tc-tp
[[(2r,5s)-5-(4-amino-2-oxo-pyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
l-sddctp
(-)-.beta.-l-2'-deoxy-3'-thiacytidine-5'-triphosphate
lamivudine triphosphate
bdbm50138406
[[[5-(4-amino-2-oxo-1h-pyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxyphosphonic acid
[(2r,5s)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)-1,3-oxathiolan-2-yl]methyl tetrahydrogen triphosphate
lamivudine 5'-triphosphate
CHEMBL1230 ,
3tc triphosphate
[[(2r,5s)-5-(4-amino-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
1rz ,
SCHEMBL12595501
143188-53-8
[[(2r,5s)-5-(4-azanyl-2-oxidanylidene-pyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy-oxidanyl-phosphoryl] phosphono hydrogen phosphate
Q27452393
unii-rm8y5kg43v
triphosphoric acid, p-(((2r,5s)-5-(4-amino-2-oxo-1(2h)-pyrimidinyl)-1,3-oxathiolan-2-yl)methyl) ester
rm8y5kg43v ,
DTXSID101343929
lamivudinetriphosphate

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In cell culture (-)3TC is less toxic than its d(+) isomer, (+)3TC, containing the natural nucleoside configuration, and both are considerably less toxic than ddC."( Insights into the molecular mechanism of mitochondrial toxicity by AIDS drugs.
Anderson, KS; Feng, JY; Johnson, AA; Johnson, KA, 2001
)
0.31
" In cell culture, (-)3TC is less toxic than its D (+) isomer, (+)3TC, containing the natural nucleoside configuration, and both are considerably less toxic than 2',3'-dideoxycytidine (ddC)."( Perspectives on the molecular mechanism of inhibition and toxicity of nucleoside analogs that target HIV-1 reverse transcriptase.
Anderson, KS, 2002
)
0.31

Pharmacokinetics

ExcerptReferenceRelevance
" A pharmacodynamic model that superimposes the pharmacokinetics of anti-HIV nucleoside reverse transcription (RT) and protease inhibitors over a previously published predator-prey model of HIV and CD4 dynamics was developed to address this need."( Development of a pharmacodynamic model for HIV treatment with nucleoside reverse transcriptase and protease inhibitors.
Hurwitz, SJ; Schinazi, RF, 2002
)
0.31
"To study the effect of mycophenolate mofetil therapy on the pharmacokinetic parameters of a number of antiretroviral drugs, on intracellular pools of deoxycytidine triphosphate (dCTP) and deoxyguanosine triphosphate (dGTP), and on intracellular concentrations of the triphosphate of lamivudine (3TCTP)."( Effect of mycophenolate mofetil on the pharmacokinetics of antiretroviral drugs and on intracellular nucleoside triphosphate pools.
Back, DJ; Beijnen, JH; Crommentuyn, KM; Hoggard, PG; Huitema, AD; Kewn, S; Lange, JM; Prins, JM; Sankatsing, SU; Sparidans, RW, 2004
)
0.32
"Randomised pharmacokinetic study."( Effect of mycophenolate mofetil on the pharmacokinetics of antiretroviral drugs and on intracellular nucleoside triphosphate pools.
Back, DJ; Beijnen, JH; Crommentuyn, KM; Hoggard, PG; Huitema, AD; Kewn, S; Lange, JM; Prins, JM; Sankatsing, SU; Sparidans, RW, 2004
)
0.32
" After 8 weeks of therapy, the plasma pharmacokinetic profiles of mycophenolic acid (the active metabolite of mycophenolate mofetil), abacavir, indinavir and nevirapine, and triphosphate concentrations (dCTP, dGTP and 3TCTP) in peripheral blood mononuclear cells, were determined."( Effect of mycophenolate mofetil on the pharmacokinetics of antiretroviral drugs and on intracellular nucleoside triphosphate pools.
Back, DJ; Beijnen, JH; Crommentuyn, KM; Hoggard, PG; Huitema, AD; Kewn, S; Lange, JM; Prins, JM; Sankatsing, SU; Sparidans, RW, 2004
)
0.32
" TFV-DP also had persistent intracellular levels on TDF discontinuation (median half-life of 150 hours, range: 60 to >175 hours)."( Intracellular pharmacokinetics of tenofovir diphosphate, carbovir triphosphate, and lamivudine triphosphate in patients receiving triple-nucleoside regimens.
Clark, N; Guyer, B; Hawkins, T; Kearney, BP; St Claire, RL; Veikley, W, 2005
)
0.55
"The population pharmacokinetic parameters of zidovudine (AZT), lamivudine (3TC), and their active intracellular metabolites in 75 naïve HIV-infected patients receiving an oral combination of AZT and 3TC twice daily as part of their multitherapy treatment in the COPHAR2-ANRS 111 trial are described."( Joint population pharmacokinetic analysis of zidovudine, lamivudine, and their active intracellular metabolites in HIV patients.
Bazzoli, C; Bénech, H; Duval, X; Mentré, F; Retout, S; Rey, E; Salmon, D; Tréluyer, JM, 2011
)
0.37
" Pharmacokinetic (PK) profiles (0 to 24 h) were assessed on days 10 and 30."( Pharmacokinetics of lamivudine and lamivudine-triphosphate after administration of 300 milligrams and 150 milligrams once daily to healthy volunteers: results of the ENCORE 2 study.
Amara, A; Back, DJ; Boffito, M; Else, LJ; Emery, S; Fahey, P; Hill, A; Jackson, A; Khoo, S; Lin, E; Puls, R; Siccardi, M; Tjia, J; Watson, V, 2012
)
0.38
" Here, we use population pharmacokinetic (PK) modeling-based methods to simultaneously describe parent and intracellular metabolite PK in blood, semen, and PBMCs and SMCs."( Pharmacokinetic Modeling of Lamivudine and Zidovudine Triphosphates Predicts Differential Pharmacokinetics in Seminal Mononuclear Cells and Peripheral Blood Mononuclear Cells.
Bridges, AS; Cohen, MS; Dumond, JB; Fiscus, SA; Forrest, A; Kashuba, AD; Kendrick, R; Reddy, YS; Troiani, L; Yang, KH, 2015
)
0.42

Compound-Compound Interactions

ExcerptReferenceRelevance
" These mt-QSARs offer also a good opportunity to construct drug-drug Complex Networks (CNs) that can be used to explore large and complex drug-viral species databases."( Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.
Chou, KC; González-Díaz, H; Martinez de la Vega, O; Prado-Prado, FJ; Ubeira, FM; Uriarte, E, 2009
)
0.35

Bioavailability

ExcerptReferenceRelevance
" We found particularly a gender effect on the apparent bioavailability of AZT, as well as on the mean plasma and intracellular concentrations of AZT, which were significantly higher in females than in males."( Joint population pharmacokinetic analysis of zidovudine, lamivudine, and their active intracellular metabolites in HIV patients.
Bazzoli, C; Bénech, H; Duval, X; Mentré, F; Retout, S; Rey, E; Salmon, D; Tréluyer, JM, 2011
)
0.37

Dosage Studied

ExcerptRelevanceReference
" Based on these findings this pharmacodynamic model can be applied to predict starting doses for a new agent based on simulated biological responses as a function of time for dosage regimens comprising one or two agents."( Development of a pharmacodynamic model for HIV treatment with nucleoside reverse transcriptase and protease inhibitors.
Hurwitz, SJ; Schinazi, RF, 2002
)
0.31
" Simulation with the model of plasma and intracellular concentrations for once- versus twice-daily regimens suggested that a daily dosing regimen with double doses could be appropriate."( Joint population pharmacokinetic analysis of zidovudine, lamivudine, and their active intracellular metabolites in HIV patients.
Bazzoli, C; Bénech, H; Duval, X; Mentré, F; Retout, S; Rey, E; Salmon, D; Tréluyer, JM, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1IC50 (µMol)5.00750.00011.076810.0000AID1387652; AID296101
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Ki0.18800.00031.552310.0000AID238445
[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)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Kd6.53750.00062.40599.8000AID432585; AID432586; AID432587; AID432588; AID572771; AID618865; AID618875; AID82971
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (39)

Assay IDTitleYearJournalArticle
AID296102Inhibition of HIV reverse transcriptase M184V mutant in PBM cells2007Bioorganic & medicinal chemistry letters, Jun-15, Volume: 17, Issue:12
Synthesis and evaluation of 2'-substituted cyclobutyl nucleosides and nucleotides as potential anti-HIV agents.
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.
AID82957Efficiency of incorporation into a DNA primer directed by a DNA template at the active site of HIV-1 reverse transcriptase2004Bioorganic & medicinal chemistry letters, Jan-19, Volume: 14, Issue:2
Effects of fluorine substitution of cytosine analogues on the binding affinity to HIV-1 reverse transcriptase.
AID323398Drug level in human CEM cells per 10^6 cells at 10 uM after 4 hrs2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Antiviral and cellular metabolism interactions between Dexelvucitabine and lamivudine.
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.
AID618875Binding affinity to HIV1 reverse transcriptase M184V mutant assessed as L-3'-azido-NTP incorporation in nascent DNA2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Synthesis, antiviral activity, cytotoxicity and cellular pharmacology of l-3'-azido-2',3'-dideoxypurine nucleosides.
AID618876Ratio Kpol to Kd for wild type HIV 1 reverse transcriptase2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Synthesis, antiviral activity, cytotoxicity and cellular pharmacology of l-3'-azido-2',3'-dideoxypurine nucleosides.
AID432620Binding affinity to HIV1 LAI reverse transcriptase M184V mutant relative to wild type2008Antimicrobial 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.
AID1387652Inhibition of full-length wild-type HIV1 reverse transcriptase expressed in Escherichia coli BL21(DE3) pre-incubated for 30 mins before addition of template/primer substrate and measured after 90 mins2018Journal of medicinal chemistry, 10-25, Volume: 61, Issue:20
Synthesis and Antiviral Evaluation of Carbocyclic Nucleoside Analogs of Nucleoside Reverse Transcriptase Translocation Inhibitor MK-8591 (4'-Ethynyl-2-fluoro-2'-deoxyadenosine).
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.
AID618877Ratio Kpol to Kd for wild type HIV 1 reverse transcriptase M184V mutant2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Synthesis, antiviral activity, cytotoxicity and cellular pharmacology of l-3'-azido-2',3'-dideoxypurine nucleosides.
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.
AID432623Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V/G333D mutant relative to wild type2008Antimicrobial 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.
AID392509Antiviral activity against Hepatitis B virus2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.
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.
AID432621Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant relative to wild type2008Antimicrobial 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.
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.
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.
AID83086Rate of incorporation into a DNA primer directed by a DNA template at the active site of HIV-1 reverse transcriptase2004Bioorganic & medicinal chemistry letters, Jan-19, Volume: 14, Issue:2
Effects of fluorine substitution of cytosine analogues on the binding affinity to HIV-1 reverse transcriptase.
AID296099Inhibition of recombinant wild type HIV reverse transcriptase2007Bioorganic & medicinal chemistry letters, Jun-15, Volume: 17, Issue:12
Synthesis and evaluation of 2'-substituted cyclobutyl nucleosides and nucleotides as potential anti-HIV agents.
AID422881Antiviral activity against HIV1 LAI with reverse transcriptase K70E mutation relative to wild type HIV1 LAI2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Novel drug resistance pattern associated with the mutations K70G and M184V in human immunodeficiency virus type 1 reverse transcriptase.
AID618879Selectivity ratio of Kpol to Kd for dCTP to Kpol to Kd for compound at HIV1 reverse transcriptase2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Synthesis, antiviral activity, cytotoxicity and cellular pharmacology of l-3'-azido-2',3'-dideoxypurine nucleosides.
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.
AID432622Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V mutant relative to wild type2008Antimicrobial 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.
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.
AID82971Equilibrium binding constant at the active site of HIV-1 reverse transcriptase2004Bioorganic & medicinal chemistry letters, Jan-19, Volume: 14, Issue:2
Effects of fluorine substitution of cytosine analogues on the binding affinity to HIV-1 reverse transcriptase.
AID404910Inhibition of HBV DNA polymerase2007Antimicrobial agents and chemotherapy, Jul, Volume: 51, Issue:7
Strong and selective inhibitors of hepatitis B virus replication among novel N4-hydroxy- and 5-methyl-beta-L-deoxycytidine analogues.
AID237107Half-life determined in fetal calf serum2005Journal 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.
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.
AID323399Drug level in human PBMC per 10^6 cells at 10 uM after 4 hrs2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Antiviral and cellular metabolism interactions between Dexelvucitabine and lamivudine.
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.
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.
AID296100Inhibition of wild type HIV reverse transcriptase in PBM cells2007Bioorganic & medicinal chemistry letters, Jun-15, Volume: 17, Issue:12
Synthesis and evaluation of 2'-substituted cyclobutyl nucleosides and nucleotides as potential anti-HIV agents.
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.
AID296101Inhibition of HIV reverse transcriptase M184I mutant in PBM cells2007Bioorganic & medicinal chemistry letters, Jun-15, Volume: 17, Issue:12
Synthesis and evaluation of 2'-substituted cyclobutyl nucleosides and nucleotides as potential anti-HIV agents.
AID618865Binding affinity to HIV1 reverse transcriptase assessed as L-3'-azido-NTP incorporation in nascent DNA2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Synthesis, antiviral activity, cytotoxicity and cellular pharmacology of l-3'-azido-2',3'-dideoxypurine nucleosides.
AID618934Selectivity ratio of Kpol to Kd for dCTP to Kpol to Kd for compound at HIV1 reverse transcriptase M184V mutant2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Synthesis, antiviral activity, cytotoxicity and cellular pharmacology of l-3'-azido-2',3'-dideoxypurine nucleosides.
AID572766Selectivity, ratio of Kpol to Kd for dCTP to Kpol to Kd for compound at 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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (43)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's34 (79.07)29.6817
2010's8 (18.60)24.3611
2020's1 (2.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.31

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

MetricThis Compound (vs All)
Research Demand Index11.31 (24.57)
Research Supply Index3.87 (2.92)
Research Growth Index5.18 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.31)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (9.30%)5.53%
Reviews1 (2.33%)6.00%
Case Studies1 (2.33%)4.05%
Observational0 (0.00%)0.25%
Other37 (86.05%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]