Page last updated: 2024-12-07

2',3'-dideoxycytidine 5'-triphosphate

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

Description

2',3'-dideoxycytidine 5'-triphosphate (ddCTP) is a nucleoside analog that lacks the 2'-hydroxyl group and the 3'-hydroxyl group on the deoxyribose sugar. It is a potent inhibitor of DNA polymerase, particularly HIV-1 reverse transcriptase, and has been used as an antiviral drug to treat HIV infection. ddCTP is typically synthesized by enzymatic phosphorylation of 2',3'-dideoxycytidine using a kinase, such as adenosine kinase or thymidine kinase. Due to its lack of the 3'-hydroxyl group, ddCTP acts as a chain terminator during DNA synthesis, preventing further elongation of the DNA strand. This property makes ddCTP a valuable tool for studying DNA replication and for developing antiviral drugs. ddCTP is also used in the Sanger sequencing method for DNA sequencing, where it is incorporated into the DNA chain to terminate elongation.'

2',3'-dideoxycytidine 5'-triphosphate: inhibits vesicular stomatitis virus RNA synthesis [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID119119
CHEMBL ID1201384
SCHEMBL ID210922
MeSH IDM0113248
PubMed CID446696
CHEMBL ID1232305
SCHEMBL ID454264
MeSH IDM0113248

Synonyms (59)

Synonym
2',3'-dideoxycytidine triphosphate
triphosphoric acid, p-((5-(4-amino-2-oxo-1(2h)-pyrimidinyl)tetrahydro-2-furanyl)methyl) ester, (2s-cis)-
dideoxyctp
ddctp
zalcitabine triphosphate
2',3'-dideoxycytosine-5'-triphosphate
liposomal(ddctp)
cytidine 5'-(tetrahydrogen triphosphate), 2',3'-dideoxy-
ddc-tp
[[(2s,5r)-5-(4-amino-2-oxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
66004-77-1
2',3'-dideoxycytidine 5'-triphosphate
CHEMBL1201384
93939-77-6
[[(2s,5r)-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
2,3-dideoxycytidine 5-triphosphate
SCHEMBL210922
2'''',3''''-dideoxycytidine 5''''-triphosphate
bdbm50483420
2'',3''-dideoxycytidine 5''-triphosphate
dideoxycytidine triphosphate
dideoxycytidine 5'-triphosphate
ARLKCWCREKRROD-POYBYMJQSA-N
2',3'-dideoxy-cytidine-5'-triphosphate
((2s,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
Q27459169
CS-0141252
HY-137697
DTXSID701343965
AKOS040758264
5'-cytidine monophosphate
CHEMBL1232305 ,
brn 0556994
2',3'-dideoxycytidine monophosphate
5'-cytidylic acid, 2',3'-dideoxy-
2',3'-dideoxycytidine 5'-monophosphate
2',3'-dideoxycytidine-5'-monophosphate diammonium salt
[(2s,5r)-5-(4-amino-2-oxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
107133-41-5
ddcmp
2',3'-dideoxycytidine-5'-monophosphate
DB02883
[(2s,5r)-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate
104086-76-2
2',3'-dideoxy-5'-cytidylic acid
bdbm50349537
unii-x9m2w80kr9
x9m2w80kr9 ,
AKOS016009455
SCHEMBL454264
zalcitabine monophosphate sodium salt
((2s,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)tetrahydro-furan-2-yl)methyl dihydrogen phosphate
((2s,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate
dideoxycytidine 5'-monophosphate
[(2s,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
Q27093848
DTXSID30908787
5'-ytidine monophosphate
PD007555

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 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

Compound-Compound Interactions

ExcerptReferenceRelevance
" The effects of 3'-azido-3'-deoxythymidine (AZT), alone or in combination with ddCyd, on cell growth, DNA precursor pools, and accumulation of ddCTP were also studied."( 2',3'-Dideoxycytidine toxicity in cultured human CEM T lymphoblasts: effects of combination with 3'-azido-3'-deoxythymidine and thymidine.
Eriksson, S; Törnevik, Y, 1990
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pathways (1)

PathwayProteinsCompounds
Zalcitabine Action Pathway05

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
3-oxoacyl-[acyl-carrier-protein] synthase 3 Escherichia coliIC50 (µMol)2.10002.10004.20006.3000AID609868
[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 1Kd2.70000.00062.40599.8000AID572771
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (6)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
AID609869Toxicity in erythrocytes assessed as hemolytic activity2011Bioorganic & medicinal chemistry, Aug-01, Volume: 19, Issue:15
Design, synthesis and biological evaluation of urea derivatives from o-hydroxybenzylamines and phenylisocyanate as potential FabH inhibitors.
AID609868Inhibition of Escherichia coli FabH expressed in Escherichia coli DH10B cells assessed as incorporation of 3H signal in the product after 25 mins by liquid scintillation2011Bioorganic & medicinal chemistry, Aug-01, Volume: 19, Issue:15
Design, synthesis and biological evaluation of urea derivatives from o-hydroxybenzylamines and phenylisocyanate as potential FabH inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (41)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (4.88)18.7374
1990's29 (70.73)18.2507
2000's8 (19.51)29.6817
2010's2 (4.88)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.92

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 Index11.92 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index5.61 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.92)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (2.63%)5.53%
Trials0 (0.00%)5.53%
Reviews2 (5.26%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other35 (92.11%)84.16%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]