Compounds > 2',3'-dideoxyuridine
Page last updated: 2024-12-06

2',3'-dideoxyuridine

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

2',3'-dideoxyuridine, also known as ddUrd, is a nucleoside analog that acts as a chain terminator for DNA polymerase. It lacks the 3'-hydroxyl group that is essential for the formation of the phosphodiester bond between nucleotides during DNA replication. This absence prevents the addition of further nucleotides to the growing DNA strand. ddUrd is used in research to study DNA synthesis and replication processes. It is also an effective antiviral agent, particularly against HIV, as it inhibits the replication of the virus. The synthesis of ddUrd involves the modification of uridine, a naturally occurring nucleoside, through chemical reactions. ddUrd is a crucial tool in understanding the intricacies of DNA replication and its role in the development of antiviral therapies.'

Cross-References

ID SourceID
PubMed CID65161
CHEMBL ID1468
CHEBI ID183866
SCHEMBL ID8715
MeSH IDM0165529

Synonyms (28)

Synonym
BIDD:GT0651
5983-09-5
uridine, 2',3'-dideoxy-
ddurd
1-[(2r,5s)-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
2',3'-dideoxyuridine ,
2',3'-dideoxyuridine, 98%
CHEMBL1468
1-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
AKOS015907691
2',3'-dideoxy uridine
AM83954
SCHEMBL8715
BTOTXLJHDSNXMW-POYBYMJQSA-N
2',3'-dideoxy-uridine
dideoxyuridine
1-(2',3'-dideoxy-beta-ribofuranosyl)uracil
W-200600
AC-32185
DTXSID90208558
2,3-dideoxyuridine
1-((2r,5s)-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
CS-W015022
F12171
DS-14365
CHEBI:183866
HY-W014306
PD166046
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pyrimidine 2',3'-dideoxyribonucleoside
[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]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID423784Selectivity index, ratio of CC50 for human MT4 cells to EC50 for HIV1 3B2009Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9
Aryl nucleoside H-phosphonates. Part 16: synthesis and anti-HIV-1 activity of di-aryl nucleoside phosphotriesters.
AID423782Cytotoxicity against human MT4 cells after 96 hrs by MTT assay2009Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9
Aryl nucleoside H-phosphonates. Part 16: synthesis and anti-HIV-1 activity of di-aryl nucleoside phosphotriesters.
AID423783Antiviral activity against HIV1 3B infected in human MT4 cells assessed as protection from virus-induced cytopathogenicity after 4 days by MTT assay2009Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9
Aryl nucleoside H-phosphonates. Part 16: synthesis and anti-HIV-1 activity of di-aryl nucleoside phosphotriesters.
AID125177In vitro inhibitory activity against Moloney murine leukemia virus (M-MULV) replication, a mammalian T-lymphotropic retrovirus1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Synthesis and antiviral activity of various 3'-azido, 3'-amino, 2',3'-unsaturated, and 2',3'-dideoxy analogues of pyrimidine deoxyribonucleosides against retroviruses.
AID299251Inhibition of HIV1-induced cytopathogenicity in CEM/0 cells2007Bioorganic & medicinal chemistry letters, Jul-01, Volume: 17, Issue:13
Design, synthesis, and anti-HIV activity of 2',3'-didehydro-2',3'-dideoxyuridine (d4U), 2',3'-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives.
AID154959Antiviral activity against HIV I strain (LAV) in human peripheral blood mononuclear (PBM) cells1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral blood mononuclear cells.
AID299252Inhibition of HIV2-induced cytopathogenicity in CEM/0 cells2007Bioorganic & medicinal chemistry letters, Jul-01, Volume: 17, Issue:13
Design, synthesis, and anti-HIV activity of 2',3'-didehydro-2',3'-dideoxyuridine (d4U), 2',3'-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives.
AID299253Cytotoxicity against CEM/0 cells2007Bioorganic & medicinal chemistry letters, Jul-01, Volume: 17, Issue:13
Design, synthesis, and anti-HIV activity of 2',3'-didehydro-2',3'-dideoxyuridine (d4U), 2',3'-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives.
AID152643Cytotoxic effect in uninfected human peripheral blood mononuclear (PBM) cells; Not determined1989Journal of medicinal chemistry, Mar, Volume: 32, Issue:3
Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral blood mononuclear cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (25.00)18.7374
1990's3 (25.00)18.2507
2000's3 (25.00)29.6817
2010's3 (25.00)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: 11.80

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 Index11.80 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.43 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.80)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
thymidine
[no description available]		1.9810pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
uridine
[no description available]		1.9810uridinesdrug metabolite;
fundamental metabolite;
human metabolite
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).		2.0310thymidine 5'-monophosphatefundamental metabolite
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.		2.2110
deoxycytidine
[no description available]		7.0110pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae 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		2.6830dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
dideoxyadenosine
Dideoxyadenosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite.		7.420adenosines;
purine 2',3'-dideoxyribonucleoside		EC 3.5.4.4 (adenosine deaminase) inhibitor;
EC 4.6.1.1 (adenylate cyclase) inhibitor
zalcitabine
Zalcitabine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. 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 at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.. zalcitabine : A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.		2.3920pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
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.		2.9240azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
3'-azido-2',3'-dideoxyuridine
[no description available]		2.3720
2',3'-dideoxycytidinene
2',3'-dideoxycytidinene: 2',3'-unsaturated derivative of 2',3'-dideoxycytidine; potent inhibitor of HTLV-III in vitro; structure given in first source		1.9710
3'-azido-2',3'-dideoxy-5-bromouridine
3'-azido-2',3'-dideoxy-5-bromouridine: a potent, selective inhibitor of HIV replication; a weak competitive inhibitor of thymidylate kinase		2.3720
3'-azido-2',3'-dideoxy-5-methylcytidine
3'-azido-2',3'-dideoxy-5-methylcytidine: inhibits reproduction of AIDS virus in cultured cells		2.3720
phosphoramidic acid
phosphoramidic acid: urease inhibitor; RN given refers to parent cpd; structure; do not confuse with phosphoramidites, which are organophosphorus compounds		2.4920phosphoric acid derivative
2',3'-dideoxythymidine
[no description available]		2.3720
2',3'-didehydro-2',3'-dideoxyuridine
[no description available]		8.0950
5'-amino-2',5'-dideoxythymidine
5'-amino-5'-deoxythymidine: RN given refers to parent cpd		2.3720
2',3'-dideoxyuridine-5'-triphosphate
2',3'-dideoxyuridine-5'-triphosphate: inhibits HIV reverse transcriptase & has potent DNA chain termination activity		6.9710
3'-amino-2',3'-dideoxythymidine
[no description available]		2.3720
3'-amino-2',3'-dideoxyuridine
3'-amino-2',3'-dideoxyuridine: structure given in first source; a major metabolite of the antiviral agent, 3'-azido-2',3'-dideoxyuridine		1.9710
3'-fluoro-2',3'-dideoxyuridine
[no description available]		2.0510
organophosphonates
hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.		2.2110divalent inorganic anion;
phosphite ion
3'-azido-2',3'-dideoxycytidine
[no description available]		2.3720
5-bromo-2',3'-dideoxyuridine
5-bromo-2',3'-dideoxyuridine: structure given in first source		1.9710
pyrophosphate
Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.		2.1110diphosphate ion
didanosine
Didanosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.. didanosine : A purine 2',3'-dideoxyribonucleoside that is inosine in which the hydroxy groups at both the 2' and the 3' positions on the sugar moiety have been replaced by hydrogen. An antiviral drug, it is used as a medication to treat HIV/AIDS.		1.9710purine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor;
geroprotector;
HIV-1 reverse transcriptase inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
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.		02.6830