Compounds > 2',3'-didehydro-2',3'-dideoxyuridine
Page last updated: 2024-09-23

2',3'-didehydro-2',3'-dideoxyuridine

Cross-References

ID SourceID
PubMed CID65159
CHEMBL ID89637
SCHEMBL ID543443
MeSH IDM0164122

Synonyms (21)

Synonym
CHEMBL89637 ,
ddeurd
d4u ,
1-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione
uridine, 2',3'-didehydro-2',3'-dideoxy-
5974-93-6
2',3'-dideoxyuridinene
1-((2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
bdbm50013115
1-(5-hydroxymethyl-2,5-dihydro-furan-2-yl)-1h-pyrimidine-2,4-dione (ddeurd)
2',3'-dideoxy-2',3'-didehydrouridine
2,4(1h,3h)-pyrimidinedione, 1-(2,5-dihydro-5-(hydroxymethyl)-2-furanyl)-, (2r-cis)-
2',3'-didehydro-2',3'-dideoxyuridine
SCHEMBL543443
NZXWQUCGACTHLK-POYBYMJQSA-N
AC-24683
CS-0100830
DTXSID50208453
AKOS025401704
F12170
HY-W048512

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine kinase, cytosolicHomo sapiens (human)Ki445.00000.09001.52137.0000AID210879
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
nucleobase-containing compound metabolic processThymidine kinase, cytosolicHomo sapiens (human)
deoxyribonucleoside monophosphate biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine metabolic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
protein homotetramerizationThymidine kinase, cytosolicHomo sapiens (human)
DNA synthesis involved in mitotic DNA replicationThymidine kinase, cytosolicHomo sapiens (human)
nucleobase-containing compound metabolic processDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
dUMP biosynthetic processDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
dTMP biosynthetic processDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
DNA replicationDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
dUTP catabolic processDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
thymidine kinase activityThymidine kinase, cytosolicHomo sapiens (human)
protein bindingThymidine kinase, cytosolicHomo sapiens (human)
ATP bindingThymidine kinase, cytosolicHomo sapiens (human)
zinc ion bindingThymidine kinase, cytosolicHomo sapiens (human)
identical protein bindingThymidine kinase, cytosolicHomo sapiens (human)
RNA bindingDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
dUTP diphosphatase activityDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
protein bindingDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
magnesium ion bindingDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
nucleusThymidine kinase, cytosolicHomo sapiens (human)
cytosolThymidine kinase, cytosolicHomo sapiens (human)
nucleusDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
nucleoplasmDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
mitochondrionDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
extracellular exosomeDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (31)

Assay IDTitleYearJournalArticle
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.
AID254408Inhibitory constant against Leishmania major deoxyuridine 5'-triphosphate nucleotidohydrolase2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Deoxyuridine triphosphate nucleotidohydrolase as a potential antiparasitic drug target.
AID255974In vitro cytotoxicity against rat skeletal myoblasts (L-6 cells) after 72 hours; nd=not determined2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Deoxyuridine triphosphate nucleotidohydrolase as a potential antiparasitic drug target.
AID255964In vitro inhibitory activity against Plasmodium falciparum as [3H]hypoxanthine (50 uL) incorporation at 37C2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Deoxyuridine triphosphate nucleotidohydrolase as a potential antiparasitic drug target.
AID106768Cytotoxic dose required to reduce the viability of normal uninfected MT-4 cells by 50%1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides.
AID105766Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 5 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID105750Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID254455Inhibitory constant against human deoxyuridine 5'-triphosphate nucleotidohydrolase expressed in Escherichia coli BL21 (DE3) cells2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Deoxyuridine triphosphate nucleotidohydrolase as a potential antiparasitic drug target.
AID154966Antiviral activity against HIV I strain (LAV) in human peripheral blood mononuclear (PBM) cells; Range is 68.3 - 79.91989Journal 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.
AID152642Cytotoxic effect in uninfected 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.
AID255969Inhibitory constant against Trypanosoma brucei rhodesiense upon incubation with the compound at 37 degrees C under a 5% CO2 atmosphere for 72 hours2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Deoxyuridine triphosphate nucleotidohydrolase as a potential antiparasitic drug target.
AID105756Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 5 uM concentration.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID255973In vitro growth inhibitory activity against Trypanosoma cruzi in rat L-6 cells upon incubation at 37 degrees C in 5% CO2 atmosphere for 4 days2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Deoxyuridine triphosphate nucleotidohydrolase as a potential antiparasitic drug target.
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.
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.
AID234204Therapeutic index (Ratio = ID50/ED50).1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID105764Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 125 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID515879Antimalarial activity against Plasmodium falciparum 3D7 at 100 uM by SYBR green assay2010Bioorganic & medicinal chemistry, Oct-15, Volume: 18, Issue:20
Potential application of thymidylate kinase in nucleoside analogue activation in Plasmodium falciparum.
AID254490Inhibitory constant against Plasmodium falciparum deoxyuridine 5'-triphosphate nucleotidohydrolase expressed in Escherichia coli BL21 (DE3) cells2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Deoxyuridine triphosphate nucleotidohydrolase as a potential antiparasitic drug target.
AID32065Protection of ATH8 cells against the cytopathic effect of HIV.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID20871Partition coefficient (P) in 1-octanol and 0.1 M Na3PO4 at pH 71990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Synthesis and in vitro evaluation of some modified 4-thiopyrimidine nucleosides for prevention or reversal of AIDS-associated neurological disorders.
AID255979In vitro growth inhibitory activity against Leishmania donovani amastigotes upon incubation with the compound at 37 degrees C under a 5% CO2 atmosphere for 96 hours; nd is not determined 2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Deoxyuridine triphosphate nucleotidohydrolase as a potential antiparasitic drug target.
AID105747Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.008 uM concentration.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
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.
AID105762Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID235704Selectivity index of CD50 to ED50 of MT-4 cells1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides.
AID254568Selectivity index for Plasmodium falciparum deoxyuridine 5'-triphosphate nucleotidohydrolase defined as (Ki Human)/(Ki Plasmodium falciparum)2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Deoxyuridine triphosphate nucleotidohydrolase as a potential antiparasitic drug target.
AID515880Antimalarial activity against Plasmodium falciparum 3D7 after 48 hrs by SYBR green assay2010Bioorganic & medicinal chemistry, Oct-15, Volume: 18, Issue:20
Potential application of thymidylate kinase in nucleoside analogue activation in Plasmodium falciparum.
AID32066Required dose to reduce viability of normal uninfected ATH8 cells.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID104310Effective dose achieving 50% protection of MT-4 cells against the cytopathic effect of HIV1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides.
AID210879Inhibitory affect against rabbit thymus thymidine kinase1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Synthesis and in vitro evaluation of some modified 4-thiopyrimidine nucleosides for prevention or reversal of AIDS-associated neurological disorders.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (37.50)18.7374
1990's2 (12.50)18.2507
2000's5 (31.25)29.6817
2010's3 (18.75)24.3611
2020's0 (0.00)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 (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
thymidine[no description available]medium20pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
deoxycytidine[no description available]medium20pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
stavudine[no description available]medium80dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
zalcitabine[no description available]medium70pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
zidovudine[no description available]medium80azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
2',3'-dideoxycytidinene[no description available]medium60
deoxy-4-thiothymidine[no description available]medium10
3'-azido-2',3'-dideoxyuridine[no description available]medium30
3'-azido-2',3'-dideoxycytidine[no description available]medium30
raluridine[no description available]medium10
3'-azido-2',3'-dideoxy-5-bromouridine[no description available]medium20
3'-azido-2',3'-dideoxy-5-methylcytidine[no description available]medium30
2',3'-dideoxythymidine[no description available]medium30
2',3'-dideoxyuridine[no description available]medium50pyrimidine 2',3'-dideoxyribonucleoside
5'-amino-2',5'-dideoxythymidine[no description available]medium20
3'-amino-2',3'-dideoxythymidine[no description available]medium20
3'-amino-2',3'-dideoxyuridine[no description available]medium10
2'-deoxyadenosine[no description available]medium10purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
dideoxyadenosine[no description available]medium20adenosines;
purine 2',3'-dideoxyribonucleoside		EC 3.5.4.4 (adenosine deaminase) inhibitor;
EC 4.6.1.1 (adenylate cyclase) inhibitor
alovudine[no description available]medium10pyrimidine 2',3'-dideoxyribonucleoside
2'3'-didehydro-2'3'-dideoxyadenosine[no description available]medium10
3'-azido-2',3'-dideoxyadenosine[no description available]medium10
5-bromo-2',3'-dideoxyuridine[no description available]medium10
3'-fluoro-2',3'-dideoxyuridine[no description available]medium20
3'-azido-2',3'-dideoxyguanosine[no description available]medium10
pyrophosphate[no description available]medium10diphosphate ion
phosphoramidic acid[no description available]medium20phosphoric acid derivative
triazoles[no description available]medium101,2,3-triazole
uridine[no description available]medium10uridinesdrug metabolite;
fundamental metabolite;
human metabolite
trovirdine[no description available]medium10
thymidine monophosphate[no description available]medium10thymidine 5'-monophosphatefundamental metabolite
didanosine[no description available]medium10purine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor;
geroprotector;
HIV-1 reverse transcriptase inhibitor
cytarabine[no description available]medium10beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
3'-azido-2',3'-dideoxyuridine[no description available]medium10
ConditionIndicatedRelationship StrengthStudiesTrials
Acquired Immune Deficiency Syndrome0low10
Acquired Immuno-Deficiency Syndrome0low10
Acquired Immunodeficiency Syndrome0low10
Acquired-Immune Deficiency Syndrome Dementia Complex0low10
AIDS0low10
AIDS Dementia Complex0low10
AIDS Encephalopathy0low10
AIDS-Related Dementia Complex0low10
Dementia Complex, Acquired Immune Deficiency Syndrome0low10
Dementia Complex, AIDS-Related0low10
Encephalopathy, AIDS0low10
Encephalopathy, HIV0low10
HIV0low60
HIV Dementia0low10
HIV Encephalopathy0low10
HIV-1 Cognitive and Motor Complex0low10
HIV-1-Associated Cognitive Motor Complex0low10
HIV-Associated Cognitive Motor Complex0low10
Immunodeficiency Syndrome, Acquired0low10
Immunologic Deficiency Syndrome, Acquired0low10

Research Highlights

Safety/Toxicity (1)

ArticleYear
Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides.
Journal of medicinal chemistry, Volume: 33, Issue: 6		1990
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]