Compounds > 3'-azido-2',3'-dideoxy-5-bromouridine
Page last updated: 2024-12-06

3'-azido-2',3'-dideoxy-5-bromouridine

Description

3'-azido-2',3'-dideoxy-5-bromouridine (also known as AZBDU) is a nucleoside analog that has been investigated for its potential antiviral and anticancer properties. It is a derivative of uridine, with a bromine atom at the 5' position and an azido group at the 3' position. AZBDU is a chain terminator for DNA polymerase, which makes it a potential therapeutic agent for treating viral infections like HIV. Its antiviral activity is attributed to its ability to inhibit viral DNA synthesis by acting as a substrate for the reverse transcriptase enzyme used by HIV to replicate. AZBDU has shown promising results in preclinical studies against HIV and other viruses. However, further research is needed to determine its safety and efficacy in humans.'

3'-azido-2',3'-dideoxy-5-bromouridine: a potent, selective inhibitor of HIV replication; a weak competitive inhibitor of thymidylate kinase [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID64978
CHEMBL ID1791024
MeSH IDM0212336

Synonyms (14)

Synonym
105784-82-5
uridine, 3'-azido-5-bromo-2',3'-dideoxy-
3'-n3-5-br-ddu
5-br-azu
azbdurd
5brazdu
azddbru
3'-azido-2',3'-dideoxy-5-bromouridine
1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-bromo-pyrimidine-2,4-dione
1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-bromopyrimidine-2,4-dione
CHEMBL1791024
3'-azido-5-bromo-2',3'-dideoxyuridine
DTXSID40147342
VKYMRXNXDPKKRV-RRKCRQDMSA-N
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID230271Ratio of TICD50 to that of IC50 of human immunodeficiency virus (HIV-1)1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia
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.
AID163315Concentration of compound required to inhibit 50% of viral replication of Rauscher-Murine leukemia virus1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia
AID640485Cytotoxicity against human HuH7 cells by [3H]thymidine incorporation assay2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Antimycobacterial activities of 5-alkyl (or halo)-3'-substituted pyrimidine nucleoside analogs.
AID84646Activity against HTLV-III/LAV/AAV, was determined in vitro.1987Journal 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.
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.
AID640481Antimycobacterial activity against Mycobacterium avium ATCC 25291 assessed as growth inhibition at 0.5 to 100 ug/ml by microplate alamar blue assay2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Antimycobacterial activities of 5-alkyl (or halo)-3'-substituted pyrimidine nucleoside analogs.
AID640484Cytotoxicity against human HuH7 cells up to 100 ug/ml by [3H]thymidine incorporation assay2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Antimycobacterial activities of 5-alkyl (or halo)-3'-substituted pyrimidine nucleoside analogs.
AID230269Ratio of TICD50 to that of IC50 of Rauscher-Murine leukemia virus (R-MuLv)1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia
AID640482Cytotoxicity against human HuH7 cells up to 100 ug/ml by XTT assay2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Antimycobacterial activities of 5-alkyl (or halo)-3'-substituted pyrimidine nucleoside analogs.
AID81411Inhibition of HIV-1 replication in human peripheral blood mononuclear cells.1988Journal of medicinal chemistry, Feb, Volume: 31, Issue:2
Synthesis and antiviral activity of various 3'-azido analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1, HTLV-III/LAV).
AID45016Concentration of compound required to inhibit 50% of viral replication of human immunodeficiency virus in CEM-F cells1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia
AID45017Concentration of compound required to inhibit 50% of host cell replication of human immunodeficiency virus in CEM-F cells1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia
AID640335Antimycobacterial activity against Mycobacterium tuberculosis H37Ra assessed as growth inhibition at 100 ug/ml by microplate alamar blue assay2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Antimycobacterial activities of 5-alkyl (or halo)-3'-substituted pyrimidine nucleoside analogs.
AID640329Antimycobacterial activity against Mycobacterium bovis BCG assessed as growth inhibition at 100 ug/ml by microplate alamar blue assay2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Antimycobacterial activities of 5-alkyl (or halo)-3'-substituted pyrimidine nucleoside analogs.
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.
AID640483Cytotoxicity against human HuH7 cells by XTT assay2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Antimycobacterial activities of 5-alkyl (or halo)-3'-substituted pyrimidine nucleoside analogs.
AID163316Concentration of compound required to inhibit 50% of host cell replication of Rauscher-Murine leukemia virus1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (66.67)18.7374
1990's1 (16.67)18.2507
2000's0 (0.00)29.6817
2010's1 (16.67)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: 12.21

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 Index12.21 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.16 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.21)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
idoxuridine
[no description available]		1.9810organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
cycloserine
Cycloserine: Antibiotic substance produced by Streptomyces garyphalus.. D-cycloserine : A 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine--D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis).		2.07104-amino-1,2-oxazolidin-3-one;
organonitrogen heterocyclic antibiotic;
organooxygen heterocyclic antibiotic;
zwitterion		antiinfective agent;
antimetabolite;
antitubercular agent;
metabolite;
NMDA receptor agonist
deoxyuridine
[no description available]		1.9810pyrimidine 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		2.3720dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) 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.		1.9710pyrimidine 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.		2.8840azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
3'-azido-2',3'-dideoxyuridine
[no description available]		2.8840
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-methylcytidine
3'-azido-2',3'-dideoxy-5-methylcytidine: inhibits reproduction of AIDS virus in cultured cells		2.6630
2',3'-dideoxythymidine
[no description available]		2.6630
2',3'-didehydro-2',3'-dideoxyuridine
[no description available]		2.3720
2',3'-dideoxyuridine
[no description available]		2.3720pyrimidine 2',3'-dideoxyribonucleoside
5'-amino-2',5'-dideoxythymidine
5'-amino-5'-deoxythymidine: RN given refers to parent cpd		2.3720
clarithromycin
Clarithromycin: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.. clarithromycin : The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.		2.0710macrolide antibioticantibacterial drug;
environmental contaminant;
protein synthesis inhibitor;
xenobiotic
3'-amino-2',3'-dideoxythymidine
[no description available]		2.6830
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'-azido-2',3'-dideoxycytidine
[no description available]		2.6630
5-bromo-2',3'-dideoxyuridine
5-bromo-2',3'-dideoxyuridine: structure given in first source		1.9710
rifampin
Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)		2.0710cyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion		angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis 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.		02.3720
chemdatabank.com