Page last updated: 2024-12-06

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

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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]