Compounds > 4'-azidothymidine
Page last updated: 2024-12-06

4'-azidothymidine

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Description

4'-Azidothymidine, commonly known as AZT, is a nucleoside analog reverse transcriptase inhibitor (NRTI) that is widely used in the treatment of HIV/AIDS. It was first synthesized in the 1960s as a potential anticancer agent. AZT blocks the activity of the HIV enzyme reverse transcriptase, which is essential for the virus to replicate. It does this by incorporating into the viral DNA chain and terminating further elongation. AZT is a highly effective antiretroviral drug and has been instrumental in prolonging the lives of people with HIV/AIDS. It is often used in combination with other antiretroviral drugs to create a potent cocktail that effectively suppresses viral replication. AZT is still widely studied to better understand its mechanism of action and to develop new and improved antiretroviral therapies.'

4'-azidothymidine: inhibits HIV replication in human lymphocytes [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72296
CHEMBL ID276563
SCHEMBL ID15532353
MeSH IDM0195699

Synonyms (14)

Synonym
1-(4-azido-2-deoxy-.beta.-d-erythro-pentofuranosyl)-5-methyl-2,4-dioxopyrimidine
130108-72-4
thymidine, 4'-azido-
1-[(2r,4s,5r)-5-azido-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione
4'-azidothymidine
CHEMBL276563
1-[(2r,4s,5r)-5-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
adrt
SCHEMBL15532353
DTXSID10156340
ZNPKSOLUIAAPQI-NYNCVSEMSA-N
A855677
4'-c-azidothymidine
AKOS040749965
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID125167In vitro Cytotoxic concentration in mock-infected A3.01 cells.1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID79107In vitro Cytotoxic concentration which destroyed HIV-1 LAV infected H9 cells completely1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID235699Selectivity index is defined as CC25(PBLcells) / CC50(PBL cells)1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104260In vitro Cytotoxic concentration which reduced G 910-6p2 (post-AZT) infected MT-2 cells by 50 percent1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID125169In vitro Cytotoxic concentration in mock-infected A3.01 cells - 100% toxicity.1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104259In vitro Cytotoxic concentration which reduced G 762-3(pre-AZT) infected MT-2 cells by 50 percent1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID7699Compound was tested in vitro for inhibition of cytopathogenicity of LAV(IIIB) in CD4+ T-cells (A3.01)1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID235695Selectivity index is defined as CC25(A3.01 cells) / CC50(A3.01 cells)1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104262In vitro Cytotoxic concentration which reduced HIV-1 LAV infected MT-2 cells by 50 percent1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID405582Cytotoxicity against human 293T cells assessed as inhibition of cell proliferation by tetrazolium dye method2007Antimicrobial agents and chemotherapy, Jul, Volume: 51, Issue:7
Selective inhibition of porcine endogenous retrovirus replication in human cells by acyclic nucleoside phosphonates.
AID104240In vitro Cytotoxic concentration which destroyed HIV-1 LAV infected MT-2 cells completely1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID405412Antiviral activity against PERV infected in human 293T cells assessed as inhibition of proximal DNA synthesis after 24 hrs by RT-PCR2007Antimicrobial agents and chemotherapy, Jul, Volume: 51, Issue:7
Selective inhibition of porcine endogenous retrovirus replication in human cells by acyclic nucleoside phosphonates.
AID79108In vitro Cytotoxic concentration which reduced HIV-1 LAV infected H9 cells by 25 percent1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID7700Compound was tested in vitro for inhibition of cytopathogenicity of LAV(IIIB) in CD4+ T-cells (A3.01); Not active1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104242In vitro Cytotoxic concentration which reduced HIV-1 LAV infected MT-2 cells by 25 percent1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID157418In vitro Cytotoxic concentration which reduced HIV-1 LAV infected peripheral blood lymphocytes by 50 percent1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104258In vitro Cytotoxic concentration which reduced G 691-2(post-AZT) infected MT-2 cells by 50 percent1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID157417In vitro Cytotoxic concentration which reduced HIV-1 LAV infected peripheral blood lymphocytes (PBL) by 25 percent1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID82574In vitro inhibitory activity against HIV was determined1994Journal of medicinal chemistry, Feb-18, Volume: 37, Issue:4
Solid-state and solution conformations of the potent HIV inhibitor, 4'-azidothymidine.
AID79129In vitro Cytotoxic concentration which reduced HIV-1 LAV infected H9 cells by 50 percent1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID235697Selectivity index is defined as CC25(H9 cells) / CC50(H9 cells)1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104241In vitro Cytotoxic concentration which destroyed HIV-1 LAV infected peripheral blood lymphocytes (PBL) completely1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID235698Selectivity index is defined as CC25(MT2 cells) / CC50(MT2 cells)1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104261In vitro Cytotoxic concentration which reduced H 112-2(pre-AZT) infected MT-2 cells by 50 percent1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
[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-19900 (0.00)18.7374
1990's4 (66.67)18.2507
2000's1 (16.67)29.6817
2010's0 (0.00)24.3611
2020's1 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.43

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 Index12.43 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.43)

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
nevirapine
Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.		2.0310cyclopropanes;
dipyridodiazepine		antiviral drug;
HIV-1 reverse transcriptase inhibitor
thymidine
[no description available]		6.9810pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
cytidine
[no description available]		7.2510cytidinesEscherichia 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		2.0310dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) 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.		3.2560azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
adefovir
adefovir: inhibitor of African swine fever virus. adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).. adefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.		2.03106-aminopurines;
ether;
phosphonic acids		antiviral drug;
DNA synthesis inhibitor;
drug metabolite;
HIV-1 reverse transcriptase inhibitor;
nephrotoxic agent
lamivudine
[no description available]		2.0310monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
stavudine triphosphate
stavudine triphosphate: shows termination substrate properties in DNA synthesis catalyzed by several different DNA polymerases; also abbreviated d4TTP		2.0310
zidovudine triphosphate
[no description available]		2.0310
5-methylcytidine
[no description available]		7.2510methylcytidine
4'-azidocytidine
4'-azidocytidine: antiviral; structure in first source		1.9810N-glycosyl compound
tenofovir
tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.		2.0310nucleoside analogue;
phosphonic acids		antiviral drug;
drug metabolite;
HIV-1 reverse transcriptase inhibitor
6-phosphonylmethoxyethoxy-2,4-diaminopyrimidine
[no description available]		2.0310
2',3'-didehydro-3'-deoxy-4'-ethynylthymidine
2',3'-didehydro-3'-deoxy-4'-ethynylthymidine: a highly active anti-HIV agent; structure in first source		2.0310
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.		07.6730