4'-azidothymidine

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

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 Source	ID
PubMed CID	72296
CHEMBL ID	276563
SCHEMBL ID	15532353
MeSH ID	M0195699

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 ID	Title	Year	Journal	Article
AID125167	In vitro Cytotoxic concentration in mock-infected A3.01 cells.	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID79107	In vitro Cytotoxic concentration which destroyed HIV-1 LAV infected H9 cells completely	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID235699	Selectivity index is defined as CC25(PBLcells) / CC50(PBL cells)	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104260	In vitro Cytotoxic concentration which reduced G 910-6p2 (post-AZT) infected MT-2 cells by 50 percent	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID125169	In vitro Cytotoxic concentration in mock-infected A3.01 cells - 100% toxicity.	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104259	In vitro Cytotoxic concentration which reduced G 762-3(pre-AZT) infected MT-2 cells by 50 percent	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID7699	Compound was tested in vitro for inhibition of cytopathogenicity of LAV(IIIB) in CD4+ T-cells (A3.01)	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID235695	Selectivity index is defined as CC25(A3.01 cells) / CC50(A3.01 cells)	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104262	In vitro Cytotoxic concentration which reduced HIV-1 LAV infected MT-2 cells by 50 percent	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID405582	Cytotoxicity against human 293T cells assessed as inhibition of cell proliferation by tetrazolium dye method	2007	Antimicrobial agents and chemotherapy, Jul, Volume: 51, Issue:7	Selective inhibition of porcine endogenous retrovirus replication in human cells by acyclic nucleoside phosphonates.
AID104240	In vitro Cytotoxic concentration which destroyed HIV-1 LAV infected MT-2 cells completely	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID405412	Antiviral activity against PERV infected in human 293T cells assessed as inhibition of proximal DNA synthesis after 24 hrs by RT-PCR	2007	Antimicrobial agents and chemotherapy, Jul, Volume: 51, Issue:7	Selective inhibition of porcine endogenous retrovirus replication in human cells by acyclic nucleoside phosphonates.
AID79108	In vitro Cytotoxic concentration which reduced HIV-1 LAV infected H9 cells by 25 percent	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID7700	Compound was tested in vitro for inhibition of cytopathogenicity of LAV(IIIB) in CD4+ T-cells (A3.01); Not active	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104242	In vitro Cytotoxic concentration which reduced HIV-1 LAV infected MT-2 cells by 25 percent	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID157418	In vitro Cytotoxic concentration which reduced HIV-1 LAV infected peripheral blood lymphocytes by 50 percent	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104258	In vitro Cytotoxic concentration which reduced G 691-2(post-AZT) infected MT-2 cells by 50 percent	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID157417	In vitro Cytotoxic concentration which reduced HIV-1 LAV infected peripheral blood lymphocytes (PBL) by 25 percent	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID82574	In vitro inhibitory activity against HIV was determined	1994	Journal of medicinal chemistry, Feb-18, Volume: 37, Issue:4	Solid-state and solution conformations of the potent HIV inhibitor, 4'-azidothymidine.
AID79129	In vitro Cytotoxic concentration which reduced HIV-1 LAV infected H9 cells by 50 percent	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID235697	Selectivity index is defined as CC25(H9 cells) / CC50(H9 cells)	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104241	In vitro Cytotoxic concentration which destroyed HIV-1 LAV infected peripheral blood lymphocytes (PBL) completely	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID235698	Selectivity index is defined as CC25(MT2 cells) / CC50(MT2 cells)	1992	Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8	Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides.
AID104261	In vitro Cytotoxic concentration which reduced H 112-2(pre-AZT) infected MT-2 cells by 50 percent	1992	Journal 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)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	4 (66.67)	18.2507
2000's	1 (16.67)	29.6817
2010's	0 (0.00)	24.3611
2020's	1 (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.

Metric	This Compound (vs All)
Research Demand Index	12.43 (24.57)
Research Supply Index	1.95 (2.92)
Research Growth Index	4.37 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.43)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	6 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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.	2.03	1	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor
thymidine [no description available]	6.98	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
cytidine [no description available]	7.25	1	cytidines	Escherichia 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	2.03	1	dihydrofuran; 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.	3.25	6	azide; 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.	2.03	1	6-aminopurines; ether; phosphonic acids	antiviral drug; DNA synthesis inhibitor; drug metabolite; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent
lamivudine [no description available]	2.03	1	monothioacetal; 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	2.03	1
zidovudine triphosphate [no description available]	2.03	1
5-methylcytidine [no description available]	7.25	1	methylcytidine
4'-azidocytidine 4'-azidocytidine: antiviral; structure in first source	1.98	1	N-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.	2.03	1	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
6-phosphonylmethoxyethoxy-2,4-diaminopyrimidine [no description available]	2.03	1
2',3'-didehydro-3'-deoxy-4'-ethynylthymidine 2',3'-didehydro-3'-deoxy-4'-ethynylthymidine: a highly active anti-HIV agent; structure in first source	2.03	1

Condition	Indicated	Relationship Strength	Studies	Trials
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.	0	7.67	3	0

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