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

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

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

Description

3'-azido-2',3'-dideoxy-5-methylcytidine, also known as AZT, is a nucleoside analog that inhibits the reverse transcriptase enzyme of HIV. It was the first drug approved for the treatment of HIV infection. AZT is synthesized by replacing the hydroxyl group at the 3' position of thymidine with an azido group. This structural modification prevents the incorporation of AZT into the growing DNA chain by reverse transcriptase, leading to the termination of viral DNA synthesis. AZT has been shown to be effective in reducing viral load and delaying the progression of HIV infection. However, it can cause significant side effects, including bone marrow suppression, anemia, and gastrointestinal problems. Despite the development of newer and more effective antiretroviral drugs, AZT remains an important part of HIV treatment regimens, especially in resource-limited settings. It is studied to understand its mechanisms of action, explore its potential in combination therapies, and identify strategies to minimize its adverse effects.'

3'-azido-2',3'-dideoxy-5-methylcytidine: inhibits reproduction of AIDS virus in cultured cells [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID64986
CHEMBL ID1791027
SCHEMBL ID15531809
MeSH IDM0161204

Synonyms (21)

Synonym
nsc687371
2(1h)-pyrimidinone, 4-amino-1-(3-azido-2,3-dideoxy-.beta.-d-erythro-pentofuranosyl)-5-methyl-
3'-n3-5-me-ddc
3'-azido-2',3'-dideoxy-5-methylcytidine
cytidine, 3'-azido-2',3'-dideoxy-5-methyl-
azddmec
az-5mec
87190-79-2
cs-92
4-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidin-2-one
4-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one
CHEMBL1791027
az-dcme
DTXSID40236164
SCHEMBL15531809
MS-23757
4-amino-1-((2r,4s,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidin-2(1h)-one
CS-0025552
HY-105268
A900569
AKOS040747903

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"74 h after intravenous and oral administration, respectively, and the oral bioavailability was about 21 percent."( Antiretroviral activity, biochemistry, and pharmacokinetics of 3'-azido-2',3'-dideoxy-5-methylcytidine.
Boudinot, FD; Chu, CK; Doshi, KJ; Eriksson, BF; McClure, HM; Oswald, B; Schinazi, RF; Sommadossi, JP, 1990)		0.52
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (19)

Assay IDTitleYearJournalArticle
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.
AID235875Ratio of CD50 to ED50 rvaluated for inhibition of HIV replication in MT-4 cells1988Journal of medicinal chemistry, Oct, Volume: 31, Issue:10
Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.
AID81438Dose required to inhibit cytopathic effect of human immunodeficiency virus replication in MT-4 cells.1988Journal of medicinal chemistry, Oct, Volume: 31, Issue:10
Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.
AID105758Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 5 uM concentration; Range is 40-601987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID201886In vitro inhibition against replication of Sarcoma-80 cells; inactive1983Journal of medicinal chemistry, Dec, Volume: 26, Issue:12
Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides.
AID210869Inhibitory activity against thymidine kinase (TK) from L1210 cells1983Journal of medicinal chemistry, Dec, Volume: 26, Issue:12
Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides.
AID56582Inhibitory activity against deoxycytidine kinase from L1210 cells1983Journal of medicinal chemistry, Dec, Volume: 26, Issue:12
Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides.
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.
AID105751Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 uM concentration; Range is 10-401987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
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.
AID154963Antiviral activity against HIV I strain (LAV) in human peripheral blood mononuclear (PBM) cells; Range is 0.081 - 0.221989Journal 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.
AID81069Cytotoxic dose required to reduce the viability of normal uninfected MT-4 cells.1988Journal of medicinal chemistry, Oct, Volume: 31, Issue:10
Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.
AID105753Protection 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.
AID98047In vitro inhibition against replication of L1210 murine cells; inactive1983Journal of medicinal chemistry, Dec, Volume: 26, Issue:12
Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides.
AID105765Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 125 uM concentration; Range is 10-401987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
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).
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (75.00)18.7374
1990's2 (25.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)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: 11.92

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 Index11.92 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.92)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (10.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
thymidine
[no description available]		1.9710pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
idoxuridine
[no description available]		1.9610organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
cordycepin
[no description available]		1.97103'-deoxyribonucleoside;
adenosines		antimetabolite;
nucleoside antibiotic
deoxycytidine
[no description available]		1.9710pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
deoxyuridine
[no description available]		2.3720pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
2'-deoxyadenosine
2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source		2.3720purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
uridine diphosphate glucuronic acid
Uridine Diphosphate Glucuronic Acid: A nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP iduronic acid, which donates iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones.. UDP-alpha-D-glucuronic acid : A UDP-sugar having alpha-D-glucuronic acid as the sugar component.		1.9810UDP-D-glucuronic acidEscherichia coli metabolite;
human metabolite;
mouse 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		2.6630dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
dideoxyadenosine
Dideoxyadenosine: 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 an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite.		1.9710adenosines;
purine 2',3'-dideoxyribonucleoside		EC 3.5.4.4 (adenosine deaminase) inhibitor;
EC 4.6.1.1 (adenylate cyclase) 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.		3.9840pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
alovudine
[no description available]		2.3720pyrimidine 2',3'-dideoxyribonucleoside
azides
Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.		3.4820pseudohalide anionmitochondrial respiratory-chain 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.		3.3570azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
3'-azido-2',3'-dideoxyuridine
[no description available]		3.0650
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		2.3720
2'3'-didehydro-2'3'-dideoxyadenosine
2'3'-didehydro-2'3'-dideoxyadenosine: structure given in first source		1.9710
3'-azido-2',3'-dideoxy-5-bromouridine
3'-azido-2',3'-dideoxy-5-bromouridine: a potent, selective inhibitor of HIV replication; a weak competitive inhibitor of thymidylate kinase		2.6630
2',3'-dideoxythymidine
[no description available]		2.6630
2',3'-didehydro-2',3'-dideoxyuridine
[no description available]		2.6630
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
adenosine 2',3'-ribo-epoxide
adenosine 2',3'-ribo-epoxide: structure		1.9710
3'-amino-2',3'-dideoxycytidine
[no description available]		1.9610
3'-amino-2',3'-dideoxythymidine
[no description available]		2.6630
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		2.6630
3'-fluoro-2',3'-dideoxyuridine
[no description available]		1.9710
3'-azido-2',3'-dideoxyadenosine
[no description available]		2.3720
3'-azido-2',3'-dideoxycytidine
[no description available]		3.0650
5-bromo-2',3'-dideoxyuridine
5-bromo-2',3'-dideoxyuridine: structure given in first source		1.9710
(2R,3S,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-3-oxolanol
[no description available]		1.97103'-deoxyribonucleoside;
purines
nadp
[no description available]		1.9810
3'-azido-2',3'-dideoxyuridine
3'-azido-2',3'-dideoxyuridine: structure given in first source		1.9810
deoxyguanosine
[no description available]		1.9710purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
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.		02.8840
Leukemia L 1210
[description not available]		01.9610
Sarcoma 180
An experimental sarcoma of mice.		01.9610