Compounds > 3'-azido-2',3'-dideoxycytidine
Page last updated: 2024-12-08

3'-azido-2',3'-dideoxycytidine

Cross-References

ID SourceID
PubMed CID451374
CHEMBL ID1791029
SCHEMBL ID15643018
MeSH IDM0570444

Synonyms (21)

Synonym
84472-89-9
cs-91
azddcyd
3'-azido-2',3'-dideoxycytidine
4-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
3'-azido-ddc
cytidine, 3'-azido-2',3'-dideoxy-
3'-n3-ddc
4-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
CHEMBL1791029
nsc 382318
3'-azido-2'-deoxy-d-cytidine
cytidine,3'-azido-2',3'-dideoxy-
YIEFKLOVIROQIL-SHYZEUOFSA-N
DTXSID10233443
SCHEMBL15643018
2',3'-dideoxy-3'-azidocytidine
1-((2r,4s,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-imino-3,4-dihydropyrimidin-2(1h)-one
mfcd00880598
BS-42381
4-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

Assay IDTitleYearJournalArticle
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.
AID104310Effective dose achieving 50% protection of MT-4 cells against the cytopathic effect of HIV1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides.
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.
AID106768Cytotoxic dose required to reduce the viability of normal uninfected MT-4 cells by 50%1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides.
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.
AID154965Antiviral activity against HIV I strain (LAV) in human peripheral blood mononuclear (PBM) cells; Range is 0.66 - 1.191989Journal 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.
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.
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.
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.
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.
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.
AID235704Selectivity index of CD50 to ED50 of MT-4 cells1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides.
AID98521Ability to effect the replication of L1210 cells in vitro; IN-Inactive1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogues of pyrimidine deoxyribonucleoside.
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.
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).
[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's1 (12.50)18.2507
2000's0 (0.00)29.6817
2010's1 (12.50)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: 11.94

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 Index11.94 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.14 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.94)

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%
Other8 (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]		1.9610organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
cordycepin
[no description available]		1.97103'-deoxyribonucleoside;
adenosines		antimetabolite;
nucleoside antibiotic
deoxyuridine
[no description available]		1.9610pyrimidine 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		1.9710purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		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		2.6630dihydrofuran;
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.		2.0610adenosines;
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.		2.6830pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
alovudine
[no description available]		1.9710pyrimidine 2',3'-dideoxyribonucleoside
azides
Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.		2.0610pseudohalide 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.		3.3670azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
3'-azido-2',3'-dideoxyuridine
[no description available]		3.3570
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
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
3'-azido-2',3'-dideoxy-5-methylcytidine
3'-azido-2',3'-dideoxy-5-methylcytidine: inhibits reproduction of AIDS virus in cultured cells		3.0650
2',3'-dideoxythymidine
[no description available]		2.3720
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]		2.3620
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]		2.420
raluridine
raluridine: inhibitor of HIV; structure given in first source		1.9710
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
deoxyguanosine
[no description available]		1.9710purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
3'-azido-2',3'-dideoxyguanosine
[no description available]		2.0610
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]		02.3620
Sarcoma 180
An experimental sarcoma of mice.		01.9610
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		01.9610
chemdatabank.com