Compounds > 3'-azido-2',3'-dideoxyuridine
Page last updated: 2024-09-23

3'-azido-2',3'-dideoxyuridine

Description

3'-azido-2',3'-dideoxyuridine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID55262
CHEMBL ID591804
SCHEMBL ID15531699
MeSH IDM0163839
PubMed CID3908006
MeSH IDM0163839

Synonyms (37)

Synonym
uridine, 3'-azido-2',3'-dideoxy- and jps-783
nsc-380882
azdu
azddu & gm-csf
uridine, 3'-azido-2',3'-dideoxy-
1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
azddu
3'-azido-2',3'-dideoxyuridine & granulocyte-macrophage colony-stimulating factor
cs-87
inchi=1/c9h11n5o4/c10-13-12-5-3-8(18-6(5)4-15)14-2-1-7(16)11-9(14)17/h1-2,5-6,8,15h,3-4h2,(h,11,16,17)/t5-,6+,8+/m0/s1
zsnnbspefviuds-shyzeuofsa-
CHEMBL591804
navuridine
1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
azurd
unii-ps28w65479
navuridine [inn]
ps28w65479 ,
navuridine [mart.]
3'-azido-2',3'dideoxyuridine
ZSNNBSPEFVIUDS-SHYZEUOFSA-N
SCHEMBL15531699
1-(3-azido-2,3-dideoxypentofuranosyl)-4-hydroxypyrimidin-2(1h)-one
DTXSID901004737
mfcd00870324
1-((2r*,4s*,5s*)-4-azido-5-hydroxymethyl-tetrahydro-furan-2-yl)-1h-pyrimidine-2,4-dione
cs87
Q27286725
MS-23568
A855471
1-((2r,4s,5s)-4-azido-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
AKOS040744855
uridine,3'-dideoxy-
84472-85-5
3'-azido-2',3'-dideoxyuridine
1-[4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
HMS3371J13

Bioassays (34)

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.
AID24310Time taken to decrease plasma concentration to half of its initial concentration after iv administration1996Journal of medicinal chemistry, Apr-26, Volume: 39, Issue:9
Nucleoside conjugates. 15. Synthesis and biological activity of anti-HIV nucleoside conjugates of ether and thioether phospholipids.
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.
AID98522Ability 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.
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.
AID14573Pharmacokinetic parameter AUC in mice following a single dose intravenous administration of the compound1996Journal of medicinal chemistry, Apr-26, Volume: 39, Issue:9
Nucleoside conjugates. 15. Synthesis and biological activity of anti-HIV nucleoside conjugates of ether and thioether phospholipids.
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.
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.
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.
AID13511AUC in brain1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Brain targeting of anti-HIV nucleosides: synthesis and in vitro and in vivo studies of dihydropyridine derivatives of 3'-azido-2',3'-dideoxyuridine and 3'-azido-3'-deoxythymidine.
AID452270Cytotoxicity against human PBMC after 5 days2010Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1
Synthesis and evaluation of 3'-azido-2',3'-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus.
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
AID13512AUC in serum1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Brain targeting of anti-HIV nucleosides: synthesis and in vitro and in vivo studies of dihydropyridine derivatives of 3'-azido-2',3'-dideoxyuridine and 3'-azido-3'-deoxythymidine.
AID25126Half life of the compound1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Brain targeting of anti-HIV nucleosides: synthesis and in vitro and in vivo studies of dihydropyridine derivatives of 3'-azido-2',3'-dideoxyuridine and 3'-azido-3'-deoxythymidine.
AID23323Relative brain exposure of the compound1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Brain targeting of anti-HIV nucleosides: synthesis and in vitro and in vivo studies of dihydropyridine derivatives of 3'-azido-2',3'-dideoxyuridine and 3'-azido-3'-deoxythymidine.
AID452269Antiviral activity against HIV1 LAI infected in human PBM cells after 5 days2010Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1
Synthesis and evaluation of 3'-azido-2',3'-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus.
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.
AID154964Antiviral activity against HIV I strain (LAV) in human peripheral blood mononuclear (PBM) cells; Range is 0.18 - 0.461989Journal 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.
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.
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.
AID125176Antiviral activity against Moloney murine leukemia virus1989Journal 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.
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.
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
AID152616In vitro anti-HIV activity was determined in peripheral blood mononuclear cells.1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Brain targeting of anti-HIV nucleosides: synthesis and in vitro and in vivo studies of dihydropyridine derivatives of 3'-azido-2',3'-dideoxyuridine and 3'-azido-3'-deoxythymidine.
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.
AID152633Antiviral activity against HIV-1 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.
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
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
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).
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
AID452272Cytotoxicity against african green monkey Vero cells after 5 days2010Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1
Synthesis and evaluation of 3'-azido-2',3'-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus.
AID452271Cytotoxicity against human CEM cells after 5 days2010Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1
Synthesis and evaluation of 3'-azido-2',3'-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-199010 (38.46)18.7374
1990's12 (46.15)18.2507
2000's3 (11.54)29.6817
2010's1 (3.85)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews1 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other11 (100.00%)84.16%
Other16 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
stavudine[no description available]medium30dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
zalcitabine[no description available]medium20pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
zidovudine[no description available]medium100azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
2',3'-dideoxycytidinene[no description available]medium20
2',3'-didehydro-2',3'-dideoxyuridine[no description available]medium30
3'-azido-2',3'-dideoxycytidine[no description available]medium70
raluridine[no description available]medium10
3'-azido-2',3'-dideoxy-5-bromouridine[no description available]medium40
2',3'-dideoxythymidine[no description available]medium30
3'-azido-2',3'-dideoxy-5-methylcytidine[no description available]medium50
2',3'-dideoxyuridine[no description available]medium20pyrimidine 2',3'-dideoxyribonucleoside
5'-amino-2',5'-dideoxythymidine[no description available]medium20
3'-amino-2',3'-dideoxythymidine[no description available]medium30
3'-amino-2',3'-dideoxyuridine[no description available]medium30
cordycepin[no description available]medium103'-deoxyribonucleoside;
adenosines		antimetabolite;
nucleoside antibiotic
2'-deoxyadenosine[no description available]medium10purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
alovudine[no description available]medium10pyrimidine 2',3'-dideoxyribonucleoside
adenosine 2',3'-ribo-epoxide[no description available]medium10
3'-fluoro-2',3'-dideoxyuridine[no description available]medium10
3'-azido-2',3'-dideoxyadenosine[no description available]medium20
(2R,3S,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-3-oxolanol[no description available]medium103'-deoxyribonucleoside;
purines
deoxyguanosine[no description available]medium10purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
5-bromo-2',3'-dideoxyuridine[no description available]medium10
idoxuridine[no description available]medium10organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
deoxyuridine[no description available]medium10pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
3'-amino-2',3'-dideoxycytidine[no description available]medium20
3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside[no description available]medium10
3'-azido-2',3'-dideoxyguanosine[no description available]medium10
zidovudine[no description available]medium170azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
valine[no description available]medium10L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid;
valine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
thymine[no description available]medium10pyrimidine nucleobase;
pyrimidone		Escherichia coli metabolite;
human metabolite;
mouse metabolite
1-((2-hydroxyethoxy)methyl)-6-(phenylthio)thymine[no description available]medium10aryl sulfide;
primary alcohol;
pyrimidone		antiviral drug;
HIV-1 reverse transcriptase inhibitor
3'-azido-2',3'-dideoxy-5-methylcytidine[no description available]medium10
3'-amino-2',3'-dideoxyuridine[no description available]medium10
uridine diphosphate glucuronic acid[no description available]medium10UDP-D-glucuronic acidEscherichia coli metabolite;
human metabolite;
mouse metabolite
nadp[no description available]medium10
azides[no description available]medium10pseudohalide anionmitochondrial respiratory-chain inhibitor
thymidine[no description available]medium10pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
dipyridamole[no description available]medium10piperidines;
pyrimidopyrimidine;
tertiary amino compound;
tetrol		adenosine phosphodiesterase inhibitor;
EC 3.5.4.4 (adenosine deaminase) inhibitor;
platelet aggregation inhibitor;
vasodilator agent
adenine[no description available]medium106-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
didanosine[no description available]medium10purine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor;
geroprotector;
HIV-1 reverse transcriptase inhibitor
stavudine[no description available]medium20dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
adefovir[no description available]medium106-aminopurines;
ether;
phosphonic acids		antiviral drug;
DNA synthesis inhibitor;
drug metabolite;
HIV-1 reverse transcriptase inhibitor;
nephrotoxic agent
organophosphonates[no description available]medium10divalent inorganic anion;
phosphite ion
chloramphenicol[no description available]medium10C-nitro compound;
carboxamide;
diol;
organochlorine compound		antibacterial drug;
antimicrobial agent;
Escherichia coli metabolite;
geroprotector;
Mycoplasma genitalium metabolite;
protein synthesis inhibitor
morphine[no description available]medium10morphinane alkaloid;
organic heteropentacyclic compound;
tertiary amino compound		anaesthetic;
drug allergen;
environmental contaminant;
geroprotector;
mu-opioid receptor agonist;
opioid analgesic;
plant metabolite;
vasodilator agent;
xenobiotic
dihydropyridines[no description available]medium20
3'-azido-3'-deoxythymidine 5'phosphate[no description available]medium10
5'-(1,4-dihydro-1-methyl-3-pyridinylcarbonyl)-3'-azido-3'-deoxythymidine[no description available]medium10
2',3'-dideoxythymidine[no description available]medium10
2',3'-didehydro-2',3'-dideoxyuridine[no description available]medium10
ConditionIndicatedRelationship StrengthStudiesTrials
Body Weight0low10
HIV0low50
Leukemia L 12100low30
Leukemia L12100low30
Sarcoma 1800low10
Sarcoma 180, Crocker0low10
Acquired Immune Deficiency Syndrome0low10
Acquired Immuno-Deficiency Syndrome0low10
Acquired Immunodeficiency Syndrome0low10
AIDS0low10
HIV0low60
Immunodeficiency Syndrome, Acquired0low10
Immunologic Deficiency Syndrome, Acquired0low10
Pregnancy0low10
Sensitivity and Specificity0low10

Research Highlights

Safety/Toxicity (1)

ArticleYear
Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides.
Journal of medicinal chemistry, Volume: 33, Issue: 6		1990
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (3)

ArticleYear
Pharmacokinetic evaluation of 3'-azido-2', 3'-dideoxyuridine-5'-O-valinate-hydrochloride as a prodrug of the anti-HIV nucleoside 3'-azido-2', 3'-dideoxyuridine.
Antiviral chemistry & chemotherapy, Volume: 14, Issue: 5		2003
Hybrid pharmacokinetic models to describe anti-HIV nucleoside brain disposition following parent and prodrug administration in mice.
Pharmaceutical research, Volume: 8, Issue: 2		1991
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (2)

ArticleYear
Pharmacokinetic evaluation of 3'-azido-2', 3'-dideoxyuridine-5'-O-valinate-hydrochloride as a prodrug of the anti-HIV nucleoside 3'-azido-2', 3'-dideoxyuridine.
Antiviral chemistry & chemotherapy, Volume: 14, Issue: 5		2003
Lymphatic distribution of 3'-azido-3'-deoxythymidine and 3'-azido-2',3'-dideoxyuridine in mice.
Drug metabolism and disposition: the biological fate of chemicals, Volume: 23, Issue: 6		1995
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (1)

ArticleYear
Lymphatic distribution of 3'-azido-3'-deoxythymidine and 3'-azido-2',3'-dideoxyuridine in mice.
Drug metabolism and disposition: the biological fate of chemicals, Volume: 23, Issue: 6		1995
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]