Compounds > 3'-amino-2',3'-dideoxyuridine
Page last updated: 2024-12-07

3'-amino-2',3'-dideoxyuridine

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Description

3'-amino-2',3'-dideoxyuridine (3'-NH2-ddU) is a nucleoside analog that has shown promising antiviral activity against a variety of viruses, including HIV, hepatitis B, and herpes simplex virus. Its synthesis typically involves the modification of uridine, where the 2' and 3' hydroxyl groups are replaced with hydrogen atoms, and an amino group is introduced at the 3' position. 3'-NH2-ddU acts as a chain terminator during DNA replication by inhibiting the activity of DNA polymerases. This inhibition occurs due to the lack of a 3' hydroxyl group, which is essential for the formation of phosphodiester bonds between nucleotides. 3'-NH2-ddU has been extensively studied for its potential therapeutic applications in treating viral infections. Its antiviral activity, mechanism of action, and potential side effects have been investigated in numerous preclinical and clinical studies.'

3'-amino-2',3'-dideoxyuridine: structure given in first source; a major metabolite of the antiviral agent, 3'-azido-2',3'-dideoxyuridine [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID122107
CHEMBL ID2021391
MeSH IDM0206368

Synonyms (12)

Synonym
3'-nh2-ddu
3'-amino-2',3'-dideoxyuridine
84472-86-6
uridine, 3'-amino-2',3'-dideoxy-
1-[(2r,4s,5s)-4-amino-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
amddu
1-[(2r,4s,5s)-4-amino-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
CHEMBL2021391
DTXSID50233442
mfcd00872044
A855651
1-[(2r,4s,5s)-4-amino-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" At an optimum dosage level of 40 mg/kg, 7 and 8 produced 90% and 60% "cures" (greater than 60-day survivors), respectively."( Antineoplastic activity of 3'-(chloroethyl)nitrosourea analogues of 2'-deoxyuridine and 2'-deoxy-5-fluorouridine.
Brubaker, WF; Lin, TS; Park, S; Prusoff, WH; Wang, ZH, 1986)		0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID155775Minimum inhibitory concentration against Pasteurella multocida1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID50534Minimum inhibitory concentration against Citrobacter freundii1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID98046In vitro inhibition against replication of L1210 murine 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.
AID163407Minimum inhibitory concentration against Proteus vulgaris1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID201396Minimum inhibitory concentration against Salmonella typhi1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID55275In vitro cytotoxicity against human D-38 cells.1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID162881Minimum inhibitory concentration against Proteus mirabilis1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
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.
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.
AID94565in vitro cytotoxicity against mouse L cells.1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID69202Minimum inhibitory concentration against Escherichia coli1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
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.
AID98520Ability to effect the replication of L1210 cells in vitro1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogues of pyrimidine deoxyribonucleoside.
AID97975Compound was tested in vitro for cytotoxicity against L1210 leukemia cells in tumor bearing mice.1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Antineoplastic activity of 3'-(chloroethyl)nitrosourea analogues of 2'-deoxyuridine and 2'-deoxy-5-fluorouridine.
AID200872Minimum inhibitory concentration against Salmonella Typhimurium1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID201885In vitro inhibition against replication of Sarcoma-80 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.
AID67853Minimum inhibitory concentration against Enterobacter aerogenes1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID199112Ability to effect the replication of S-180 cells in vitro1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogues of pyrimidine deoxyribonucleoside.
AID93874Minimum inhibitory concentration against Klebsiella pneumoniae1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID216569Minimum inhibitory concentration against Vibrio cholerae1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID154959Antiviral activity against HIV I strain (LAV) 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.
AID207203In vitro minimum inhibitory concentration against Staphylococcus aureus1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID31821In vitro antiviral activity against adeno virus using plaque reduction assay.1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID162934Minimum inhibitory concentration against Pseudomonas aeruginosa1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID203153Minimum inhibitory concentration against Serratia marcescens1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
AID203189Minimum inhibitory concentration against Shigella flexneri1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.
[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-19905 (83.33)18.7374
1990's1 (16.67)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: 12.35

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 Index12.35 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.29 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.35)

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
carmustine
Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.		1.9610N-nitrosoureas;
organochlorine compound		alkylating agent;
antineoplastic agent
idoxuridine
[no description available]		1.9610organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
deoxyuridine
[no description available]		2.3720pyrimidine 2'-deoxyribonucleosideEscherichia 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		1.9710dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) 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.		1.9810pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
azides
Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.		1.9810pseudohalide 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.		2.6630azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
3'-azido-2',3'-dideoxyuridine
[no description available]		2.6630
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		1.9710
3'-azido-2',3'-dideoxy-5-methylcytidine
3'-azido-2',3'-dideoxy-5-methylcytidine: inhibits reproduction of AIDS virus in cultured cells		2.6630
2',3'-dideoxythymidine
[no description available]		1.9710
2',3'-didehydro-2',3'-dideoxyuridine
[no description available]		1.9710
2',3'-dideoxyuridine
[no description available]		1.9710pyrimidine 2',3'-dideoxyribonucleoside
5'-amino-2',5'-dideoxythymidine
5'-amino-5'-deoxythymidine: RN given refers to parent cpd		1.9710
3'-amino-2',3'-dideoxycytidine
[no description available]		2.6530
3'-amino-2',3'-dideoxythymidine
[no description available]		2.8840
3'-azido-2',3'-dideoxycytidine
[no description available]		2.6630
nadp
[no description available]		1.9810
3'-azido-2',3'-dideoxyuridine
3'-azido-2',3'-dideoxyuridine: structure given in first source		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 1210
[description not available]		02.6530
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