Compounds > 3'-amino-2',3'-dideoxycytidine
Page last updated: 2024-12-06

3'-amino-2',3'-dideoxycytidine

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3'-amino-2',3'-dideoxycytidine, also known as 3'-amino-ddC, is a nucleoside analog that has been studied as a potential antiviral agent. It is a structural analog of cytidine, a naturally occurring nucleoside, and differs from cytidine by the absence of a hydroxyl group at the 2' and 3' positions of the deoxyribose sugar and the presence of an amino group at the 3' position. 3'-amino-ddC has been shown to inhibit the replication of human immunodeficiency virus (HIV), the virus that causes acquired immunodeficiency syndrome (AIDS), by acting as a chain terminator during reverse transcription. The mechanism of action involves the incorporation of 3'-amino-ddC into the growing DNA chain of the viral genome, leading to premature termination of DNA synthesis and subsequent inhibition of viral replication. 3'-amino-ddC has also been investigated for its potential therapeutic effects in other viral infections, such as hepatitis B and hepatitis C. However, further research is needed to evaluate its clinical efficacy and safety.'

Cross-References

ID SourceID
PubMed CID73515
CHEMBL ID1791179
SCHEMBL ID4117883
MeSH IDM0117413

Synonyms (14)

Synonym
cytidine, 3'-amino-2',3'-dideoxy-
nsc 365107
84472-90-2
4-amino-1-[(2r,4s,5s)-4-amino-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
3'-amino-2',3'-dideoxycytidine
4-amino-1-((2r,4s,5s)-4-amino-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1h)-one
A840798
CHEMBL1791179
AKOS015896790
LDQAHTVPOZCQNH-SHYZEUOFSA-N
SCHEMBL4117883
mfcd00870894
3-amino-2,3-dideoxycytidine
4-amino-1-[(2r,4s,5s)-4-amino-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 (26)

Assay IDTitleYearJournalArticle
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.
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.
AID120894Ratio of treated to that of control was determined in mice tested in vivo(on day 31)1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogues of pyrimidine deoxyribonucleoside.
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.
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.
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.
AID98883Compound was tested for the inhibition of the transport of aminoisobutyric acid into L1210 cells at the 10 uM concentration after <20 min1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Synthesis and biological activity of several amino nucleoside-platinum(II) complexes.
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.
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.
AID98885Compound was tested for the inhibition of the transport of methionine into L1210 cells at the 10 uM concentration after <20 min1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Synthesis and biological activity of several amino nucleoside-platinum(II) complexes.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (66.67)18.7374
1990's3 (33.33)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: 12.05

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 Index12.05 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.05)

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%
Other9 (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
cytarabine
[no description available]		2.3720beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
deoxycytidine
[no description available]		2.3720pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
deoxyuridine
[no description available]		1.9610pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
durapatite
Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).		1.9810
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.		3.0750pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase 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.		1.9610azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
3'-azido-2',3'-dideoxyuridine
[no description available]		2.3620
3'-azido-2',3'-dideoxy-5-methylcytidine
3'-azido-2',3'-dideoxy-5-methylcytidine: inhibits reproduction of AIDS virus in cultured cells		1.9610
3'-amino-2',3'-dideoxythymidine
[no description available]		2.6530
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		2.6530
3'-azido-2',3'-dideoxycytidine
[no description available]		2.3620
aphidicolin
Aphidicolin: An antiviral antibiotic produced by Cephalosporium aphidicola and other fungi. It inhibits the growth of eukaryotic cells and certain animal viruses by selectively inhibiting the cellular replication of DNA polymerase II or the viral-induced DNA polymerases. The drug may be useful for controlling excessive cell proliferation in patients with cancer, psoriasis or other dermatitis with little or no adverse effect upon non-multiplying cells.. aphidicolin : A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.		1.9810tetracyclic diterpenoidantimicrobial agent;
antimitotic;
antineoplastic agent;
antiviral drug;
apoptosis inducer;
Aspergillus metabolite;
DNA synthesis inhibitor;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
fungal metabolite
alpha-chymotrypsin
Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 1210
[description not available]		03.2260
Sarcoma 180
An experimental sarcoma of mice.		02.3720
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		01.9610
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		01.9810
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		01.9810
Carcinoma, Ehrlich Tumor
A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.		01.9710