Page last updated: 2024-11-06

2',3'-dideoxycytidinene

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

Description

2',3'-dideoxycytidinene is a synthetic nucleoside analog that has been shown to possess antiviral activity. It is a potent inhibitor of HIV-1 reverse transcriptase, and it has also been shown to inhibit the replication of other viruses, such as hepatitis B virus. The mechanism of action of 2',3'-dideoxycytidinene is believed to be through its incorporation into viral DNA, where it acts as a chain terminator. This compound has been studied extensively for its potential as an antiviral agent, and several clinical trials have been conducted. While it has shown promise in some studies, 2',3'-dideoxycytidinene has not yet been approved for use in humans. Further research is needed to optimize its efficacy and safety.'

2',3'-dideoxycytidinene: 2',3'-unsaturated derivative of 2',3'-dideoxycytidine; potent inhibitor of HTLV-III in vitro; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID64683
CHEMBL ID2115278
SCHEMBL ID5821
MeSH IDM0144463

Synonyms (24)

Synonym
2',3'-dideoxy-2',3'-didehydrocytidine
cytidine, 2,3'-didehydro-2',3'-dideoxy-
2',3'-didehydro-2',3'-dideoxycytidine
cytidine, 2',3'-didehydro-2',3'-dideoxy-
4-amino-1-(5-hydroxymethyl-2,5-dihydro-furan-2-yl)-1h-pyrimidin-2-one
ddecyd
4-amino-1-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one
7481-88-1
2',3'-dideoxycytidinene
2',3'-dideoxydidehydrocytidine
unii-ci9x00489l
ci9x00489l ,
CHEMBL2115278 ,
bdbm50421873
SCHEMBL5821
DTXSID30225784
2'3'-dideoxy-2',3'-didehydrocytidine
OOBICGOWICFMIX-POYBYMJQSA-N
4-amino-1-((2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)pyrimidin-2(1h)-one
Q27275480
dideoxycytidinene
CS-0433238
HY-145791
4-amino-1-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-1,2-dihydropyrimidin-2-one

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" The ability of ISIS 2922 to inhibit replication of HCMV when used in combination with other antiviral agents approved for treatment of HCMV disease was investigated using a 96-well immunoassay."( Antiviral activity of a phosphorothioate oligonucleotide complementary to human cytomegalovirus RNA when used in combination with antiviral nucleoside analogs.
Anderson, KP; Azad, RF; Brown-Driver, V; Buckheit, RW, 1995
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
pyrimidine nucleotide metabolic processDeoxycytidine kinaseHomo sapiens (human)
CMP biosynthetic processDeoxycytidine kinaseHomo sapiens (human)
dAMP salvageDeoxycytidine kinaseHomo sapiens (human)
nucleoside phosphate biosynthetic processDeoxycytidine kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
deoxyadenosine kinase activityDeoxycytidine kinaseHomo sapiens (human)
deoxycytidine kinase activityDeoxycytidine kinaseHomo sapiens (human)
deoxyguanosine kinase activityDeoxycytidine kinaseHomo sapiens (human)
ATP bindingDeoxycytidine kinaseHomo sapiens (human)
protein homodimerization activityDeoxycytidine kinaseHomo sapiens (human)
cytidine kinase activityDeoxycytidine kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleoplasmDeoxycytidine kinaseHomo sapiens (human)
cytosolDeoxycytidine kinaseHomo sapiens (human)
mitochondrionDeoxycytidine kinaseHomo sapiens (human)
cytoplasmDeoxycytidine kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID199981Inhibition of HIV-1 reverse transcriptase; + = active1994Journal of medicinal chemistry, Aug-05, Volume: 37, Issue:16
HIV-1 reverse transcriptase inhibitor design using artificial neural networks.
AID89157Effective concentration against HIV-1 in human peripheral blood mononuclear cells (PBMC)2004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.
AID56583Inhibitory affect against rabbit deoxycytidine kinase1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Synthesis and in vitro evaluation of some modified 4-thiopyrimidine nucleosides for prevention or reversal of AIDS-associated neurological disorders.
AID234204Therapeutic index (Ratio = ID50/ED50).1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID3034Concentration required to inhibit 50% of intracellular circular replication of HBV DNA using 2215 cell line1996Journal of medicinal chemistry, Apr-26, Volume: 39, Issue:9
Design and synthesis of 2',3'-dideoxy-2',3'-didehydro-beta-L-cytidine (beta-L-d4C) and 2',3'-dideoxy 2',3'-didehydro-beta-L-5-fluorocytidine (beta-L-Fd4C), two exceptionally potent inhibitors of human hepatitis B virus (HBV) and potent inhibitors of human
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.
AID155298Cytotoxicity against human peripheral blood mononuclear cells (PBMC)2004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.
AID24339t1/2 (half life) period was determined2004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV 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.
AID20871Partition coefficient (P) in 1-octanol and 0.1 M Na3PO4 at pH 71990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Synthesis and in vitro evaluation of some modified 4-thiopyrimidine nucleosides for prevention or reversal of AIDS-associated neurological disorders.
AID105756Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 5 uM concentration.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
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.
AID46361In vitro concentration required to decrease 50% of mitochondrial DNA content in CEM cells1996Journal of medicinal chemistry, Apr-26, Volume: 39, Issue:9
Design and synthesis of 2',3'-dideoxy-2',3'-didehydro-beta-L-cytidine (beta-L-d4C) and 2',3'-dideoxy 2',3'-didehydro-beta-L-5-fluorocytidine (beta-L-Fd4C), two exceptionally potent inhibitors of human hepatitis B virus (HBV) and potent inhibitors of human
AID46362In vitro concentration required to inhibit 50% of CEM cell growth1996Journal of medicinal chemistry, Apr-26, Volume: 39, Issue:9
Design and synthesis of 2',3'-dideoxy-2',3'-didehydro-beta-L-cytidine (beta-L-d4C) and 2',3'-dideoxy 2',3'-didehydro-beta-L-5-fluorocytidine (beta-L-Fd4C), two exceptionally potent inhibitors of human hepatitis B virus (HBV) and potent inhibitors of human
AID56585Inhibitory affect against rabbit deoxycytidine kinase and represented as molt/4F kinase.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Synthesis and in vitro evaluation of some modified 4-thiopyrimidine nucleosides for prevention or reversal of AIDS-associated neurological disorders.
AID105764Toxicity 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.
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.
AID105752Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 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.
AID3033Concentration required to inhibit 50% of extracellular circular replication of HBV DNA using 2215 cell line1996Journal of medicinal chemistry, Apr-26, Volume: 39, Issue:9
Design and synthesis of 2',3'-dideoxy-2',3'-didehydro-beta-L-cytidine (beta-L-d4C) and 2',3'-dideoxy 2',3'-didehydro-beta-L-5-fluorocytidine (beta-L-Fd4C), two exceptionally potent inhibitors of human hepatitis B virus (HBV) and potent inhibitors of human
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.
AID28713Partition coefficient (logP)1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
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.
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.
AID106908Concentration required to inhibit 50% of HIV activity in MT-2 cells1996Journal of medicinal chemistry, Apr-26, Volume: 39, Issue:9
Design and synthesis of 2',3'-dideoxy-2',3'-didehydro-beta-L-cytidine (beta-L-d4C) and 2',3'-dideoxy 2',3'-didehydro-beta-L-5-fluorocytidine (beta-L-Fd4C), two exceptionally potent inhibitors of human hepatitis B virus (HBV) and potent inhibitors of human
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.
AID105747Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.008 uM concentration.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 (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-199016 (55.17)18.7374
1990's10 (34.48)18.2507
2000's2 (6.90)29.6817
2010's1 (3.45)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: 10.68

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 Index10.68 (24.57)
Research Supply Index3.43 (2.92)
Research Growth Index4.11 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.68)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (3.45%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (3.45%)4.05%
Observational0 (0.00%)0.25%
Other27 (93.10%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]