Page last updated: 2024-09-23

2',3'-dideoxy-2',3'-didehydro-2'-fluorocytidine

Description

2',3'-dideoxy-2',3'-didehydro-2'-fluorocytidine: has antiviral action against HIV-1; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72267
CHEMBL ID366193
SCHEMBL ID10410557
MeSH IDM0179029

Synonyms (12)

Synonym
1-(2,3-dideoxy-2-fluoro-.beta.-d-glycero-pent-2-eno-furanosyl)cytosine
2'-fd4c
d-2'-fd4cl .beta.-d-fd4c
122757-53-3
4-amino-1-[(2r,5s)-3-fluoro-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one
cytidine, 2',3'-didehydro-2',3'-dideoxy-2'-fluoro-
CHEMBL366193
2',3'-dideoxy-2',3'-didehydro-2'-fluorocytidine
2,3-ddfc
SCHEMBL10410557
DTXSID30924265
1-[3-fluoro-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-4-imino-1,4-dihydropyrimidin-2-ol

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1EC90 (µMol)4.90001.80004.90008.0000AID200011; AID200012
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID81089Anti-HIV activity was determined2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Structure-activity relationships of 2'-fluoro-2',3'-unsaturated D-nucleosides as anti-HIV-1 agents.
AID47305Cytotoxicity against CEM cells2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Structure-activity relationships of 2'-fluoro-2',3'-unsaturated D-nucleosides as anti-HIV-1 agents.
AID47624Cellular toxicity was measured in CEM cells after 8 days.50 tissue culture infectious doses were used.1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID217728Cytotoxicity against Vero cells was determined.2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Structure-activity relationships of 2'-fluoro-2',3'-unsaturated D-nucleosides as anti-HIV-1 agents.
AID47455Antiviral test was performed against HIV (LAV strain) on CEM cells using 50 tissue culture infectious units.1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID232768Selectivity index of IC50 and CD50 of the compound1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1).
AID246171In vitro effective concentration against HIV-1 in human peripheral blood mononuclear cells2005Journal of medicinal chemistry, Jun-02, Volume: 48, Issue:11
Synthesis, antiviral activity, and mechanism of drug resistance of D- and L-2',3'-didehydro-2',3'-dideoxy-2'-fluorocarbocyclic nucleosides.
AID44815Concentration of compound that inhibits incorporation of radiolabeled amino acids by 50 %1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1).
AID24340t1/2 (half life) period was determined; No decomposition observed up to 7 days2004Journal 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.
AID200011In vitro antiviral activity against HIV-1 Reverse transcriptase M184V mutant2003Bioorganic & medicinal chemistry letters, Jun-16, Volume: 13, Issue:12
The role of 2',3'-unsaturation on the antiviral activity of anti-HIV nucleosides against 3TC-resistant mutant (M184V).
AID154939Toxicity against human peripheral blood mononuclear (PBM) cells2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Structure-activity relationships of 2'-fluoro-2',3'-unsaturated D-nucleosides as anti-HIV-1 agents.
AID42390Antiviral activity against HIV-1 (RF strain) in C8166 cells1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1).
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.
AID200144Ratio for inhibition of HIV-1 RT to that of type and HIV-1 RT M184V mutant was determined2003Bioorganic & medicinal chemistry letters, Jun-16, Volume: 13, Issue:12
The role of 2',3'-unsaturation on the antiviral activity of anti-HIV nucleosides against 3TC-resistant mutant (M184V).
AID47621Antiviral test was performed against HIV (LAV strain) on CEM cells using 30 tissue culture infectious units. T1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID246159In vitro effective concentration against HBV in human peripheral blood mononuclear cells2005Journal of medicinal chemistry, Jun-02, Volume: 48, Issue:11
Synthesis, antiviral activity, and mechanism of drug resistance of D- and L-2',3'-didehydro-2',3'-dideoxy-2'-fluorocarbocyclic nucleosides.
AID200012In vitro antiviral activity against HIV-1 Reverse transcriptase wild type2003Bioorganic & medicinal chemistry letters, Jun-16, Volume: 13, Issue:12
The role of 2',3'-unsaturation on the antiviral activity of anti-HIV nucleosides against 3TC-resistant mutant (M184V).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (42.86)18.2507
2000's4 (57.14)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]

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]