Compounds > 2',3'-dideoxy-beta-5-fluorocytidine
Page last updated: 2024-12-06

2',3'-dideoxy-beta-5-fluorocytidine

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Description

This nucleoside analog is a potent inhibitor of HIV-1 reverse transcriptase. It is a chain terminator, meaning it stops the process of DNA synthesis by incorporating itself into the growing DNA chain. This lack of a 3' hydroxyl group prevents the addition of further nucleotides. The compound has been studied extensively for its antiviral properties and potential as a treatment for HIV infection. It is known to be effective in suppressing viral replication and has been used in combination therapy regimens. The compound is also under investigation for its potential to inhibit other viruses.'

2',3'-dideoxy-beta-5-fluorocytidine: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72413
CHEMBL ID40724
SCHEMBL ID913431
MeSH IDM0227430

Synonyms (16)

Synonym
4-amino-5-fluoro-1-[(2s,5r)-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
.beta.-l-2',3'-dideoxy-5-fluorocytidine
.beta.-l-fddc
l-fddc
.beta.-l-5-fddc
147058-39-7
5-f-b.-l-ddc
2(1h)-pyrimidinone, 4-amino-5-fluoro-1-[(2s,5r)-tetrahydro-5-(hydroxymethyl)-2-furanyl]-
CHEMBL40724
(2s-cis)-4-amino-5-fluoro-1-(tetrahydro-5-(hydroxymethyl)-2-furanyl)-2(1h)-pyrimidinone
2',3'-dideoxy-beta-l-5-fluorocytidine
2(1h)-pyrimidinone, 4-amino-5-fluoro-1-(tetrahydro-5-(hydroxymethyl)-2-furanyl)-, (2s-cis)-
2',3'-dideoxy-beta-5-fluorocytidine
beta-fddc
SCHEMBL913431
DTXSID80163586

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Pharmacokinetic parameters were obtained on the basis of a two-compartment open model with a first-order elimination from the central compartment."( Pharmacokinetics of beta-L-2',3'-dideoxy-5-fluorocytidine in rhesus monkeys.
Cretton-Scott, E; Gosselin, G; Imbach, JL; Martin, LT; Mathe, C; McClure, HM; Schinazi, RF; Sommadossi, JP; Zhou, XJ, 1999)		0.3

Bioavailability

ExcerptReferenceRelevance
" The absolute bioavailability of orally administered beta-L-FddC ranged from 56 to 66%."( Pharmacokinetics of beta-L-2',3'-dideoxy-5-fluorocytidine in rhesus monkeys.
Cretton-Scott, E; Gosselin, G; Imbach, JL; Martin, LT; Mathe, C; McClure, HM; Schinazi, RF; Sommadossi, JP; Zhou, XJ, 1999)		0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID88982Compound concentration required to inhibit the viral cell proliferation by 50% against HIV; Range = 0.3-0.51998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Synthesis and biological evaluation of a series of 2'-fluorinated-2',3'-dideoxy-2',3'-didehydro-(L)-nucleosides.
AID88976The compound was tested for antiviral activity against Hepatitis B virus in human hepatoma cells.1994Journal of medicinal chemistry, Mar-18, Volume: 37, Issue:6
Synthesis and biological evaluation of 2',3'-dideoxy-L-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus (HBV).
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
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
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
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
AID32240Compound was evaluated for cytotoxicity by HIV cytopathic effect assay performed with ATH8 cells at a concentration of 50(uM)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Potential anti-AIDS drugs. 2',3'-Dideoxycytidine analogues.
AID32366Percent protection of ATH8 cells from HIV-induced cytopathic effects at a concentration of 1 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID233710Compound was evaluated for the protective effect against HTLV-III/LAV (HIV) pathogenesis at a concentration of 0.5(uM)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Potential anti-AIDS drugs. 2',3'-Dideoxycytidine analogues.
AID233724Compound was evaluated for the protective effect against HTLV-III/LAV (HIV) pathogenesis at a concentration of 5(uM)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Potential anti-AIDS drugs. 2',3'-Dideoxycytidine analogues.
AID235196Therapeutic index (IC50/EC50) was determined1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID32364Percent protection of ATH8 cells from HIV-induced cytopathic effects at a concentration of 0.2 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
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
AID233708Compound was evaluated for the protective effect against HTLV-III/LAV (HIV) pathogenesis at a concentration of 0.05(uM)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Potential anti-AIDS drugs. 2',3'-Dideoxycytidine analogues.
AID104417Compound was tested for anti-HIV activity in MT-2/ IIIB cells and the ratio of the drug concentration (ID50) required to inhibit cell growth was reported.1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Synthesis and biological evaluation of a series of 2'-fluorinated-2',3'-dideoxy-2',3'-didehydro-(L)-nucleosides.
AID32365Percent protection of ATH8 cells from HIV-induced cytopathic effects at a concentration of 0.5 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID47456Compound concentration required to inhibit cell growth by 50% against CEM cells1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Synthesis and biological evaluation of a series of 2'-fluorinated-2',3'-dideoxy-2',3'-didehydro-(L)-nucleosides.
AID28713Partition coefficient (logP)1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID32244Percent cytotoxicity against ATH8 cells at a concentration of 1 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID233726Compound was evaluated for the protective effect against HTLV-III/LAV (HIV) pathogenesis at a concentration of 50(uM)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Potential anti-AIDS drugs. 2',3'-Dideoxycytidine analogues.
AID43709In vitro cytotoxicity against human CCRF-CEM T-lymphoblastic leukemia cells was determined1994Journal of medicinal chemistry, Mar-18, Volume: 37, Issue:6
Synthesis and biological evaluation of 2',3'-dideoxy-L-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus (HBV).
AID106912The compound was tested for antiviral activity against HIV-1 in MT-2 cells1994Journal of medicinal chemistry, Mar-18, Volume: 37, Issue:6
Synthesis and biological evaluation of 2',3'-dideoxy-L-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus (HBV).
AID32224Compound was evaluated for cytotoxicity by HIV cytopathic effect assay performed with ATH8 cells at a concentration of 0.5(uM)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Potential anti-AIDS drugs. 2',3'-Dideoxycytidine analogues.
AID32243Percent cytotoxicity against ATH8 cells at a concentration of 0.5 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID32222Compound was evaluated for cytotoxicity by HIV cytopathic effect assay performed with ATH8 cells at a concentration of 0.05(uM)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Potential anti-AIDS drugs. 2',3'-Dideoxycytidine analogues.
AID32245Percent cytotoxicity against ATH8 cells at a concentration of 5 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID47138Effect on HIV-induced cytopathogenesis in CEM cells.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID32238Compound was evaluated for cytotoxicity by HIV cytopathic effect assay performed with ATH8 cells at a concentration of 5(uM)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Potential anti-AIDS drugs. 2',3'-Dideoxycytidine analogues.
AID86850Compound concentration required to inhibit the viral cell proliferation by 50% against HBV1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Synthesis and biological evaluation of a series of 2'-fluorinated-2',3'-dideoxy-2',3'-didehydro-(L)-nucleosides.
AID43694Concentration of compound required to inhibit the synthesis of mitochondrial DNA (mt DNA) in human CCRF-CEM T-lymphoblastic leukemia cells1994Journal of medicinal chemistry, Mar-18, Volume: 37, Issue:6
Synthesis and biological evaluation of 2',3'-dideoxy-L-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus (HBV).
AID32242Percent cytotoxicity against ATH8 cells at a concentration of 0.2 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID47425Effect on HIV-induced cytopathogenesis in CEM cells.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID32367Percent protection of ATH8 cells from HIV-induced cytopathic effects at a concentration of 5 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (8.33)18.7374
1990's11 (91.67)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: 12.91

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 Index12.91 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index5.48 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.91)

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%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
uridine
[no description available]		1.9810uridinesdrug metabolite;
fundamental metabolite;
human metabolite
cytidine
[no description available]		1.9810cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae 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		2.3820dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
dideoxyadenosine
Dideoxyadenosine: 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 an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite.		1.9710adenosines;
purine 2',3'-dideoxyribonucleoside		EC 3.5.4.4 (adenosine deaminase) inhibitor;
EC 4.6.1.1 (adenylate cyclase) 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.		3.69100pyrimidine 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.		1.9810azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
lamivudine
[no description available]		1.9910monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
emtricitabine
Emtricitabine: A deoxycytidine analog and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B viruses. It is used to treat HIV INFECTIONS.. emtricitabine : An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2R,5S configuration). It is used in combination therapy for the treatment of HIV-1 infection.		1.9910monothioacetal;
nucleoside analogue;
organofluorine compound;
pyrimidone		antiviral drug;
HIV-1 reverse transcriptase inhibitor
2',3'-dideoxycytidinene
2',3'-dideoxycytidinene: 2',3'-unsaturated derivative of 2',3'-dideoxycytidine; potent inhibitor of HTLV-III in vitro; structure given in first source		2.3920
1-(2,3-dideoxy-2-fluoropentofuranosyl)cytosine
[no description available]		1.9810
elvucitabine
[no description available]		2.420
ConditionIndicatedRelationship StrengthStudiesTrials
Acquired Immune Deficiency Syndrome
[description not available]		01.9710
Acquired Immunodeficiency Syndrome
An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.		01.9710
HIV
Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.		03.2360
Leukemia L 1210
[description not available]		01.9810
Hepatitis B Virus Infection
[description not available]		01.9810
Hepatitis B
INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.		01.9810
Infections, Hepadnaviridae
[description not available]		01.9910
Hepadnaviridae Infections
Virus diseases caused by the HEPADNAVIRIDAE.		01.9910