Page last updated: 2024-11-07

2'-fluoro-2'-deoxycytidine

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

2'-fluoro-2'-deoxycytidine (F-dCyd) is a synthetic nucleoside analog that is structurally similar to the natural nucleoside cytidine. It is a potent inhibitor of DNA polymerase and is used as an antiviral agent. F-dCyd is incorporated into DNA during replication, where it can terminate DNA chain elongation. This is due to the fluorine atom, which replaces a hydrogen atom at the 2' position of the deoxyribose sugar, making it difficult for the polymerase to add the next nucleotide. F-dCyd has been shown to be effective against a variety of viruses, including herpes simplex virus (HSV), cytomegalovirus (CMV), and Epstein-Barr virus (EBV). It is also being investigated for its potential use in the treatment of cancer. The compound has been studied extensively due to its ability to inhibit DNA polymerase and its therapeutic potential. It is often investigated in the context of developing new antiviral and anticancer therapies. Studies focus on its mechanisms of action, its efficacy, and its potential side effects.'

Cross-References

ID SourceID
PubMed CID101507
CHEMBL ID374528
SCHEMBL ID233120
MeSH IDM0050324

Synonyms (38)

Synonym
nsc529432
10212-20-1
nsc-529432
cytidine, 2'-deoxy-2'-fluoro-
2'-deoxy-2'-fluorocytidine ,
4-amino-1-[(2r,3r,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
FDC ,
3-[(2r,3r,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-amino-3-hydropyrimidin-2-one
.beta.-d-2'-deoxy-2'-fluorocytidine
2'-fluoro-2'-deoxycytidine
2'deoxy-2'-fluorocytidine
CHEMBL374528
4-amino-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
4-amino-1-[(2r,3r,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
unii-lcy080jpy9
lcy080jpy9 ,
nsc 529432
2-deoxy-2-fluorocytidine
AKOS015896915
AKOS015854842
HG1103
2'-deoxy-2'-fluoro cytidine
SCHEMBL233120
2'-fluoro-2'-deoxy-.beta.-d-ribofuranosylcytosine
2'-deoxy-2'-(r)-fluoro-cytidine
NVZFZMCNALTPBY-XVFCMESISA-N
4-amino-1-((2r,3r,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1h)-one
mfcd00057445
4-amino-1-[(2r,3r,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
AS-59691
Z3234821490
NCGC00370855-01
Q27282917
2'-fluoro-2'- deoxycytidine
EN300-7382371
CS-W012725
HY-W012009
BP-58853

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Rats were dosed intravenously with either 2'-fluorouridine (2'-FU) or 2'-fluorocytidine (2'-FC) at doses of 5, 50, and 500 mg/kg/day for 90 days."( Quantification of 2'-fluoro-2'-deoxyuridine and 2'-fluoro-2'-deoxycytidine in DNA and RNA isolated from rats and woodchucks using LC/MS/MS.
Bendele, RA; Koc, H; Lehrman, SR; Richardson, FC; Richardson, KA; Swenberg, JA; Zhang, C, 2002
)
0.57
"038) similar to the results obtained in the H5N1 infection model using a similar dosing regimen (50%, p<0."( In vitro and in vivo efficacy of fluorodeoxycytidine analogs against highly pathogenic avian influenza H5N1, seasonal, and pandemic H1N1 virus infections.
Barnard, DL; Day, CW; Kumaki, Y; Morrey, JD; Smee, DF, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Deoxycytidine kinaseHomo sapiens (human)Km4.70000.40003.57908.5000AID278932
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (13)

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)
cell surface receptor signaling pathwayCytidine deaminaseHomo sapiens (human)
pyrimidine-containing compound salvageCytidine deaminaseHomo sapiens (human)
cytidine deaminationCytidine deaminaseHomo sapiens (human)
cytosine metabolic processCytidine deaminaseHomo sapiens (human)
negative regulation of cell growthCytidine deaminaseHomo sapiens (human)
UMP salvageCytidine deaminaseHomo sapiens (human)
negative regulation of nucleotide metabolic processCytidine deaminaseHomo sapiens (human)
response to cycloheximideCytidine deaminaseHomo sapiens (human)
cellular response to external biotic stimulusCytidine deaminaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

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)
nucleoside bindingCytidine deaminaseHomo sapiens (human)
cytidine deaminase activityCytidine deaminaseHomo sapiens (human)
protein bindingCytidine deaminaseHomo sapiens (human)
zinc ion bindingCytidine deaminaseHomo sapiens (human)
identical protein bindingCytidine deaminaseHomo sapiens (human)
protein homodimerization activityCytidine deaminaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
nucleoplasmDeoxycytidine kinaseHomo sapiens (human)
cytosolDeoxycytidine kinaseHomo sapiens (human)
mitochondrionDeoxycytidine kinaseHomo sapiens (human)
cytoplasmDeoxycytidine kinaseHomo sapiens (human)
extracellular regionCytidine deaminaseHomo sapiens (human)
cytosolCytidine deaminaseHomo sapiens (human)
secretory granule lumenCytidine deaminaseHomo sapiens (human)
tertiary granule lumenCytidine deaminaseHomo sapiens (human)
ficolin-1-rich granule lumenCytidine deaminaseHomo sapiens (human)
cytosolCytidine deaminaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID306697Cytostatic activity against human 2209-23 cells2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479.
AID1204708Inhibition of RSV A2 RNA-dependent RNA polymerase expressed in human Hep2 cells using ATP, GTP, UTP, CTP and 1.5 uCi [alpha-32P] NTP as substrate assessed as reduction of total radiolabled transcript after 90 mins by agarose gel electrophoresis2015Bioorganic & medicinal chemistry letters, Jun-15, Volume: 25, Issue:12
Discovery of β-D-2'-deoxy-2'-α-fluoro-4'-α-cyano-5-aza-7,9-dideaza adenosine as a potent nucleoside inhibitor of respiratory syncytial virus with excellent selectivity over mitochondrial RNA and DNA polymerases.
AID1204707Antiviral activity against RSV A2 infected in human Hep2 cells assessed as protection against virus-induced cytopathic effect after 4 days by Cell-Titer Glo assay2015Bioorganic & medicinal chemistry letters, Jun-15, Volume: 25, Issue:12
Discovery of β-D-2'-deoxy-2'-α-fluoro-4'-α-cyano-5-aza-7,9-dideaza adenosine as a potent nucleoside inhibitor of respiratory syncytial virus with excellent selectivity over mitochondrial RNA and DNA polymerases.
AID493450Cytotoxicity against human HuH7 cells by MTS assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Synthesis and anti-HCV activity of 3',4'-oxetane nucleosides.
AID750143Inhibition of HCV 1b NS5b polymerase2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
Evaluation of 2'-α-fluorine modified nucleoside phosphonates as potential inhibitors of HCV polymerase.
AID493448Antiviral activity against HCV 1a infected in human HB-1 cells assessed as inhibition of viral RNA replication after 24 hrs2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Synthesis and anti-HCV activity of 3',4'-oxetane nucleosides.
AID1758995Selectivity index, ratio of EC50 for antiviral activity against Measles virus infected in African green monkey Vero cells to CC50 for African green monkey Vero cells2021Bioorganic & medicinal chemistry letters, 06-01, Volume: 41Enantiomeric 4'-truncated 6'-fluoro-3-deazaneplanocin and its 3-bromo derivative: Synthesis and antiviral properties, including Ebola and Marburg.
AID1204711Cytotoxicity against human MT4 cells assessed as cell viability after 5 days by Cell-Titer Glo assay2015Bioorganic & medicinal chemistry letters, Jun-15, Volume: 25, Issue:12
Discovery of β-D-2'-deoxy-2'-α-fluoro-4'-α-cyano-5-aza-7,9-dideaza adenosine as a potent nucleoside inhibitor of respiratory syncytial virus with excellent selectivity over mitochondrial RNA and DNA polymerases.
AID431226Activity of cloned cytidine deaminase in human HuH7 cells by spectrophotometric analysis2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID278932Activity of human dCK expressed in HepG2 cells assessed as phosphorylation by coupled enzyme assay2007Antimicrobial agents and chemotherapy, Feb, Volume: 51, Issue:2
Mechanism of activation of beta-D-2'-deoxy-2'-fluoro-2'-c-methylcytidine and inhibition of hepatitis C virus NS5B RNA polymerase.
AID1758994Antiviral activity against Measles virus infected in African green monkey Vero cells by neutral red assay2021Bioorganic & medicinal chemistry letters, 06-01, Volume: 41Enantiomeric 4'-truncated 6'-fluoro-3-deazaneplanocin and its 3-bromo derivative: Synthesis and antiviral properties, including Ebola and Marburg.
AID1204709Inhibition of human mitochondrial RNA polymerase using 5'-32P-R12/D18 as RNA/DNA template assessed as single nucleotide incorporation rate at 500 uM after 0.17 to 30 mins by PAGE analysis2015Bioorganic & medicinal chemistry letters, Jun-15, Volume: 25, Issue:12
Discovery of β-D-2'-deoxy-2'-α-fluoro-4'-α-cyano-5-aza-7,9-dideaza adenosine as a potent nucleoside inhibitor of respiratory syncytial virus with excellent selectivity over mitochondrial RNA and DNA polymerases.
AID431228Ratio of Kcat to Km for cloned cytidine deaminase in human HuH7 cells by spectrophotometric analysis2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID278933Ratio of Kcat to Km for human dCK expressed in HepG2 cells2007Antimicrobial agents and chemotherapy, Feb, Volume: 51, Issue:2
Mechanism of activation of beta-D-2'-deoxy-2'-fluoro-2'-c-methylcytidine and inhibition of hepatitis C virus NS5B RNA polymerase.
AID306695Antiviral activity against HCV 1b replicon in human 2209-23 cells2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479.
AID306696Cytotoxicity against human 2209-23 cells2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479.
AID1204710Inhibition of human mitochondrial DNA polymerase gamma large subunit/DNA polymerase gamma accessory subunit using 32P-D19/D36 as DNA primer/template assessed as single nucleotide incorporation rate at 100 uM after 5 to 90 mins by PAGE analysis relative to2015Bioorganic & medicinal chemistry letters, Jun-15, Volume: 25, Issue:12
Discovery of β-D-2'-deoxy-2'-α-fluoro-4'-α-cyano-5-aza-7,9-dideaza adenosine as a potent nucleoside inhibitor of respiratory syncytial virus with excellent selectivity over mitochondrial RNA and DNA polymerases.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (12.00)18.7374
1990's1 (4.00)18.2507
2000's7 (28.00)29.6817
2010's9 (36.00)24.3611
2020's5 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.09

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.09 (24.57)
Research Supply Index3.30 (2.92)
Research Growth Index5.31 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.09)

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%
Other26 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]