Page last updated: 2024-12-07

2'-fluoro-2'-deoxyadenosine

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

2'-fluoro-2'-deoxyadenosine, also known as F-dAdo, is a synthetic nucleoside analog that has shown promise as an antiviral and anticancer agent. It is synthesized by fluorination of 2'-deoxyadenosine. F-dAdo acts as an inhibitor of viral DNA polymerases, including those of HIV, herpes simplex virus, and cytomegalovirus. It has also shown activity against certain types of cancer cells, including leukemia and lymphoma. F-dAdo is studied because of its potential therapeutic applications in the treatment of viral infections and cancer. Research on F-dAdo focuses on understanding its mechanism of action, improving its pharmacokinetic properties, and exploring its therapeutic potential in various disease models.

Cross-References

ID SourceID
PubMed CID100253
CHEMBL ID309579
SCHEMBL ID237404
MeSH IDM0097658

Synonyms (33)

Synonym
CHEMBL309579 ,
2'-beta-fluoro-2',3'-deoxyadenosine
(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol
64183-27-3
2'-deoxy-2'-fluoroadenosine
2'f-da
9-(2-fluoro-2-deoxy-beta-d-ribofuranosyl)-purin-6-amine
bdbm50144932
(2r,3r,4r,5r)-4-fluoro-2-hydroxymethyl-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-ol
(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
2'-fluoro-2'-deoxyadenosine
nsc 274941
adenosine, 2'-deoxy-2'-fluoro-
(2r,3r,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol
AKOS015900907
HG1028
SCHEMBL237404
6-amino-9-(2-deoxy-2-fluoro-beta-d-ribofuranosyl)-9h-purine
ZGYYPTJWJBEXBC-QYYRPYCUSA-N
9-(2-deoxy-2-fluoro-beta-d-ribofuranosyl)adenine
c10h12fn5o3
mfcd09750859
2 inverted exclamation marka-deoxy-2 inverted exclamation marka-fluoroadenosine
CS-0097284
AC-9552
2-fluoro-2-deoxyadenosine
AS-49376
DTXSID60982712
AMY31026
A851108
HY-W039442
PD158370
BP-58852

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The sensitivity of CLL cells to nine drugs (2'-chlorodeoxyadenosine, cisplatin, chlorambucil, cyclosporin A, doxorubicin, fludarabine, prednisolone, verapamil and vincristine) and two types of irradiation (gamma and UV-irradiation) was determined from dose-response curves of 4-day cultures ex vivo."( CD80 antigen expression as a predictor of ex vivo chemosensitivity in chronic lymphocytic leukemia.
Hulkkonen, J; Hurme, M; Kivekäs, I; Vilpo, J; Vilpo, L, 2002
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RNA-directed RNA polymerase IC50 (µMol)50.00000.01902.52798.8000AID86858
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histamine H1 receptorCavia porcellus (domestic guinea pig)EC50 (µMol)50.00000.00260.53341.2020AID86857
RNA-directed RNA polymerase EC50 (µMol)50.00000.00180.23482.8000AID86857
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID46752The cytotoxicity against CEM cells1997Journal of medicinal chemistry, Aug-15, Volume: 40, Issue:17
Synthesis and anti-hepatitis B virus activity of 9-(2-deoxy-2-fluoro-beta-L-arabinofuranosyl) purine nucleosides.
AID218762Antiviral activity against Influenza virus (A/Sweden/3/50/ (H1N1)) in dog kidney (MDCK) cells expressed.1993Journal of medicinal chemistry, Jan-08, Volume: 36, Issue:1
Purine 2'-deoxy-2'-fluororibosides as antiinfluenza virus agents.
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.
AID86377The cytotoxicity against HepG2 2.2.15 cells expressed as IC501997Journal of medicinal chemistry, Aug-15, Volume: 40, Issue:17
Synthesis and anti-hepatitis B virus activity of 9-(2-deoxy-2-fluoro-beta-L-arabinofuranosyl) purine nucleosides.
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.
AID86858Inhibition HCV NS5B-mediated RNA synthesis2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase.
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.
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.
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.
AID86373compound was tested in vitro for anti HBV activity in HepG2 2.2.15 cells1997Journal of medicinal chemistry, Aug-15, Volume: 40, Issue:17
Synthesis and anti-hepatitis B virus activity of 9-(2-deoxy-2-fluoro-beta-L-arabinofuranosyl) purine nucleosides.
AID662565Growth inhibition of Trichomonas vaginalis T1 at 100 uM after 24 hrs by hemocytometry2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
S-Adenosylhomocysteine hydrolase of the protozoan parasite Trichomonas vaginalis: potent inhibitory activity of 9-(2-deoxy-2-fluoro-β,D-arabinofuranosyl)adenine.
AID662566Growth inhibition of Trichomonas vaginalis T1 after 24 hrs by hemocytometry2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
S-Adenosylhomocysteine hydrolase of the protozoan parasite Trichomonas vaginalis: potent inhibitory activity of 9-(2-deoxy-2-fluoro-β,D-arabinofuranosyl)adenine.
AID218763Cytotoxicity in uninfected dog kidney (MDCK) cells.1993Journal of medicinal chemistry, Jan-08, Volume: 36, Issue:1
Purine 2'-deoxy-2'-fluororibosides as antiinfluenza virus agents.
AID86857Inhibition HCV RNA replication2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (30)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (20.00)18.7374
1990's5 (16.67)18.2507
2000's10 (33.33)29.6817
2010's7 (23.33)24.3611
2020's2 (6.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.79

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 Index18.79 (24.57)
Research Supply Index3.43 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.79)

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%
Other30 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]