Page last updated: 2024-12-07

3'-fluoro-3'-deoxyadenosine

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Description

3'-fluoro-3'-deoxyadenosine (3'-F-dAdo) is a nucleoside analog that has been investigated for its potential antiviral and anticancer properties. It is a synthetic compound that is structurally similar to adenosine, a naturally occurring nucleoside. The fluorine atom at the 3' position of the sugar moiety disrupts the normal function of the nucleoside, leading to its biological activity. 3'-F-dAdo has shown inhibitory activity against various viruses, including HIV and hepatitis C virus. It is also known to inhibit DNA polymerase and ribonucleotide reductase, enzymes involved in DNA synthesis and replication, thus contributing to its anticancer potential. The compound has been investigated for its ability to overcome drug resistance in cancer cells and is currently being explored in preclinical studies.'
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3'-fluoro-3'-deoxyadenosine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID122619
CHEMBL ID72928
SCHEMBL ID969050
MeSH IDM0174042

Synonyms (20)

Synonym
CHEMBL72928 ,
3'f-3'da
(2r,3s,4s,5r)-2-(6-aminopurin-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol
3'-fluoro-3'-deoxyadenosine
adenosine, 3'-deoxy-3'-fluoro-
75059-22-2
bdbm50144933
(2r,3s,4s,5r)-4-fluoro-5-hydroxymethyl-2-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-ol
3'-deoxy-3'-fluoroadenosine
(2r,3s,4s,5r)-2-(6-aminopurin-9-yl)-4-fluoro-5-(hydroxymethyl)oxolan-3-ol
3'-f-da
(2s,3r,4r,5s)-2-(6-amino-9h-purin-9-yl)-4-fluoro-5-(hydroxymethyl)-tetrahydrofuran-3-ol
DTXSID70226033
(2r,3s,4s,5r)-2-(6-amino-9h-purin-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol
SCHEMBL969050
AC-32287
AKOS027324855
mfcd20134043
F13576
DS-11561
[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)28.00000.01902.52798.8000AID86858
[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)1.20000.00260.53341.2020AID86857
RNA-directed RNA polymerase EC50 (µMol)1.20000.00180.23482.8000AID86857
[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 (33)

Assay IDTitleYearJournalArticle
AID218041Concentration (MIC), which is required to reduce virus-induced cytopathogenicity in African green monkey kidney (Vero B) cells against Sindbis virus1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
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.
AID1757145Antitrypanosomal activity against Trypanosoma cruzi Tulahuen CL2 infected in human MRC5 cells assessed as inhibition of parasite growth incubated for 7 days by chlorophenol red-fl-D-galactopyranoside based spectrophotometric analysis2021European journal of medicinal chemistry, Apr-15, Volume: 216Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.
AID1757142Antileishmanial activity against Leishmania infantum MHOM/MA(BE)/67 infected in mouse primary peritoneal macrophages treated 2 hrs post-infection and incubated for 5 days by Giemsa staining based microscopic analysis2021European journal of medicinal chemistry, Apr-15, Volume: 216Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.
AID218037Concentration (MIC), which is required to reduce virus-induced cytopathogenicity in African green monkey kidney (Vero B) cells against Coxsackie virus-B41991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID218040Concentration (MIC), which is required to reduce virus-induced cytopathogenicity in African green monkey kidney (Vero B) cells against forest virus1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
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.
AID1757148Selectivity index, ratio of EC50 for human MRC5 cells to EC50 for antitrypanosomal activity against Trypanosoma brucei brucei2021European journal of medicinal chemistry, Apr-15, Volume: 216Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.
AID91267Concentration required to reduce the viability of Human B-lymphoblast Raji cells1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID156711Concentration (MIC), required to reduce virus-induced cytopathogenicity in HeLa cells of Primary rabbit kidney (PRK ) cells against Vesicular stomatitis virus type 11991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID87150Concentration (MIC), which is required to reduce virus-induced cytopathogenicity in HeLa cells against Polio virus type-11991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID156717Concentration (MIC)required to reduce virus-induced cytopathogenicity in Primary rabbit kidney (PRK ) cells against HSV-1 with a strain KOS1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
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.
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.
AID1757141Cytotoxicity against mouse primary macrophage cells assessed as reduction in cell viability2021European journal of medicinal chemistry, Apr-15, Volume: 216Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.
AID156839Concentration (MIC)required to reduce virus-induced cytopathogenicity in Primary rabbit kidney (PRK ) cells against HSV-2 with a strain G1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID218042Concentration (MIC), which is required to reduce virus-induced cytopathogenicity in African green monkey kidney (Vero B) cells against para-influenza virus-31991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID89805Concentration required to reduce the viability of Human T-lymphoblast MT-4 cells1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID218034Concentration (MCC) required to cause a microscopically detectable alteration of normal cell morphology, African green monkey kidney (Vero B) cells1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID156714Concentration (MIC), required to reduce virus-induced cytopathogenicity in Primary rabbit kidney (PRK ) cells against Vesicular stomatitis virus type 21991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID1167621Antiviral activity against Hepatitis C virus infected in mouse HB-1 cells after 24 hrs by ribonuclease replicon assay2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Synthesis of 3',4'-difluoro-3'-deoxyribonucleosides and its evaluation of the biological activities: discovery of a novel type of anti-HCV agent 3',4'-difluorocordycepin.
AID142337Concentration required to reduce the viability of Murine leukemia L1210 cells1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID1757144Cytotoxicity against human MRC5 cells assessed as reduction in cell viability after 3 days by resazurin dye based fluorimetric analysis2021European journal of medicinal chemistry, Apr-15, Volume: 216Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.
AID89806Concentration required to reduce the viability of Human T-lymphoblast Molt/4F cells1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID1757147Antitrypanosomal activity against Trypanosoma brucei rhodesiense assessed as parasite growth inhibition2021European journal of medicinal chemistry, Apr-15, Volume: 216Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.
AID218039Concentration (MIC), which is required to reduce virus-induced cytopathogenicity in African green monkey kidney (Vero B) cells against Reo-virus-11991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID156695Concentration (MCC) required to cause a microscopically detectable alteration of normal cell morphology, in Primary rabbit kidney (PRK) cells1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID1757140Selectivity index, ratio of EC50 for cytotoxicity against mouse primary macrophage to EC50 for antileishmanial activity against Leishmania infantum MHOM/MA(BE)/67 infected in mouse primary peritoneal macrophages2021European journal of medicinal chemistry, Apr-15, Volume: 216Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.
AID1757143Selectivity index, ratio of EC50 for cytotoxicity against human MRC5 cells to EC50 for antitrypanosomal activity against Trypanosoma cruzi Tulahuen CL2 infected in human MRC5 cells2021European journal of medicinal chemistry, Apr-15, Volume: 216Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.
AID87138Concentration (MCC) required to cause a microscopically detectable alteration of normal cell morphology, in HeLa cells1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID1757139Antitrypanosomal activity against Trypanosoma brucei brucei assessed as parasite growth inhibition2021European journal of medicinal chemistry, Apr-15, Volume: 216Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.
AID156716Concentration (MIC), which is required to reduce virus-induced cytopathogenicity in Primary rabbit kidney (PRK ) cells against Vaccinia virus1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases.
AID1757149Selectivity index, ratio of EC50 for human MRC5 cells to EC50 for antitrypanosomal activity against Trypanosoma brucei rhodesiense2021European journal of medicinal chemistry, Apr-15, Volume: 216Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (9.09)18.7374
1990's4 (36.36)18.2507
2000's2 (18.18)29.6817
2010's2 (18.18)24.3611
2020's2 (18.18)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.59

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 Index12.59 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.59)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]