Page last updated: 2024-12-08

5-ethynyl-2'-deoxyuridine

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

Description

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

Cross-References

ID SourceID
PubMed CID472172
CHEMBL ID222932
SCHEMBL ID868882
MeSH IDM0097927

Synonyms (32)

Synonym
61135-33-9
5-ethynyl-durd
5-ethynyl-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
5-ethynyl-2'-deoxyuridine
2'-deoxy-5-ethynyluridine
brn 0756841
uridine, 2'-deoxy-5-ethynyl-
CHEMBL222932
CDEURGJCGCHYFH-DJLDLDEBSA-N
2'deoxy-5-ethynyluridine
unii-g373s00w2j
g373s00w2j ,
S1661
SCHEMBL868882
5-ethynyl-2'-du
J-700091
J-700347
AC-32360
AKOS024462948
AS-59368
5-ethynyl-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
5-ethynyl-2'-deoxyuridine, (edu), aldrichcpr
5-ethynyl-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
Q4639590
edu (ethynyldeoxyuridine)
DTXSID20976652
C75857
edu (5-ethynyl-2'-deoxyuridine)
HY-118411
CS-0065850
GLXC-26691
BP-54302

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Our results demonstrate that elevated concentrations (similar to manufacturers suggested concentration; >5-10 μM) of EdU treatment were toxic to the cell cultures, particularly in cells with a defect in homologous recombination repair."( Evaluating the Genotoxic and Cytotoxic Effects of Thymidine Analogs, 5-Ethynyl-2'-Deoxyuridine and 5-Bromo-2'-Deoxyurdine to Mammalian Cells.
Allum, AJ; Froning, CE; Haskins, AH; Haskins, JS; Kato, TA; Maeda, J; Su, C; Walsh, KD, 2020
)
0.79

Bioavailability

ExcerptReferenceRelevance
" Flow cytometry detected the EdU incorporation, representing the bioavailability of EdU."( In Vivo Labeling and Tracking of Proliferating Corneal Endothelial Cells by 5-Ethynyl-2'-Deoxyuridine in Rabbits.
Correll, MH; Crouzet, E; de la Cour, MD; Gain, P; He, Z; Heegaard, S; Kiilgaard, JF; Thuret, G; Udsen, MS, 2021
)
0.85
" To date, using a variety of methods, only the bioavailability time of tritiated thymidine and 5-bromo-2'-deoxyuridine (BrdU) have been evaluated."( The bioavailability time of commonly used thymidine analogues after intraperitoneal delivery in mice: labeling kinetics in vivo and clearance from blood serum.
Belousov, VV; Enikolopov, GN; Maltsev, DI; Mellanson, KA; Podgorny, OV, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
"Labeling of ADSC was examined for the dosage effect of EdU and stability of label by Alexa-594 staining followed by fluorescence microscopy."( Labeling and tracking of mesenchymal stromal cells with EdU.
Banie, L; Huang, YC; Lin, CS; Lin, G; Lue, TF; Shindel, AW; Wang, G, 2009
)
0.35
"At the recommended dosage of 10(-8) mol/L, EdU is non-toxic to ADSCs."( Effects of EdU labeling on mesenchymal stem cells.
Albersen, M; Lin, CS; Lin, G; Lue, TF; Ning, H, 2013
)
0.39
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (42)

Assay IDTitleYearJournalArticle
AID165542Inhibitory activity against incorporation of deoxy-[1',2'-3H]uridine (dUrd) into the DNA of uninfected primary rabbit kidney (PRK) cell cultures1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides.
AID165528Concentration required to reduce Vaccinia virus induced cytopathogenicity in primary rabbit kidney (PRK) cell cultures1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides.
AID288921Antiviral activity against HCMV AD169 in HEL cells assessed as reduction of virus plaque formation2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288936Inhibition of proliferation of thymidine kinase deficient mouse FM3A cells expressing HSV1 thymidine kinase2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID306768Cytotoxicity against human MDA-MB-231 cells after 72 hrs2007Bioorganic & medicinal chemistry, Apr-15, Volume: 15, Issue:8
5-Alkynyl-2'-deoxyuridines: chromatography-free synthesis and cytotoxicity evaluation against human breast cancer cells.
AID112441Inhibitory activity against incorporation of deoxy-[methyl.3H-]-thymidine (dThd) into the DNA of murine leukemia L1210 cell cultures1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides.
AID288923Cytotoxicity against HEL cells assessed as alteration in cell morphology2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288935Inhibition of proliferation of thymidine kinase deficient mouse FM3A cells2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288940Inhibition of proliferation of VZV thymidine kinase expressing OSTtk-/VZVtk+ -b cells2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288939Inhibition of proliferation of VZV thymidine kinase expressing OSTtk-/VZVtk+ -a cells2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID306767Cytotoxicity against human MCF7 cells after 72 hrs2007Bioorganic & medicinal chemistry, Apr-15, Volume: 15, Issue:8
5-Alkynyl-2'-deoxyuridines: chromatography-free synthesis and cytotoxicity evaluation against human breast cancer cells.
AID141365Effect on mutant line lacking dThd kinase (S49/TK at 0.1 mM; No effect1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Inhibition of thymidylate synthetase by 5-alkynyl-2'-deoxyuridylates.
AID85559Concentration required to reduce the number of viral plaques in vivo cell monolayers of herpes simplex virus type 1.1989Journal of medicinal chemistry, Feb, Volume: 32, Issue:2
Synthesis and antiviral activity of phosphonoacetic and phosphonoformic acid esters of 5-bromo-2'-deoxyuridine and related pyrimidine nucleosides and acyclonucleosides.
AID165543Inhibitory activity against incorporation of deoxy-[methyl.3H-]-thymidine (dThd) into the DNA of uninfected primary rabbit kidney (PRK) cell cultures1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides.
AID288925Antiviral activity against TK+ VZV OKA in HEL cells assessed as reduction of virus plaque formation2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288919Antiviral activity against thymidine kinase-deficient HSV1 B2006 in E6SM cells assessed as reduction of virus-induced cytopathogenicity2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID280941Cytotoxicity against mouse L1210/0 cells after 48 hrs2007Journal of medicinal chemistry, Apr-05, Volume: 50, Issue:7
Probing the anticancer activity of nucleoside analogues: a QSAR model approach using an internally consistent training set.
AID288916Antiviral activity against HSV1 KOS in E6SM cells assessed as reduction of virus-induced cytopathogenicity2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288942Antiviral activity against Coxsackie virus B4 in HeLa cells at 40 to >400 ug/mL2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288926Antiviral activity against TK+ VZV YS in HEL cells assessed as reduction of virus plaque formation2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288922Antiviral activity against HCMV Davis in HEL cells assessed as reduction of virus plaque formation2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288927Antiviral activity against thymidine kinase deficient VZV 07/1 in HEL cells assessed as reduction of virus plaque formation2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288947Antiviral activity against Punta Toro virus in vero cells assessed as reduction of virus-induced cytopathicity at 20 to >400 ug/mL2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288915Cytotoxicity against E6SM cells assessed as alteration in cell morphology2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288917Antiviral activity against HSV2 G in E6SM cells assessed as reduction of virus-induced cytopathogenicity2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288934Inhibition of proliferation of mouse FM3A/O cells2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID165526Concentration required to reduce Herpes simplex virus type 1 induced cytopathogenicity in primary rabbit kidney (PRK) cell cultures1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides.
AID288924Cytotoxicity against HEL cells2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288918Antiviral activity against Vaccinia virus in E6SM cells assessed as reduction of virus-induced cytopathogenicity2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288945Antiviral activity against Reovirus1 in vero cells assessed as reduction of virus-induced cytopathicity at 40 to >400 ug/mL2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288920Antiviral activity against thymidine kinase deficient HSV1 VMW1837 in E6SM cells assessed as reduction of virus-induced cytopathogenicity2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288928Antiviral activity against thymidine kinase deficient VZV YS in HEL cells assessed as reduction of virus plaque formation2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288938Inhibition of proliferation of thymidine kinase deficient OST cells2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID219246Effective concentration to inhibit the growth of Wild-type S49 cells1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Inhibition of thymidylate synthetase by 5-alkynyl-2'-deoxyuridylates.
AID165527Concentration required to reduce Herpes simplex virus type 2 induced cytopathogenicity in primary rabbit kidney (PRK) cell cultures1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides.
AID84605Concentration required to reduce the number of viral plaques in vivo cell monolayers of herpes simplex virus type 2.1989Journal of medicinal chemistry, Feb, Volume: 32, Issue:2
Synthesis and antiviral activity of phosphonoacetic and phosphonoformic acid esters of 5-bromo-2'-deoxyuridine and related pyrimidine nucleosides and acyclonucleosides.
AID288943Antiviral activity against Respiratory syncytial virus in HeLa cells at 40 to >400 ug/mL2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288946Antiviral activity against Sindbis virus in vero cells assessed as reduction of virus-induced cytopathicity at 40 to >400 ug/mL2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID112423Concentration required to reduce leukemia L1210 cell growth in mice1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides.
AID288944Antiviral activity against Parainfluenza 3 virus in vero cells assessed as reduction of virus-induced cytopathicity at 20 to >400 ug/mL2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288941Antiviral activity against VSV in HeLa cells at 40 to >400 ug/mL2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
AID288937Inhibition of proliferation of thymidine kinase deficient mouse FM3A cells expressing HSV2 thymidine kinase2007Journal of medicinal chemistry, Jun-14, Volume: 50, Issue:12
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (199)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (2.01)18.7374
1990's0 (0.00)18.2507
2000's15 (7.54)29.6817
2010's152 (76.38)24.3611
2020's28 (14.07)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 38.52

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

MetricThis Compound (vs All)
Research Demand Index38.52 (24.57)
Research Supply Index5.31 (2.92)
Research Growth Index5.29 (4.65)
Search Engine Demand Index53.09 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (38.52)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (0.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other200 (99.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]