Page last updated: 2024-11-06

5-chloro-2'-deoxyuridine

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

5-Chloro-2'-deoxyuridine (CldU) is a synthetic nucleoside analog that is structurally similar to thymidine. It is a potent inhibitor of DNA synthesis and is used in research as a tool to study cell proliferation. CldU is incorporated into DNA during replication, replacing thymidine. This incorporation can be detected using antibodies specific to CldU, allowing researchers to track cell division and proliferation. CldU is also used in conjunction with other techniques, such as immunofluorescence microscopy, to study DNA replication and repair processes. CldU has shown promise as a potential therapeutic agent for various diseases, including cancer, autoimmune diseases, and viral infections. However, further research is needed to evaluate its safety and efficacy.'

Cross-References

ID SourceID
PubMed CID65510
CHEMBL ID505732
SCHEMBL ID1469771
MeSH IDM0059158

Synonyms (24)

Synonym
5-chloro-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
5-chloro-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1h-pyrimidine-2,4-dione
5-chloro-durd
C15889
5-chloro-2 -deoxyuridine
5-chloro-2'-deoxyuridine
5-chlorodeoxyuridine
chlorodeoxyuridine
brn 0546807
bdbm50246637
5-chloro-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
CHEMBL505732 ,
SCHEMBL1469771
nsc 749426
cldu
AKOS027447511
CS-0059203
HY-112669
NJCXGFKPQSFZIB-RRKCRQDMSA-N
5-chloro-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
DTXSID50964486
5-chloro-1-(2-deoxypentofuranosyl)-4-hydroxypyrimidin-2(1h)-one
MS-23705
mfcd00006531

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" This work led us to propose a model in which the human DNA helicase RECQ1 acts as a governor of the single-stranded DNA binding protein RPA and regulates its bioavailability for DNA synthesis."( Single-Molecule DNA Fiber Analyses to Characterize Replication Fork Dynamics in Living Cells.
Banerjee, T; Brosh, RM; Datta, A; Dhar, S, 2019
)
0.51
" 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
[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)
Thymidylate kinaseMycobacterium tuberculosis H37RvKi10.00004.50008.500010.0000AID408386
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine phosphorylaseHomo sapiens (human)Km186.00000.16000.16000.1600AID211066
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
mitochondrial genome maintenanceThymidine phosphorylaseHomo sapiens (human)
angiogenesisThymidine phosphorylaseHomo sapiens (human)
pyrimidine nucleobase metabolic processThymidine phosphorylaseHomo sapiens (human)
pyrimidine nucleoside metabolic processThymidine phosphorylaseHomo sapiens (human)
chemotaxisThymidine phosphorylaseHomo sapiens (human)
signal transductionThymidine phosphorylaseHomo sapiens (human)
cell differentiationThymidine phosphorylaseHomo sapiens (human)
regulation of myelinationThymidine phosphorylaseHomo sapiens (human)
dTMP catabolic processThymidine phosphorylaseHomo sapiens (human)
regulation of transmission of nerve impulseThymidine phosphorylaseHomo sapiens (human)
regulation of gastric motilityThymidine phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
1,4-alpha-oligoglucan phosphorylase activityThymidine phosphorylaseHomo sapiens (human)
protein bindingThymidine phosphorylaseHomo sapiens (human)
growth factor activityThymidine phosphorylaseHomo sapiens (human)
thymidine phosphorylase activityThymidine phosphorylaseHomo sapiens (human)
protein homodimerization activityThymidine phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

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

Bioassays (31)

Assay IDTitleYearJournalArticle
AID1135478Antiviral activity against Vaccinia virus infected in human skin fibroblasts assessed as inhibition of virus-induced cytopathogenicity1977Journal of medicinal chemistry, Jul, Volume: 20, Issue:7
Improved synthesis and in vitro antiviral activities of 5-cyanouridine and 5-cyano-2'-deoxyuridine.
AID99530In vitro growth inhibition of L5178Y-Parental murine leukemia cells2000Journal of medicinal chemistry, Nov-30, Volume: 43, Issue:24
5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID1135481Antiviral activity against Herpes simplex virus 1 infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity1977Journal of medicinal chemistry, Jul, Volume: 20, Issue:7
Improved synthesis and in vitro antiviral activities of 5-cyanouridine and 5-cyano-2'-deoxyuridine.
AID98529Evaluation of antitumor activity against mutant murine leukemia L1210 cells1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID90595In vitro antiviral activity against Human cytomegalovirus (HCMV) was determined; ND= Not determined2002Bioorganic & medicinal chemistry letters, Feb-11, Volume: 12, Issue:3
5-Bromo (or chloro)-6-azido-5,6-dihydro-2' -deoxyuridine and -thymidine derivatives with potent antiviral activity.
AID99532In vitro growth inhibition of L5178Y-Parental murine leukemia cells by incorporation of [14C]-Thd.2000Journal of medicinal chemistry, Nov-30, Volume: 43, Issue:24
5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID408386Inhibition of Mycobacterium tuberculosis recombinant TMPK2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
Substituted benzyl-pyrimidines targeting thymidine monophosphate kinase of Mycobacterium tuberculosis: synthesis and in vitro anti-mycobacterial activity.
AID87507Evaluation of antiviral activity against Herpes simplex virus type 1 (HSV-1) strain KOS.1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID1135479Antiviral activity against Herpes simplex virus 1 infected in human skin fibroblasts assessed as inhibition of virus-induced cytopathogenicity1977Journal of medicinal chemistry, Jul, Volume: 20, Issue:7
Improved synthesis and in vitro antiviral activities of 5-cyanouridine and 5-cyano-2'-deoxyuridine.
AID98532Evaluation of cytostatic activity by using antitumor assays against murine leukemia L1210 cells1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID87181In vitro antiviral activity against Herpes simplex virus (HSV-2) was determined; ND= Not determined2002Bioorganic & medicinal chemistry letters, Feb-11, Volume: 12, Issue:3
5-Bromo (or chloro)-6-azido-5,6-dihydro-2' -deoxyuridine and -thymidine derivatives with potent antiviral activity.
AID218132Evaluation of antiviral activity against Vaccinia virus1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID99533In vitro growth inhibition of FdUrd resistant L5178Y-Resistant murine leukemia cells2000Journal of medicinal chemistry, Nov-30, Volume: 43, Issue:24
5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID46568In vitro anti-HIV screen using HIV-1 infected CD4 lymphocytes (CEM cell line), determines cytotoxicity; ND= Not determined2002Bioorganic & medicinal chemistry letters, Feb-11, Volume: 12, Issue:3
5-Bromo (or chloro)-6-azido-5,6-dihydro-2' -deoxyuridine and -thymidine derivatives with potent antiviral activity.
AID87828Evaluation of antiviral activity against Herpes simplex virus type 2 (HSV-2) strain Lyons1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID216460In vitro antiviral activity against Varicella zoster virus (VZV) was determined; ND= Not determined2002Bioorganic & medicinal chemistry letters, Feb-11, Volume: 12, Issue:3
5-Bromo (or chloro)-6-azido-5,6-dihydro-2' -deoxyuridine and -thymidine derivatives with potent antiviral activity.
AID409958Inhibition of bovine brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID70228In vitro antiviral activity against Epstein Barr virus (EBV) was determined; ND= Not determined2002Bioorganic & medicinal chemistry letters, Feb-11, Volume: 12, Issue:3
5-Bromo (or chloro)-6-azido-5,6-dihydro-2' -deoxyuridine and -thymidine derivatives with potent antiviral activity.
AID1135480Antiviral activity against Vaccinia virus infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity1977Journal of medicinal chemistry, Jul, Volume: 20, Issue:7
Improved synthesis and in vitro antiviral activities of 5-cyanouridine and 5-cyano-2'-deoxyuridine.
AID87508Evaluation of antiviral activity against Herpes simplex virus type 1 (HSV-1) strain McIntyre1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID87826Evaluation of antiviral activity against Herpes simplex virus type 2 (HSV-2) strain 196.1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID221339Evaluation for antitumor activity against human lymphoblast Raji cells1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID232840Ratio of Vmax to that of dThd (Vmax = 0.14)1980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
Thymidine phosphorylase. Substrate specificity for 5-substituted 2'-deoxyuridines.
AID87506Evaluation of antiviral activity against Herpes simplex virus type 1 (HSV-1) strain F1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID216539Evaluation of antiviral activity against Vesicular stomatitis virus.1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID87827Evaluation of antiviral activity against Herpes simplex virus type 2 (HSV-2) strain G1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID220992Evaluation of antitumor activity against thymidine kinase deficient Raji cell line1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID87188In vitro antiviral activity against Herpes simplex virus (HSV-1) was determined2002Bioorganic & medicinal chemistry letters, Feb-11, Volume: 12, Issue:3
5-Bromo (or chloro)-6-azido-5,6-dihydro-2' -deoxyuridine and -thymidine derivatives with potent antiviral activity.
AID46576Inhibitory concentration for spectrum antiviral activity against herpes viruses; ND= Not determined2002Bioorganic & medicinal chemistry letters, Feb-11, Volume: 12, Issue:3
5-Bromo (or chloro)-6-azido-5,6-dihydro-2' -deoxyuridine and -thymidine derivatives with potent antiviral activity.
AID211066Michaelis-Menten constant (Km) against horse liver thymidine phosphorylase1980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
Thymidine phosphorylase. Substrate specificity for 5-substituted 2'-deoxyuridines.
AID99531In vitro growth inhibition of L5178Y-Parental murine leukemia cells by incorporation of [14C]Leu.2000Journal of medicinal chemistry, Nov-30, Volume: 43, Issue:24
5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (72)

TimeframeStudies, This Drug (%)All Drugs %
pre-199021 (29.17)18.7374
1990's18 (25.00)18.2507
2000's19 (26.39)29.6817
2010's13 (18.06)24.3611
2020's1 (1.39)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.35

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 Index19.35 (24.57)
Research Supply Index4.34 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.35)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.32%)6.00%
Case Studies1 (1.32%)4.05%
Observational0 (0.00%)0.25%
Other74 (97.37%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]