Compounds > carbocyclic 5-iodo-2'-deoxyuridine
Page last updated: 2024-12-07

carbocyclic 5-iodo-2'-deoxyuridine

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

Cross-References

ID SourceID
PubMed CID459905
CHEMBL ID2311131
SCHEMBL ID3411578
MeSH IDM0175155

Synonyms (8)

Synonym
c-idu
(+)-c-idu
2,4(1h,3h)-pyrimidinedione,1-[3-hydroxy-4-(hydroxymethyl)- cyclopentyl]-5-iodo-, (1alpha,3beta,4alpha)-(+ -)-
1-[(1r,3s,4r)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]-5-iodo-pyrimidine-2,4-dione
1-[(1r,3s,4r)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]-5-iodopyrimidine-2,4-dione
bdbm50422566
CHEMBL2311131 ,
SCHEMBL3411578
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine kinase, cytosolicHomo sapiens (human)Ki0.21000.09001.52137.0000AID210688
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (6)

Processvia Protein(s)Taxonomy
nucleobase-containing compound metabolic processThymidine kinase, cytosolicHomo sapiens (human)
deoxyribonucleoside monophosphate biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine metabolic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
protein homotetramerizationThymidine kinase, cytosolicHomo sapiens (human)
DNA synthesis involved in mitotic DNA replicationThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
thymidine kinase activityThymidine kinase, cytosolicHomo sapiens (human)
protein bindingThymidine kinase, cytosolicHomo sapiens (human)
ATP bindingThymidine kinase, cytosolicHomo sapiens (human)
zinc ion bindingThymidine kinase, cytosolicHomo sapiens (human)
identical protein bindingThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

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

Bioassays (42)

Assay IDTitleYearJournalArticle
AID161455Antiviral activity against KOS strain of herpes simplex virus-1 in primary rabbit kidney cell cultures1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine.
AID85093Antiviral activity against herpes simplex virus(2) strain MS expressed as virus rating. Experiment 11983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
AID161454Antiviral activity against G strain of herpes simplex virus-2 in primary rabbit kidney cell cultures1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine.
AID210688Binding affinity constant against HSV-1 thymidine kinase2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
Synthesis and biological evaluation of 5-substituted derivatives of the potent antiherpes agent (north)-methanocarbathymine.
AID84063Antiviral activity against herpes simplex virus(1) strain 377, expressed as virus rating. Experiment 11983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
AID87639Minimum inhibitory concentration (MIC) required to reduce thymidine kinase deficient HSV-1 induced cytopathogenicity in primary rabbit kidney cell cultures1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID84967Minimum inhibitory concentration (MIC50) in Herpes simplex virus type-2 (HSV-2) using MS strain. Experiment 11983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
AID161459Antiviral activity against Vaccinia virus in primary rabbit kidney cell cultures1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine.
AID93931Minimum inhibitory concentration (MIC) required to inhibit proliferation of murine leukemia L1210 (wild type)1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID161457Antiviral activity against McIntyre strain of herpes simplex virus-1 in primary rabbit kidney cell cultures1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine.
AID161453Antiviral activity against F strain of herpes simplex virus-1 in primary rabbit kidney cell cultures1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine.
AID161450Minimum cytotoxic concentration required to cause a microscopically detectable alteration of rabbit kidney cell morphology1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine.
AID87829Minimum inhibitory concentration (MIC) required to reduce HSV-2 strain (Lyons) induced cytopathogenicity in primary rabbit kidney cell cultures1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID84064Antiviral activity against herpes simplex virus(1) strain 377, expressed as virus rating. Experiment 21983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
AID87509Minimum inhibitory concentration (MIC) required to reduce HSV-1 strain (F) induced cytopathogenicity in primary rabbit kidney cell cultures1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID217750Antiherpes activity was measured in a plaque reduction assay in Vero cells, against HSV-2 strain 186.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Fluoro carbocyclic nucleosides: synthesis and antiviral activity of 2'- and 6'-fluoro carbocyclic pyrimidine nucleosides including carbocyclic 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyluracil and carbocyclic 1-(2-deoxy-2-fluoro-beta-D-arabinofu
AID161451Antiviral activity against 196 strain of herpes simplex virus-2 in primary rabbit kidney cell cultures1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine.
AID83903Minimum inhibitory concentration (MIC50) in Herpes simplex virus type-1 (HSV-1) using 377 strain. Experiment 11983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
AID161452Antiviral activity against B2006 strain of thymidine kinase deficient (TK-) herpes simplex virus-1 in primary rabbit kidney cell cultures1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine.
AID83904Minimum inhibitory concentration (MIC50) in Herpes simplex virus type-1 (HSV-1) using 377 strain. Experiment 21983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
AID217422Cytotoxic effect on Vero cells was determined in mock infected cell monolayers incubated with the compound for 48 hr at 37 degree celsius.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Fluoro carbocyclic nucleosides: synthesis and antiviral activity of 2'- and 6'-fluoro carbocyclic pyrimidine nucleosides including carbocyclic 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyluracil and carbocyclic 1-(2-deoxy-2-fluoro-beta-D-arabinofu
AID85094Antiviral activity against herpes simplex virus(2) strain MS expressed as virus rating. Experiment 21983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
AID83907Minimum inhibitory concentration (MIC50) in Herpes simplex virus type-1 (HSV-1) using 377 strain. Experiment 41983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
AID87830Minimum inhibitory concentration (MIC) required to reduce HSV-2 strain G induced cytopathogenicity in primary rabbit kidney cell cultures1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID210687Catalytic turnover constant of compound against HSV-1 thymidine kinase; ND denotes not determined2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
Synthesis and biological evaluation of 5-substituted derivatives of the potent antiherpes agent (north)-methanocarbathymine.
AID83906Minimum inhibitory concentration (MIC50) in Herpes simplex virus type-1 (HSV-1) using 377 strain. Experiment 31983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
AID85432Inhibition constant against HSV-1 TK2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
Synthesis and biological evaluation of 5-substituted derivatives of the potent antiherpes agent (north)-methanocarbathymine.
AID161456Antiviral activity against Lyons strain of herpes simplex virus-2 in primary rabbit kidney cell cultures1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine.
AID93929Minimum inhibitory concentration (MIC) required to inhibit proliferation of murine leukemia L1210 (TK-)1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID87511Minimum inhibitory concentration (MIC) required to reduce Herpes simplex virus (HSV-1) KOS strain induced cytopathogenicity in primary rabbit kidney cell cultures1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID161458Antiviral activity against VMW 1837 strain of thymidine kinase deficient (TK-) herpes simplex virus-1 in primary rabbit kidney cell cultures1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine.
AID28488Catalytic rate constant was determined; ND: Not determined2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
Synthesis and biological evaluation of 5-substituted derivatives of the potent antiherpes agent (north)-methanocarbathymine.
AID84066Antiviral activity against herpes simplex virus(1) strain 377, expressed as virus rating. Experiment 41983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
AID146666Minimum inhibitory concentration (MIC) required to inhibit proliferation of Novikoff rat hepatoma1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID84968Minimum inhibitory concentration (MIC50) in Herpes simplex virus type-2 (HSV-2) using MS strain. Experiment 21983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
AID87510Minimum inhibitory concentration (MIC) required to reduce HSV-1 strain McIntyre induced cytopathogenicity in primary rabbit kidney cell cultures1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID216379Minimum inhibitory concentration (MIC) required to reduce vesicular stomatis virus induced cytopathogenicity in primary rabbit kidney cell cultures1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID218134Minimum inhibitory concentration (MIC) required to reduce vaccinia virus induced cytopathogenicity in primary rabbit kidney cell cultures1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID217748Antiherpes activity was measured in a plaque reduction assay in Vero cells, against HSV-1 strain KOS.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Fluoro carbocyclic nucleosides: synthesis and antiviral activity of 2'- and 6'-fluoro carbocyclic pyrimidine nucleosides including carbocyclic 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyluracil and carbocyclic 1-(2-deoxy-2-fluoro-beta-D-arabinofu
AID161460Antiviral activity against Vesicular stomatitis virus in primary rabbit kidney cell cultures1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine.
AID89702Minimum inhibitory concentration (MIC) required to inhibit proliferation of human lymphoblast Raji1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID84065Antiviral activity against herpes simplex virus(1) strain 377, expressed as virus rating. Experiment 31983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Carbocyclic analogues of 5-substituted uracil nucleosides: synthesis and antiviral activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (60.00)18.7374
1990's1 (20.00)18.2507
2000's1 (20.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
thymidine
[no description available]		2.0110pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
floxuridine
Floxuridine: An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection; when administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.. floxuridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.		1.9610nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
idoxuridine
[no description available]		3.0750organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
vidarabine
adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.		1.9610beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic
clevudine
[no description available]		1.9710
(north)-methanocarbathymidine
(north)-methanocarbathymidine: also called NMCT. 1-[(1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)bicyclo[3.1.0]hexan-2-yl]thymine : A carbobicyclic compound that is bicyclo[3.1.0]hexane which is substituted at the 2-pro-S, 4-pro-S and 5-pro-R positions by thymin-1-yl, hydroxy, and hydroxymethyl groups, respectively.		2.0110C-glycosyl pyrimidine;
carbobicyclic compound;
primary alcohol;
pyrimidone;
secondary alcohol
brivudine
brivudine: anti-herpes agent		2.3920
5-(2-iodovinyl)-2'-deoxyuridine
[no description available]		1.9610
acyclovir
Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.		2.01102-aminopurines;
oxopurine		antimetabolite;
antiviral drug
ganciclovir
[no description available]		2.01102-aminopurines;
oxopurine		antiinfective agent;
antiviral drug
ConditionIndicatedRelationship StrengthStudiesTrials
Herpes Simplex Virus Infection
[description not available]		01.9610
Herpes Simplex
A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)		01.9610