Page last updated: 2024-08-02 00:22:02

5-(2-iodovinyl)-2'-deoxyuridine

Description

5-(2-iodovinyl)-2'-deoxyuridine: RN given refers to cpd without isomeric designation [MeSH]

Cross-References

ID SourceID
PubMed CID6440124
PubMed CID6438371
CHEMBL ID223205
SCHEMBL ID1626547
SCHEMBL ID1626550
MeSH IDM0096083

Synonyms (24)

Synonym
1-((2r,4s,5r)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-((e)-2-iodo-vinyl)-1-h-pyrimidine-2,4-dione
(e)-5-(2-iodovinyl)-durd
ivdu
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-[(e)-2-iodovinyl]pyrimidine-2,4-dione
uridine, 2'-deoxy-5-(2-iodoethenyl)-, (e)-
uridine, 2'-deoxy-5-(2-iodovinyl)-, (e)-
brn 0758154
(e)-5-(2-iodovinyl)deoxyuridine
(e)-2'-deoxy-5-(2-iodovinyl)uridine
(e)-5-(2-iodovinyl)-2'-deoxyuridine
CHEMBL223205
unii-4wlk8jc9ar
69304-48-9
e-5-(2-iodovinyl)-2'-deoxyuridine
4wlk8jc9ar ,
SCHEMBL1626547
SCHEMBL1626550
DTXSID70219364
Q27260602
5-(2-iodovinyl)-2'-deoxyuridine
e-5-(2-iodovinyl)-durd
uridine, 2'-deoxy-5-(2-iodoethenyl)-
1-[(4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(z)-2-iodoethenyl]pyrimidine-2,4-dione
87727-68-2

Bioassays (25)

Assay IDTitleYearJournalArticle
AID91297Inhibitory concentration of the drug against the cytopathic effect for E-377 strain of herpes simplex virus-1 (HSV-1) in human HFF cells1993Journal of medicinal chemistry, Aug-20, Volume: 36, Issue:17
ISSN: 0022-2623
Synthesis and antiviral activity of novel 5-(1-azido-2-haloethyl) and 5-(1-azido-, amino-, or methoxyethyl) analogs of 2'-deoxyuridine.
AID91307Concentration of the drug required to reduce the uptake of neural red stain by uninfected cell monolayers (HFF)1993Journal of medicinal chemistry, Aug-20, Volume: 36, Issue:17
ISSN: 0022-2623
Synthesis and antiviral activity of novel 5-(1-azido-2-haloethyl) and 5-(1-azido-, amino-, or methoxyethyl) analogs of 2'-deoxyuridine.
AID91306Concentration of the drug required to reduce the proliferation of human foreskin fibroblast cells1993Journal of medicinal chemistry, Aug-20, Volume: 36, Issue:17
ISSN: 0022-2623
Synthesis and antiviral activity of novel 5-(1-azido-2-haloethyl) and 5-(1-azido-, amino-, or methoxyethyl) analogs of 2'-deoxyuridine.
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
ISSN: 0022-2623
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID146667Minimum inhibitory concentration (MIC) required to inhibit proliferation of Novikoff rat hepatoma1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
ISSN: 0022-2623
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
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
ISSN: 0022-2623
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID216193Dose to inhibit plaque formation in vero cells infected with herpes simplex virus type-1 (HSV-1,strainJLJ) was determined1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
ISSN: 0022-2623
Synthesis and antiviral and cytotoxic activity of iodohydrin and iodomethoxy derivatives of 5-vinyl-2'-deoxyuridines, 2'-fluoro-2'-deoxyuridine, and uridine.
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
ISSN: 0022-2623
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID144640Inhibition constant was determined for the facilitated transport of [3N]-thymidine by murine erythrocyte NBMPR-sensitive nucleoside transporter.1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
ISSN: 0022-2623
Synthesis and antiviral and cytotoxic activity of iodohydrin and iodomethoxy derivatives of 5-vinyl-2'-deoxyuridines, 2'-fluoro-2'-deoxyuridine, and uridine.
AID91295Inhibitory concentration of the drug against the cytopathic effect for AD169 strain of epstein barr virus-2 (HCMV) in human HFF cells1993Journal of medicinal chemistry, Aug-20, Volume: 36, Issue:17
ISSN: 0022-2623
Synthesis and antiviral activity of novel 5-(1-azido-2-haloethyl) and 5-(1-azido-, amino-, or methoxyethyl) analogs of 2'-deoxyuridine.
AID165905Inhibitory concentration of the drug against the antigen production against P3HR-1 strain of epstein barr virus-2 (EBV) in Raji cells; ND is Not Determined1993Journal of medicinal chemistry, Aug-20, Volume: 36, Issue:17
ISSN: 0022-2623
Synthesis and antiviral activity of novel 5-(1-azido-2-haloethyl) and 5-(1-azido-, amino-, or methoxyethyl) analogs of 2'-deoxyuridine.
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
ISSN: 0022-2623
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID93932Minimum inhibitory concentration (MIC) required to inhibit proliferation of murine leukemia L1210 (wild type)1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
ISSN: 0022-2623
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID222316Minimum inhibitory concentration (MIC) required to inhibit proliferation of human lymphoblast Raji1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
ISSN: 0022-2623
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID91301Inhibitory concentration of the drug against the cytopathic effect for ellen strain of varicella zoster virus-2 (VZV-2) in human HFF cells1993Journal of medicinal chemistry, Aug-20, Volume: 36, Issue:17
ISSN: 0022-2623
Synthesis and antiviral activity of novel 5-(1-azido-2-haloethyl) and 5-(1-azido-, amino-, or methoxyethyl) analogs of 2'-deoxyuridine.
AID85249Inhibitory activity against HSV-12003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
ISSN: 0022-2623
Synthesis of 3'- and 5'-nitrooxy pyrimidine nucleoside nitrate esters: "nitric oxide donor" agents for evaluation as anticancer and antiviral agents.
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
ISSN: 0022-2623
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID91299Inhibitory concentration of the drug against the cytopathic effect for MS strain of herpes simplex virus-2 (HSV-2) in human HFF cells1993Journal of medicinal chemistry, Aug-20, Volume: 36, Issue:17
ISSN: 0022-2623
Synthesis and antiviral activity of novel 5-(1-azido-2-haloethyl) and 5-(1-azido-, amino-, or methoxyethyl) analogs of 2'-deoxyuridine.
AID93930Minimum inhibitory concentration (MIC) required to inhibit proliferation of murine leukemia L1210 (TK-)1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
ISSN: 0022-2623
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID280941Cytotoxicity against mouse L1210/0 cells after 48 hrs2007Journal of medicinal chemistry, Apr-05, Volume: 50, Issue:7
ISSN: 0022-2623
Probing the anticancer activity of nucleoside analogues: a QSAR model approach using an internally consistent training set.
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
ISSN: 0022-2623
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
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
ISSN: 0022-2623
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID217835Minimum inhibitory concentration (MIC) required to reduce vaccinia virus induced cytopathogenicity in primary rabbit kidney cell cultures1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
ISSN: 0022-2623
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
AID85250Inhibitory activity against HSV-22003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
ISSN: 0022-2623
Synthesis of 3'- and 5'-nitrooxy pyrimidine nucleoside nitrate esters: "nitric oxide donor" agents for evaluation as anticancer and antiviral agents.
AID229018Inhibitory activity against vaccinia virus2003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
ISSN: 0022-2623
Synthesis of 3'- and 5'-nitrooxy pyrimidine nucleoside nitrate esters: "nitric oxide donor" agents for evaluation as anticancer and antiviral agents.

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-199023 (69.70)18.7374
1990's5 (15.15)18.2507
2000's4 (12.12)29.6817
2010's1 (3.03)24.3611
2020's0 (0.00)2.80

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%
Other34 (100.00%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
fluorouracilnucleobase analogue;
organofluorine compound
antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
1990200725.5low001100
thymidinepyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
2003200321.0low000100
floxuridinenucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside
antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
2003200719.0low000200
idoxuridineorganoiodine compound;
pyrimidine 2'-deoxyribonucleoside
antiviral drug;
DNA synthesis inhibitor
1985200725.7low010200
bromodeoxyuridinepyrimidine 2'-deoxyribonucleosideantimetabolite;
antineoplastic agent
2007200717.0low000100
cytarabinebeta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside
antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
2007200717.0low000100
trifluridinenucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside
antimetabolite;
antineoplastic agent;
antiviral drug;
EC 2.1.1.45 (thymidylate synthase) inhibitor
2007200717.0low000100
isosorbide dinitrateglucitol derivative;
nitrate ester
nitric oxide donor;
vasodilator agent
2003200321.0low000100
deoxyuridinepyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
1990199034.0low001000
adefovir6-aminopurines;
ether;
phosphonic acids
antiviral drug;
DNA synthesis inhibitor;
drug metabolite;
HIV-1 reverse transcriptase inhibitor;
nephrotoxic agent
2007200717.0low000100
9-(2-phosphonylmethoxyethyl)-2,6-diaminopurine2007200717.0low000100
thymine arabinosideN-glycosyl compound2007200717.0low000100
edoxudinpyrimidine 2'-deoxyribonucleoside1993200724.0low001100
n-(2-(hydroxyethoxy)methyl)-5-methyluracil2007200717.0low000100
5-fluoro-1-((2-hydroxyethoxy)methyl)uracil2007200717.0medium000100
5-hydroxymethyl-2'-deoxyuridinepyrimidine 2'-deoxyribonucleoside2007200717.0medium000100
msh release-inhibiting hormoneoligopeptide2007200717.0low000100
5-hydroxy-2'-deoxyuridine2007200717.0medium000100
5-formyl-2'-deoxyuridine2007200717.0low000100
5-nitro-2'-deoxyuridine2007200717.0medium000100
5-vinyl-2'-deoxyuridine2007200717.0low000100
5-propyl-2'-deoxyuridine2007200717.0medium000100
adenosine-5'-carboxaldehydeadenosines2007200717.0high000100
brivudine1990200725.5low001100
carbocyclic 5-iodo-2'-deoxyuridine1985198539.0high010000
melphalanL-phenylalanine derivative;
nitrogen mustard;
non-proteinogenic L-alpha-amino acid;
organochlorine compound
alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent
1990199034.0low001000
5-ethynyl-2'-deoxyuridine2007200717.0low000100
5-cyano-2'-deoxyuridine2007200717.0medium000100
5-(2-chloroethyl)-2'-deoxyuridinepyrimidine 2'-deoxyribonucleoside1990199034.0low001000
acyclovir2-aminopurines;
oxopurine
antimetabolite;
antiviral drug
1990200727.3low002100
ganciclovir2-aminopurines;
oxopurine
antiinfective agent;
antiviral drug
1993199331.0low001000
9-((2-phosphonylmethoxy)ethyl)guaninephosphoethanolamine2007200717.0low000100
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
thymidinepyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
1986198737.5low020000
floxuridinenucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside
antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
1986200429.0low010100
idoxuridineorganoiodine compound;
pyrimidine 2'-deoxyribonucleoside
antiviral drug;
DNA synthesis inhibitor
1981201035.6high0223300
bromodeoxyuridinepyrimidine 2'-deoxyribonucleosideantimetabolite;
antineoplastic agent
1981198739.6medium0110000
fluorodeoxyuridylatepyrimidine 2'-deoxyribonucleoside 5'-monophosphate1981198143.0low010000
cyclopentanecycloalkane;
cyclopentanes;
volatile organic compound
non-polar solvent1990199034.0low001000
deoxyuridinepyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
1981199040.5low031000
brominediatomic bromine1984198440.0low010000
etoposidebeta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound
antineoplastic agent;
DNA synthesis inhibitor
1988198836.0low010000
aminopterindicarboxylic acidEC 1.5.1.3 (dihydrofolate reductase) inhibitor;
mutagen
1986198638.0low010000
brivudine1981198739.8medium0100000
bromodeoxycytidine1985198539.0low010000
1-(3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-(2-iodovinyl)-2,4-(1h,3h)-pyrimidinedione1990199034.0medium001000
5-(1-propenyl)-2'-deoxyuridine1981198143.0medium010000
5-(2-iodovinyl)-1-(2'-fluoro-2'-deoxyuridine)2004200420.0medium000100
i(3)so3-galactosylceramidegalactosylceramide sulfate;
N-acyl-beta-D-galactosylsphingosine
1988198836.0low010000
phosphatidylcholines1,2-diacyl-sn-glycero-3-phosphocholine1988198836.0low010000
acyclovir2-aminopurines;
oxopurine
antimetabolite;
antiviral drug
1985198937.3low030000
ganciclovir2-aminopurines;
oxopurine
antiinfective agent;
antiviral drug
2010201014.0low000100
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Astrocytoma, Grade IV02010201014.0low000100
Benign Neoplasms02004200420.0low000100
Benign Neoplasms, Brain02010201014.0low000100
Brain Inflammation01984198837.3medium060000
Brain Neoplasms02010201014.0low000100
Cancer of Colon02004200420.0low000100
Cell Transformation, Viral01982198639.7low030000
Colonic Neoplasms02004200420.0low000100
Encephalitis01984198837.3medium060000
Experimental Mammary Neoplasms01985199536.2low031000
Furrow Keratitis01985198539.0low010000
Glioblastoma02010201014.0low000100
Herpes Simplex01984198837.7medium070000
Herpes Simplex Virus Infection01984198837.7medium070000
Neoplasms02004200420.0low000100
Cytomegalovirus01993199331.0low001000
Herpes Simplex01985198539.0low010000
Herpes Simplex Virus Infection01985198539.0low010000
Leukemia L 121001990199034.0low001000
Leukemia P38801990199034.0low001000

Pharmacokinetics (1)

ArticleYear
Pharmacokinetics and metabolism of E-5-(2-[131I]iodovinyl)-2'-deoxyuridine in dogs.
Antimicrobial agents and chemotherapy, , Volume: 29, Issue:2
1986