Compounds > 5-iodo-2'-deoxyuridine 5'-monophosphate
Page last updated: 2024-12-08

5-iodo-2'-deoxyuridine 5'-monophosphate

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Description

iododeoxyuridylate: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID449489
CHEMBL ID1160594
SCHEMBL ID285181
MeSH IDM0157451

Synonyms (17)

Synonym
idump
1-{(4s,2r,5r)-4-hydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-5-iodo-1,3-dihydropyrimidine-2,4-dione
[(2r,3s,5r)-3-hydroxy-5-(5-iodo-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
DB02324
5IU ,
5-iodo-2'-deoxyuridine-5'-monophosphate
iododeoxyuridylate
[(2r,3s,5r)-3-hydroxy-5-(5-iodo-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate
2'-deoxy-5-iodouridine 5'-(dihydrogen phosphate)
1763-02-6
CHEMBL1160594 ,
5-iodo-dump
5-iodo-2'-deoxyuridine 5'-monophosphate
SCHEMBL285181
bdbm50010242
((2r,3s,5r)-3-hydroxy-5-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate
PD060159

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" In conclusion, the bioavailability of 5-iodo 2'-deoxyuridine 5'-monophosphate to the parenchymal liver cell is dramatically enhanced as a result of the conjugation of the anti-viral drugs to lactosylated poly-L-lysine."( Specific targeting of the antiviral drug 5-iodo 2'-deoxyuridine to the parenchymal liver cell using lactosylated poly-L-lysine.
Beuting, DM; Biessen, EA; Bijsterbosch, MK; Van Berkel, TJ; Vietsch, H, 1994)		0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidylate synthaseLacticaseibacillus caseiKi1.60000.01001.65509.3900AID1134942; AID1147592
Thymidylate synthaseMus musculus (house mouse)Ki7.33500.00341.73759.3000AID228251; AID228252
Delta-type opioid receptorRattus norvegicus (Norway rat)Ki1.60000.00000.60689.2330AID1134942
Mu-type opioid receptorRattus norvegicus (Norway rat)Ki1.60000.00000.38458.6000AID1134942
Kappa-type opioid receptorRattus norvegicus (Norway rat)Ki1.60000.00000.18683.9500AID1134942
[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)
Thymidylate synthaseLacticaseibacillus caseiKm1.44001.44004.33505.7000AID1147595
Thymidylate kinaseMycobacterium tuberculosis H37RvKm140.00004.50004.50004.5000AID211051; AID211056
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (25)

Assay IDTitleYearJournalArticle
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.
AID233940Ratio between Ki of L1210-P enzyme and Michaelis-Menten constant (kM)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.
AID1147592Inhibition of amethopterin-resistant Lactobacillus casei thymidylate synthetase-catalyzed dTMP formation using dUMP as substrate by spectrophotometric analysis in presence of CH2-H4-folate1977Journal of medicinal chemistry, Nov, Volume: 20, Issue:11
Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
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.
AID211057Enzyme Kinetic constant was determined in the presence of Mycobacterium tuberculosis thymidine monophosphate kinase2002Bioorganic & medicinal chemistry letters, Oct-07, Volume: 12, Issue:19
Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
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.
AID211054Kinetic parameter Vm of thymidine monophosphate kinase (TMPKmt) in Mycobacterium tuberculosis was determined2003Bioorganic & medicinal chemistry letters, Sep-15, Volume: 13, Issue:18
Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID211051Affinity towards thymidine monophosphate kinase (TMPKmt) in Mycobacterium tuberculosis2003Bioorganic & medicinal chemistry letters, Sep-15, Volume: 13, Issue:18
Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
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.
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.
AID1147596Activity at amethopterin-resistant Lactobacillus casei thymidylate synthetase assessed as rate of dTMP formation by absorbance analysis in presence of CH2-H4-folate1977Journal of medicinal chemistry, Nov, Volume: 20, Issue:11
Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
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.
AID1147595Activity at amethopterin-resistant Lactobacillus casei thymidylate synthetase assessed as dTMP formation by absorbance analysis in presence of CH2-H4-folate1977Journal of medicinal chemistry, Nov, Volume: 20, Issue:11
Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
AID228252Time-independent inhibition of thymidylate synthase from parenteral L1210 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.
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.
AID233942Ratio between Ki of L1210-R enzyme and Michaelis-Menten constant (kM)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.
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.
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.
AID211056Compound was tested for binding affinity against Mycobacterium tuberculosis thymidine monophosphate kinase2002Bioorganic & medicinal chemistry letters, Oct-07, Volume: 12, Issue:19
Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
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.
AID228251Time-independent inhibition of thymidylate synthase from FdUrd-resistant L1210 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.
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.
AID228417Compound was evaluated for the inhibition of L1210 thymidylate synthetase (L1210 dTMP)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.
AID1134942Competitive inhibition of thymidylate synthase purified from methotrexate-resistant Lactobacillus casei using 2'-deoxy[5-3H]uridine 5'-phosphate by radioisotope assay1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
5-Cyano-2'-deoxyuridine 5'-phosphate: a potent competitive inhibitor of thymidylate synthetase.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (30.77)18.7374
1990's3 (23.08)18.2507
2000's6 (46.15)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]

Market Indicators

Research Demand Index: 11.73

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 Index11.73 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.73)

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%
Other13 (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]		2.4120pyrimidine 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.		2.3820nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
idoxuridine
[no description available]		2.940organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
adenosine diphosphate
Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.		1.9910adenosine 5'-phosphate;
purine ribonucleoside 5'-diphosphate		fundamental metabolite;
human metabolite
bromodeoxyuridine
Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.		2.3820pyrimidine 2'-deoxyribonucleosideantimetabolite;
antineoplastic agent
trifluridine
Trifluridine: An antiviral derivative of THYMIDINE used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis due to HERPES SIMPLEX virus. (From Martindale, The Extra Pharmacopoeia, 30th ed, p557). trifluridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-trifluoromethyluracil as the nucleobase. An antiviral drug used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis.		2.3920nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
EC 2.1.1.45 (thymidylate synthase) inhibitor
fluorodeoxyuridylate
Fluorodeoxyuridylate: 5-Fluoro-2'-deoxyuridylate. An inhibitor of thymidylate synthetase. Formed from 5-fluorouracil or 5-fluorodeoxyuridine.		3.5990pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
5-fluorouridine
[no description available]		2.0110organofluorine compound;
uridines		mutagen
thymidine monophosphate
Thymidine Monophosphate: 5-Thymidylic acid. A thymine nucleotide containing one phosphate group esterified to the deoxyribose moiety.. dTMP : The neutral species of thymidine 5'-monophosphate (2'-deoxythymidine 5'-monophosphate).		3.2360thymidine 5'-monophosphatefundamental metabolite
doxifluridine
doxifluridine : A pyrimidine 5'-deoxyribonucleoside that is 5-fluorouridine in which the hydroxy group at the 5' position is replaced by a hydrogen. It is an oral prodrug of the antineoplastic agent 5-fluorouracil. Designed to circumvent the rapid degradation of 5-fluorouracil by dihydropyrimidine dehydrogenase in the gut wall, it is converted into 5-fluorouracil in the presence of pyrimidine nucleoside phosphorylase.		2.0110organofluorine compound;
pyrimidine 5'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
prodrug
alovudine
[no description available]		2.0110pyrimidine 2',3'-dideoxyribonucleoside
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		2.0110azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
thymine arabinoside
thymine arabinoside: selectively inhibits replication of herpes simplex virus		2.0110N-glycosyl compound
2'-deoxyuridylic acid
2'-deoxyuridylic acid: RN given refers to parent cpd		2.940deoxyuridine phosphate;
pyrimidine 2'-deoxyribonucleoside 5'-monophosphate		Escherichia coli metabolite;
metabolite;
mouse metabolite
5'-amino-2',5'-dideoxythymidine
5'-amino-5'-deoxythymidine: RN given refers to parent cpd		2.0110
3'-azido-3'-deoxythymidine 5'phosphate
3'-azido-3'-deoxythymidine 5'phosphate: inhibits thymidylate kinase		2.4220
5-chloro-2'-deoxyuridine
[no description available]		2.3820
edoxudin
[no description available]		2.0110pyrimidine 2'-deoxyribonucleoside
5-hydroxymethyl-2'-deoxyuridine
[no description available]		210pyrimidine 2'-deoxyribonucleoside
bromodeoxyuridylate
bromodeoxyuridylate: RN given refers to parent cpd		3.4880
3'-amino-2',3'-dideoxythymidine
[no description available]		2.0110
5-nitro-2'-deoxyuridine 5'-monophosphate
[no description available]		1.9510
2'-fluorothymidine
[no description available]		2.0110
n-4-hydroxy-2'-deoxycytidylic acid
N-4-hydroxy-2'-deoxycytidylic acid: reversibly binds to thymidylate synthetase		210
3'-amino-3'-deoxythymidine 5'-monophosphate
[no description available]		2.4220
5-trifluoromethyl-2'-deoxyuridylic acid
[no description available]		2.6530
brivudine
brivudine: anti-herpes agent		1.9610
5-(2-bromovinyl)-2'-deoxyuridylate
5-(2-bromovinyl)-2'-deoxyuridylate: RN given refers to cpd without isomeric designation		1.9610
5-chloro-2'-deoxyuridine 5'-triphosphate
[no description available]		2.6630
5,10-methylenetetrahydrofolic acid
5,10-methylenetetrahydrofolic acid: RN refers to parent cpd(L-Glu)-isomer		1.9810benzamides;
methylenetetrahydrofolic acid
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 1210
[description not available]		01.9610
Germinoblastoma
[description not available]		02.0110
Kaposi Sarcoma
[description not available]		02.0110
Lymphoma
A general term for various neoplastic diseases of the lymphoid tissue.		02.0110
Sarcoma, Kaposi
A multicentric, malignant neoplastic vascular proliferation characterized by the development of bluish-red cutaneous nodules, usually on the lower extremities, most often on the toes or feet, and slowly increasing in size and number and spreading to more proximal areas. The tumors have endothelium-lined channels and vascular spaces admixed with variably sized aggregates of spindle-shaped cells, and often remain confined to the skin and subcutaneous tissue, but widespread visceral involvement may occur. Kaposi's sarcoma occurs spontaneously in Jewish and Italian males in Europe and the United States. An aggressive variant in young children is endemic in some areas of Africa. A third form occurs in about 0.04% of kidney transplant patients. There is also a high incidence in AIDS patients. (From Dorland, 27th ed & Holland et al., Cancer Medicine, 3d ed, pp2105-7) HHV-8 is the suspected cause.		02.0110