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

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

Description

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

Cross-References

ID Source	ID
PubMed CID	449489
CHEMBL ID	1160594
SCHEMBL ID	285181
MeSH ID	M0157451

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

Excerpt	Reference	Relevance
" 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

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Thymidylate synthase	Lacticaseibacillus casei	Ki	1.6000	0.0100	1.6550	9.3900	AID1134942; AID1147592
Thymidylate synthase	Mus musculus (house mouse)	Ki	7.3350	0.0034	1.7375	9.3000	AID228251; AID228252
Delta-type opioid receptor	Rattus norvegicus (Norway rat)	Ki	1.6000	0.0000	0.6068	9.2330	AID1134942
Mu-type opioid receptor	Rattus norvegicus (Norway rat)	Ki	1.6000	0.0000	0.3845	8.6000	AID1134942
Kappa-type opioid receptor	Rattus norvegicus (Norway rat)	Ki	1.6000	0.0000	0.1868	3.9500	AID1134942
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Thymidylate synthase	Lacticaseibacillus casei	Km	1.4400	1.4400	4.3350	5.7000	AID1147595
Thymidylate kinase	Mycobacterium tuberculosis H37Rv	Km	140.0000	4.5000	4.5000	4.5000	AID211051; AID211056
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (25)

Assay ID	Title	Year	Journal	Article
AID87827	Evaluation of antiviral activity against Herpes simplex virus type 2 (HSV-2) strain G	1986	Journal 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.
AID233940	Ratio between Ki of L1210-P enzyme and Michaelis-Menten constant (kM)	2000	Journal 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.
AID1147592	Inhibition of amethopterin-resistant Lactobacillus casei thymidylate synthetase-catalyzed dTMP formation using dUMP as substrate by spectrophotometric analysis in presence of CH2-H4-folate	1977	Journal of medicinal chemistry, Nov, Volume: 20, Issue:11	Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
AID216539	Evaluation of antiviral activity against Vesicular stomatitis virus.	1986	Journal 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.
AID211057	Enzyme Kinetic constant was determined in the presence of Mycobacterium tuberculosis thymidine monophosphate kinase	2002	Bioorganic & 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.
AID220992	Evaluation of antitumor activity against thymidine kinase deficient Raji cell line	1986	Journal 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.
AID211054	Kinetic parameter Vm of thymidine monophosphate kinase (TMPKmt) in Mycobacterium tuberculosis was determined	2003	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 13, Issue:18	Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID211051	Affinity towards thymidine monophosphate kinase (TMPKmt) in Mycobacterium tuberculosis	2003	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 13, Issue:18	Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID98532	Evaluation of cytostatic activity by using antitumor assays against murine leukemia L1210 cells	1986	Journal 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.
AID87507	Evaluation of antiviral activity against Herpes simplex virus type 1 (HSV-1) strain KOS.	1986	Journal 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.
AID1147596	Activity at amethopterin-resistant Lactobacillus casei thymidylate synthetase assessed as rate of dTMP formation by absorbance analysis in presence of CH2-H4-folate	1977	Journal of medicinal chemistry, Nov, Volume: 20, Issue:11	Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
AID98529	Evaluation of antitumor activity against mutant murine leukemia L1210 cells	1986	Journal 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.
AID1147595	Activity at amethopterin-resistant Lactobacillus casei thymidylate synthetase assessed as dTMP formation by absorbance analysis in presence of CH2-H4-folate	1977	Journal of medicinal chemistry, Nov, Volume: 20, Issue:11	Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
AID228252	Time-independent inhibition of thymidylate synthase from parenteral L1210 cells	2000	Journal 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.
AID218132	Evaluation of antiviral activity against Vaccinia virus	1986	Journal 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.
AID233942	Ratio between Ki of L1210-R enzyme and Michaelis-Menten constant (kM)	2000	Journal 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.
AID87508	Evaluation of antiviral activity against Herpes simplex virus type 1 (HSV-1) strain McIntyre	1986	Journal 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.
AID87506	Evaluation of antiviral activity against Herpes simplex virus type 1 (HSV-1) strain F	1986	Journal 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.
AID211056	Compound was tested for binding affinity against Mycobacterium tuberculosis thymidine monophosphate kinase	2002	Bioorganic & 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.
AID87826	Evaluation of antiviral activity against Herpes simplex virus type 2 (HSV-2) strain 196.	1986	Journal 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.
AID228251	Time-independent inhibition of thymidylate synthase from FdUrd-resistant L1210 cells	2000	Journal 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.
AID221339	Evaluation for antitumor activity against human lymphoblast Raji cells	1986	Journal 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.
AID228417	Compound was evaluated for the inhibition of L1210 thymidylate synthetase (L1210 dTMP)	1986	Journal 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.
AID1134942	Competitive inhibition of thymidylate synthase purified from methotrexate-resistant Lactobacillus casei using 2'-deoxy[5-3H]uridine 5'-phosphate by radioisotope assay	1979	Journal of medicinal chemistry, Sep, Volume: 22, Issue:9	5-Cyano-2'-deoxyuridine 5'-phosphate: a potent competitive inhibitor of thymidylate synthetase.
AID87828	Evaluation of antiviral activity against Herpes simplex virus type 2 (HSV-2) strain Lyons	1986	Journal 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)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	4 (30.77)	18.7374
1990's	3 (23.08)	18.2507
2000's	6 (46.15)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (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.

Metric	This Compound (vs All)
Research Demand Index	11.73 (24.57)
Research Supply Index	2.64 (2.92)
Research Growth Index	4.37 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (11.73)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	13 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
thymidine [no description available]	2.41	2	pyrimidine 2'-deoxyribonucleoside	Escherichia 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.	2.38	2	nucleoside analogue; organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; radiosensitizing agent
idoxuridine [no description available]	2.9	4	organoiodine 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.	1.99	1	adenosine 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.	2.38	2	pyrimidine 2'-deoxyribonucleoside	antimetabolite; 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.	2.39	2	nucleoside 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.	3.59	9	pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
5-fluorouridine [no description available]	2.01	1	organofluorine 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).	3.23	6	thymidine 5'-monophosphate	fundamental 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.	2.01	1	organofluorine compound; pyrimidine 5'-deoxyribonucleoside	antimetabolite; antineoplastic agent; prodrug
alovudine [no description available]	2.01	1	pyrimidine 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.	2.01	1	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
thymine arabinoside thymine arabinoside: selectively inhibits replication of herpes simplex virus	2.01	1	N-glycosyl compound
2'-deoxyuridylic acid 2'-deoxyuridylic acid: RN given refers to parent cpd	2.9	4	deoxyuridine 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	2.01	1
3'-azido-3'-deoxythymidine 5'phosphate 3'-azido-3'-deoxythymidine 5'phosphate: inhibits thymidylate kinase	2.42	2
5-chloro-2'-deoxyuridine [no description available]	2.38	2
edoxudin [no description available]	2.01	1	pyrimidine 2'-deoxyribonucleoside
5-hydroxymethyl-2'-deoxyuridine [no description available]	2	1	pyrimidine 2'-deoxyribonucleoside
bromodeoxyuridylate bromodeoxyuridylate: RN given refers to parent cpd	3.48	8
3'-amino-2',3'-dideoxythymidine [no description available]	2.01	1
5-nitro-2'-deoxyuridine 5'-monophosphate [no description available]	1.95	1
2'-fluorothymidine [no description available]	2.01	1
n-4-hydroxy-2'-deoxycytidylic acid N-4-hydroxy-2'-deoxycytidylic acid: reversibly binds to thymidylate synthetase	2	1
3'-amino-3'-deoxythymidine 5'-monophosphate [no description available]	2.42	2
5-trifluoromethyl-2'-deoxyuridylic acid [no description available]	2.65	3
brivudine brivudine: anti-herpes agent	1.96	1
5-(2-bromovinyl)-2'-deoxyuridylate 5-(2-bromovinyl)-2'-deoxyuridylate: RN given refers to cpd without isomeric designation	1.96	1
5-chloro-2'-deoxyuridine 5'-triphosphate [no description available]	2.66	3
5,10-methylenetetrahydrofolic acid 5,10-methylenetetrahydrofolic acid: RN refers to parent cpd(L-Glu)-isomer	1.98	1	benzamides; methylenetetrahydrofolic acid

Condition	Relationship Strength	Studies
Leukemia L 1210 [description not available]	1.96	1
Germinoblastoma [description not available]	2.01	1
Kaposi Sarcoma [description not available]	2.01	1
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	2.01	1
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.	2.01	1

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