Page last updated: 2024-09-21

fluorodeoxyuridylate

Description

Fluorodeoxyuridylate: 5-Fluoro-2'-deoxyuridylate. An inhibitor of thymidylate synthetase. Formed from 5-fluorouracil or 5-fluorodeoxyuridine. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID8642
CHEMBL ID886
CHEBI ID2129
SCHEMBL ID6107
MeSH IDM0008627

Synonyms (37)

Synonym
[(2r,3s,5r)-5-(5-fluoro-2,4-dioxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
f-dump
5-fluoro-2'-deoxy-5'-monophosphateuridine
5fdump
UFP ,
5-fluoro-2'-deoxyuridine-5'-monophosphate
C04242
5-fluorodeoxyuridine monophosphate
DB03761 ,
fluorodeoxyuridylate
fdump
5'-uridylic acid, 2'-deoxy-5-fluoro-
134-46-3
chebi:2129 ,
5-fluoro-2-deoxyuridine monophosphate (fdump)
CHEMBL886 ,
[(2r,3s,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
2'-deoxy-5-fluorouridine 5'-(dihydrogen phosphate)
phosphoric acid mono-[5-(5-fluoro-2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester
bdbm50022238
5-fluoro-2''-deoxyuridine-5''-monophosphate
phosphoric acid mono-[(2r,3s,5r)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester
(r)-5-fluoro-1-((4s,5r)-4-hydroxy-5-methylphosphate-tetrahydro-furan-2-yl)-1h-pyrimidine-2,4-dione
unii-7cj707h131
7cj707h131 ,
SCHEMBL6107
DTXSID60158450
fosifloxuridine
uridine, 2'-deoxy-5-fluoro-, 5'-(dihydrogen phosphate)
5-fluoro-2'-deoxyuridine 5'-phosphate
18453-22-0
5-fluoro-dump
5-fluoro-2'-deoxy-ump
Q27105559
PD059482
2 inverted exclamation mark -deoxy-5-fluorouridine 5 inverted exclamation mark -phosphate triethylammonium
F90253

Drug Classes (1)

ClassDescription
pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

fluorodeoxyuridylate is involved in 1 pathway(s), involving a total of 0 unique proteins and 15 unique compounds

PathwayProteinsCompounds
Fluoropyrimidine activity015

Protein Targets (8)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidylate synthase Escherichia coliKi0.01000.00300.06870.1500AID220356
Thymidylate synthaseLacticaseibacillus caseiKi4.97600.01001.65509.3900AID1134942; AID1147592; AID1147594
Thymidylate synthaseHomo sapiens (human)Ki0.01400.00010.34353.0000AID709346
Thymidylate synthaseMus musculus (house mouse)IC50 (µMol)2.51680.00041.322610.0000AID212496; AID212498; AID212499; AID212635
Thymidylate synthaseMus musculus (house mouse)Ki0.02000.00341.73759.3000AID211086; AID211087; AID228251; AID228252
Delta-type opioid receptorRattus norvegicus (Norway rat)Ki0.01400.00000.60689.2330AID1134942
Mu-type opioid receptorRattus norvegicus (Norway rat)Ki0.01400.00000.38458.6000AID1134942
Kappa-type opioid receptorRattus norvegicus (Norway rat)Ki0.01400.00000.18683.9500AID1134942
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidylate synthaseLacticaseibacillus caseiKd0.00500.00000.00500.0100AID1147597; AID1147598
[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 synthaseMus musculus (house mouse)Ki'0.00530.00180.04470.1840AID211088; AID211090; AID228253; AID228254
Thymidylate synthaseMus musculus (house mouse)Ki''0.03130.01400.30181.4600AID211236; AID211238; AID228255; AID228256
Thymidylate kinaseMycobacterium tuberculosis H37RvKm420.00004.50004.50004.5000AID211051; AID211056
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (21)

Processvia Protein(s)Taxonomy
dTMP biosynthetic processThymidylate synthaseHomo sapiens (human)
dTTP biosynthetic processThymidylate synthaseHomo sapiens (human)
circadian rhythmThymidylate synthaseHomo sapiens (human)
response to xenobiotic stimulusThymidylate synthaseHomo sapiens (human)
response to toxic substanceThymidylate synthaseHomo sapiens (human)
negative regulation of translationThymidylate synthaseHomo sapiens (human)
uracil metabolic processThymidylate synthaseHomo sapiens (human)
methylationThymidylate synthaseHomo sapiens (human)
response to progesteroneThymidylate synthaseHomo sapiens (human)
response to vitamin AThymidylate synthaseHomo sapiens (human)
response to cytokineThymidylate synthaseHomo sapiens (human)
tetrahydrofolate interconversionThymidylate synthaseHomo sapiens (human)
response to ethanolThymidylate synthaseHomo sapiens (human)
response to organophosphorusThymidylate synthaseHomo sapiens (human)
developmental growthThymidylate synthaseHomo sapiens (human)
cartilage developmentThymidylate synthaseHomo sapiens (human)
response to glucocorticoidThymidylate synthaseHomo sapiens (human)
response to folic acidThymidylate synthaseHomo sapiens (human)
intestinal epithelial cell maturationThymidylate synthaseHomo sapiens (human)
DNA biosynthetic processThymidylate synthaseHomo sapiens (human)
liver regenerationThymidylate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
mRNA regulatory element binding translation repressor activityThymidylate synthaseHomo sapiens (human)
thymidylate synthase activityThymidylate synthaseHomo sapiens (human)
folic acid bindingThymidylate synthaseHomo sapiens (human)
protein homodimerization activityThymidylate synthaseHomo sapiens (human)
sequence-specific mRNA bindingThymidylate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
nucleusThymidylate synthaseHomo sapiens (human)
cytoplasmThymidylate synthaseHomo sapiens (human)
mitochondrionThymidylate synthaseHomo sapiens (human)
mitochondrial inner membraneThymidylate synthaseHomo sapiens (human)
mitochondrial matrixThymidylate synthaseHomo sapiens (human)
cytosolThymidylate synthaseHomo sapiens (human)
mitochondrionThymidylate synthaseHomo sapiens (human)
cytosolThymidylate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (93)

Assay IDTitleYearJournalArticle
AID165909Cytostatic activity against proliferation of Raji/TK cells (deoxythymidine kinase deficient Raji cells)1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
AID212663Compound was evaluated for the inhibition of L1210 Thymidylate synthase1986Journal 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.
AID18726Apparent rate constant Kon for inactivation of dTMP synthase.1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and biological activity of 5-fluoro-2',3'-dideoxy-3'-fluorouridine and its 5'-phosphate.
AID1304932Drug uptake in Sprague-Dawley rat liver S9 fraction treated with (S)-Isopropyl 2-(((R)-(((2R,3S,5R)-5-(5-fluoro-2,4-dioxo 3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methoxy)((2-methylbenzyl)oxy)phosphoryl)amino)propanoate at 20 ug/mL pre2016Journal of medicinal chemistry, 04-28, Volume: 59, Issue:8
Discovery of an Orally Active and Liver-Targeted Prodrug of 5-Fluoro-2'-Deoxyuridine for the Treatment of Hepatocellular Carcinoma.
AID85714Antiviral activity against Herpes Simplex Virus-1 (McIntyre)1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
AID230651Ki/Km values of L1210/0 dTMP synthase for the compound was determined.1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Synthesis and biological properties of some cyclic phosphotriesters derived from 2'-deoxy-5-fluorouridine.
AID212635Inhibition of cellular thymidylate synthase activity of murine leukemia cell line (L1210) in permeabilised cells.1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2'-deoxyuridine and 1-beta-arabinofuranosylcytosine: evidence of phosphoramidase activity.
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.
AID96658Dose inhibiting L1210/0 murine leukemia cell proliferation by 50% in presence of 5 ug/mL of dThd.1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Synthesis and biological properties of some cyclic phosphotriesters derived from 2'-deoxy-5-fluorouridine.
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.
AID96642Cytostatic activity against proliferation of L1210/0 cells (murine leukemia L1210 cells)1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
AID229760Ratio of ID50 upon addition of dThd to the ID50 upon addition of dUrd against the L1210/0 cell proliferation.1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Synthesis and biological properties of some cyclic phosphotriesters derived from 2'-deoxy-5-fluorouridine.
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.
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.
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.
AID220363Binding of 0.1 mM [14C]5,10-CH2-H4 folate to 2.5 nmol dTMP synthetase from Lactobacillus casei1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Interaction of 5-ethynyl-2'-deoxyuridylate with thymidylate synthetase.
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.
AID211240The time dependent reaction (k2''(1/min)) of compound was measured for inactivation of Ehrlich Carcinoma Thymidylate Synthases1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
2-Thio derivatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: synthesis, interaction with tumor thymidylate synthase, and in vitro antitumor 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.
AID232972Ratio of Concentration of intact versus pearmeabilized of above1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2'-deoxyuridine and 1-beta-arabinofuranosylcytosine: evidence of phosphoramidase activity.
AID211241The time dependent reaction (k2''(1/min)) of compound was measured for inactivation of L1210 Thymidylate Synthases1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
2-Thio derivatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: synthesis, 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.
AID1147598Binding affinity to amethopterin-resistant Lactobacillus casei thymidylate synthetase in presence of cofactor not permitting covalent bond formation1977Journal of medicinal chemistry, Nov, Volume: 20, Issue:11
Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
AID704506Ratio of IC50 for human CEM cells expressing human ENT1 transporter in presence of dipyridamole to IC50 for human CEM cells expressing human ENT1 transporter2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Phosphoramidate ProTides of the anticancer agent FUDR successfully deliver the preformed bioactive monophosphate in cells and confer advantage over the parent nucleoside.
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.
AID216408Antiviral activity against vesicular stomatitis virus1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
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.
AID228255Compound was tested for time-dependent slow-binding inhibition (K) of thymidylate synthase from L1210-P 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.
AID228416Compound was tested for time-dependent 1 (k2) inhibition of thymidylate synthase from L1210-R 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.
AID1147597Binding affinity to amethopterin-resistant Lactobacillus casei thymidylate synthetase in presence of cofactor permitting covalent bond formation1977Journal of medicinal chemistry, Nov, Volume: 20, Issue:11
Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
AID211238The reaction rate(Ki'') of compound was measured for inactivation of L1210 Thymidylate Synthases1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
2-Thio derivatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: synthesis, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID23991Half-life period of [6-3H]3''-FFdUMP from its ternary complex with dTMP synthetase.1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and biological activity of 5-fluoro-2',3'-dideoxy-3'-fluorouridine and its 5'-phosphate.
AID220356Compound was evaluated for the inhibition of dTMP synthetase with respect to dUMP.1981Journal of medicinal chemistry, Oct, Volume: 24, Issue:10
Interaction of 1-(5-phospho-beta-D-arabinofuranosyl)-5-substituted-uracils with thymidylate synthetase: mechanism-based inhibition by 1-(5-phospho-beta-D-arabinosyl)-5-fluorouracil.
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.
AID217995Antiviral activity against vaccinia virus1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
AID228256Compound was tested for time-dependent slow-binding inhibition (K) of thymidylate synthase from L1210-R 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.
AID704505Ratio of IC50 for human CEM cells expressing human ENT1 transporter in presence of NBMPR to IC50 for human CEM cells expressing human ENT1 transporter2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Phosphoramidate ProTides of the anticancer agent FUDR successfully deliver the preformed bioactive monophosphate in cells and confer advantage over the parent nucleoside.
AID96655Dose inhibiting L1210/0 murine leukemia cell proliferation by 50%1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Synthesis and biological properties of some cyclic phosphotriesters derived from 2'-deoxy-5-fluorouridine.
AID96656Dose inhibiting L1210/0 murine leukemia cell proliferation by 50% in presence of 125 ug/mL of dUrd.1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Synthesis and biological properties of some cyclic phosphotriesters derived from 2'-deoxy-5-fluorouridine.
AID228258Compound was tested for time-dependent 1 (k2') inhibition of thymidylate synthase from L1210-R 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.
AID85713Antiviral activity against Herpes Simplex Virus-1 (KOS)1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
AID220371In vitro competitive inhibition of cleavage of substrate dUMP phosphorylase.1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and biological activity of 5-fluoro-2',3'-dideoxy-3'-fluorouridine and its 5'-phosphate.
AID1321552Inhibition of Mycobacterium tuberculosis ThyX at 100 uM preincubated with enzyme followed by [5-3H]dUMP substrate addition measured after 30 mins in presence of 5,10-methylenetetrahydrofolate,NADPH and FAD by liquid scintillation counting2016Journal of medicinal chemistry, 10-13, Volume: 59, Issue:19
Virtual Screening and X-ray Crystallography Identify Non-Substrate Analog Inhibitors of Flavin-Dependent Thymidylate Synthase.
AID704507Ratio of IC50 for ENT1 transporter-deficient human CEM cells to IC50 for human CEM cells expressing human ENT1 transporter after 72 hrs by cell counting2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Phosphoramidate ProTides of the anticancer agent FUDR successfully deliver the preformed bioactive monophosphate in cells and confer advantage over the parent nucleoside.
AID99522In vitro percent inhibition at 10 e-8 M against L5178Y cell growth after 72 hr (replicate flasks inoculated with 10 e5 cells were treated with the nucleotide)1980Journal of medicinal chemistry, Nov, Volume: 23, Issue:11
Synthesis and biological activity of 5-fluoro-2'-deoxyuridine 5'-phosphorodiamidates.
AID704508Cytostatic activity against human CEM cells expressing human ENT1 transporter after 72 hrs by cell counting in presence of NBMPR2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Phosphoramidate ProTides of the anticancer agent FUDR successfully deliver the preformed bioactive monophosphate in cells and confer advantage over the parent nucleoside.
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.
AID211088The reaction rate(Ki') of compound was measured for inactivation of Ehrlich Carcinoma Thymidylate Synthases1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
2-Thio derivatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: synthesis, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID17052Apparent rate constant Koff for inactivation of dTMP synthase.1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and biological activity of 5-fluoro-2',3'-dideoxy-3'-fluorouridine and its 5'-phosphate.
AID96659Dose inhibiting L1210/Br-dUrd murine leukemia cell proliferation by 50%1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Synthesis and biological properties of some cyclic phosphotriesters derived from 2'-deoxy-5-fluorouridine.
AID704510Cytostatic activity against human CEM cells expressing human ENT1 transporter after 72 hrs by cell counting2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Phosphoramidate ProTides of the anticancer agent FUDR successfully deliver the preformed bioactive monophosphate in cells and confer advantage over the parent nucleoside.
AID709346Inhibition of human thymidylate synthase expressed in Escherichia coli incubated for 1 hr by spectrophotometry2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
Inhibitor of ovarian cancer cells growth by virtual screening: a new thiazole derivative targeting human thymidylate synthase.
AID212496Inhibition of cellular thymidylate synthase activity of mouse fibroblast (L929 TK-) in intact cells.1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2'-deoxyuridine and 1-beta-arabinofuranosylcytosine: evidence of phosphoramidase activity.
AID1147594Inhibition of amethopterin-resistant Lactobacillus casei thymidylate synthetase-catalyzed 5-BrdUMP dehalogenation by absorbance analysis in absence 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.
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.
AID229757Ratio of ID50 for L1210/0 cell growth and ID50 for L1210/BdUrd cell growth.1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Synthesis and biological properties of some cyclic phosphotriesters derived from 2'-deoxy-5-fluorouridine.
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.
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.
AID84761Antiviral activity against Herpes Simplex Virus-2(G)1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
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.
AID211245The time dependent reaction (k2'(1/min)) of compound was measured for inactivation of L1210 Thymidylate Synthases1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
2-Thio derivatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: synthesis, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID98737In vitro cytotoxicity of compounds were determined on murine leukemia cell line (L1210).1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2'-deoxyuridine and 1-beta-arabinofuranosylcytosine: evidence of phosphoramidase activity.
AID43713In vitro cytotoxicity of compounds were determined on Inhibition of human leukemia cell line(CCRF-CEM). 1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2'-deoxyuridine and 1-beta-arabinofuranosylcytosine: evidence of phosphoramidase activity.
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.
AID211236The reaction rate(Ki'') of compound was measured for inactivation of Ehrlich Carcinoma Thymidylate Synthases1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
2-Thio derivatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: synthesis, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID96643Cytostatic activity against proliferation of L1210/BdU cells (deoxythymidine kinase deficient L1210 cells)1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
AID233941Ratio 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.
AID228254Compound was tested for time-dependent slow-binding inhibition (K') of thymidylate synthase from L1210-R 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.
AID680603TP_TRANSPORTER: transport into inside-out membrane vesicles in membrane vesicle from MRP8-2-expressing LLC-PK1 cells2003The Journal of biological chemistry, Aug-08, Volume: 278, Issue:32
MRP8, ATP-binding cassette C11 (ABCC11), is a cyclic nucleotide efflux pump and a resistance factor for fluoropyrimidines 2',3'-dideoxycytidine and 9'-(2'-phosphonylmethoxyethyl)adenine.
AID211811Compound was tested for its inhibition against Thymidylate synthase up to concentration of 1 mM; IA means inactive1980Journal of medicinal chemistry, Nov, Volume: 23, Issue:11
Synthesis and biological activity of 5-fluoro-2'-deoxyuridine 5'-phosphorodiamidates.
AID84760Antiviral activity against Herpes Simplex Virus-2(196)1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
AID1123575Inhibition of Lactobacillus casei thymidylate synthetase using dUMP as substrate without pre-incubation with enzyme at 1.2 X 10'-7 M relative to control1979Journal of medicinal chemistry, Jan, Volume: 22, Issue:1
Phosphonate analogue of 2'-deoxy-5-fluorouridylic acid.
AID704509Cytostatic activity against human CEM cells expressing human ENT1 transporter after 72 hrs by cell counting in presence of dipyridamole2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Phosphoramidate ProTides of the anticancer agent FUDR successfully deliver the preformed bioactive monophosphate in cells and confer advantage over the parent nucleoside.
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.
AID211244The time dependent reaction (k2'(1/min)) of compound was measured for inactivation of Ehrlich Carcinoma Thymidylate Synthases1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
2-Thio derivatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: synthesis, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID99399Inhibitory activity against Lactobacillus casei MTX-resistant1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Folate analogues. 26. Syntheses and antifolate activity of 10-substituted derivatives of 5,8-dideazafolic acid and of the poly-gamma-glutamyl metabolites of N10-propargyl-5,8-dideazafolic acid (PDDF).
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.
AID228253Compound was tested for time-dependent slow-binding inhibition (K') of thymidylate synthase from L1210-P 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.
AID704511Cytostatic activity against ENT1 transporter-deficient human CEM cells after 72 hrs by cell counting2011Journal of medicinal chemistry, Oct-27, Volume: 54, Issue:20
Phosphoramidate ProTides of the anticancer agent FUDR successfully deliver the preformed bioactive monophosphate in cells and confer advantage over the parent nucleoside.
AID212499Inhibition of cellular thymidylate synthase activity of murine leukemia cell line (L1210) in intact cells.1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2'-deoxyuridine and 1-beta-arabinofuranosylcytosine: evidence of phosphoramidase activity.
AID228257Compound was tested for time-dependent 1 (k2') inhibition of thymidylate synthase from L1210-P 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.
AID211086Apparent Ki value was measured by competitive inhibition of Thymidylate Synthases from Ehrlich Carcinoma cells of mouse1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
2-Thio derivatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: synthesis, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
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.
AID165908Cytostatic activity against proliferation of Raji/0 cells (human lymphoblast Raji cells)1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
AID211087Apparent Ki value was measured by competitive inhibition of Thymidylate Synthases from L1210 cells of mouse1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
2-Thio derivatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: synthesis, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID84762Antiviral activity against Herpes Simplex Virus-2(Lyons)1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
AID211090The reaction rate(Ki') of compound was measured for inactivation of L1210 Thymidylate Synthases1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
2-Thio derivatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: synthesis, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
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.
AID99823In vitro cytotoxicity of compounds were determined on mouse fibroblast (L929 TK-).1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2'-deoxyuridine and 1-beta-arabinofuranosylcytosine: evidence of phosphoramidase activity.
AID85712Antiviral activity against Herpes Simplex Virus-1 (F)1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.
AID212498Inhibition of cellular thymidylate synthase activity of mouse fibroblast (L929 TK-) in permeabilised cells.1996Journal of medicinal chemistry, Nov-08, Volume: 39, Issue:23
Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2'-deoxyuridine and 1-beta-arabinofuranosylcytosine: evidence of phosphoramidase activity.
AID99514Comparative inhibition of L5178Y cell growth in vitro (concentration required for 50% inhibition)1980Journal of medicinal chemistry, Nov, Volume: 23, Issue:11
Synthesis and biological activity of 5-fluoro-2'-deoxyuridine 5'-phosphorodiamidates.
AID228415Compound was tested for time-dependent 1 (k2) inhibition of thymidylate synthase from L1210-P 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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (334)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990155 (46.41)18.7374
1990's107 (32.04)18.2507
2000's43 (12.87)29.6817
2010's25 (7.49)24.3611
2020's4 (1.20)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 (%)
Trials6 (1.72%)5.53%
Reviews18 (5.17%)6.00%
Case Studies2 (0.57%)4.05%
Observational0 (0.00%)0.25%
Other322 (92.53%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (12)

ArticleYear
Cytotoxicity of new duplex drugs linking 3'-C-ethynylcytidine and 5-fluor-2'-deoxyuridine against human melanoma cells.
International journal of cancer, Nov-01, Volume: 131, Issue: 9
2012
Issues of normal tissue toxicity in patient and animal studies--effect of carbogen breathing in rats after 5-fluorouracil treatment.
Acta oncologica (Stockholm, Sweden), Volume: 40, Issue: 5
2001
Targeted drug delivery to chemoresistant cells: folic acid derivatization of FdUMP[10] enhances cytotoxicity toward 5-FU-resistant human colorectal tumor cells.
The Journal of organic chemistry, Aug-24, Volume: 66, Issue: 17
2001
Reduction of 5-fluorouracil (5-FU) gastrointestinal (GI) toxicity resulting from the protection of thymidylate synthase (TS) in GI tissue by repeated simultaneous administration of potassium oxonate (Oxo) in rats.
Cancer chemotherapy and pharmacology, Volume: 46, Issue: 1
2000
Increased cytotoxicity and decreased in vivo toxicity of FdUMP[10] relative to 5-FU.
Nucleosides & nucleotides, Volume: 18, Issue: 8
1999
Determinants of cytotoxicity with prolonged exposure to fluorouracil in human colon cancer cells.
Oncology research, Volume: 9, Issue: 2
1997
Differentially potentiating effects by dipyridamole on cytotoxicity of 5-fluorouracil against three human maxillary cancer cell lines derived from a single tumor.
Anti-cancer drug design, Volume: 8, Issue: 4
1993
Modulation of 1-beta-D-arabinofuranosylcytosine metabolism and cytotoxicity in L1210 cells by fluoropyrimidine pretreatment.
Cancer research, Volume: 42, Issue: 9
1982
Prediction of 5-fluorouracil cytotoxicity towards the Walker carcinosarcoma using peak integrals of fluoronucleotides measured by MRS in vivo.
British journal of cancer, Volume: 60, Issue: 3
1989
Calcium leucovorin and 5-fluorouridine cytotoxicity.
Journal of the South Carolina Medical Association (1975), Volume: 86, Issue: 5
1990
In vitro enhancement of fluoropyrimidine-induced cytotoxicity by leucovorin in colorectal and gastric carcinoma cell lines but not in non-small-cell lung carcinoma cell lines.
Cancer chemotherapy and pharmacology, Volume: 30, Issue: 6
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Long-term Use (1)

ArticleYear
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (3)

ArticleYear
5-ethyl-2'-deoxyuridine, a modulator of both antitumour action and pharmacokinetics of 5-fluorouracil.
Journal of cancer research and clinical oncology, Volume: 125, Issue: 12
1999
18F-radiopharmacokinetics of [18F]-5-fluorouracil in a mouse bearing two colon tumors with a different 5-fluorouracil sensitivity: a study for a correlation with oncological results.
Nuclear medicine and biology, Volume: 23, Issue: 3
1996
Prediction of 5-fluorouracil cytotoxicity towards the Walker carcinosarcoma using peak integrals of fluoronucleotides measured by MRS in vivo.
British journal of cancer, Volume: 60, Issue: 3
1989
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (1)

ArticleYear
Discovery of an Orally Active and Liver-Targeted Prodrug of 5-Fluoro-2'-Deoxyuridine for the Treatment of Hepatocellular Carcinoma.
Journal of medicinal chemistry, 04-28, Volume: 59, Issue: 8
2016
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (6)

ArticleYear
Two nanoformulations induce reactive oxygen species and immunogenetic cell death for synergistic chemo-immunotherapy eradicating colorectal cancer and hepatocellular carcinoma.
Molecular cancer, 01-06, Volume: 20, Issue: 1
2021
Positive interaction between 5-FU and FdUMP[10] in the inhibition of human colorectal tumor cell proliferation.
Antisense & nucleic acid drug development, Volume: 9, Issue: 5
1999
Synthesis and antitumor evaluation of bis[(pivaloyloxy)methyl] 2'-deoxy-5-fluorouridine 5'-monophosphate (FdUMP): a strategy to introduce nucleotides into cells.
Journal of medicinal chemistry, Nov-11, Volume: 37, Issue: 23
1994
On the mechanism of cytotoxicity of fluorinated pyrimidines in four human colon adenocarcinoma xenografts maintained in immune-deprived mice.
Cancer, Mar-15, Volume: 45, Issue: 5 Suppl
1980
Synthesis and biological evaluation of neutral derivatives of 5-fluoro-2'-deoxyuridine 5'-phosphate.
Journal of medicinal chemistry, Volume: 26, Issue: 8
1983
Selective expansion of 5,10-methylenetetrahydrofolate pools and modulation of 5-fluorouracil antitumor activity by leucovorin in vivo.
Cancer research, May-15, Volume: 49, Issue: 10
1989
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]