Floxuridine (CED0005658)

Record Information
Version1.0
Creation Date2016-05-22 03:41:13 UTC
Update Date2026-05-14 16:25:24 UTC
Accession NumberCHEM016712
Identification
Common NameFloxuridine
ClassSmall Molecule
Description
Floxuridine is an organic compound with the chemical formula C9H11FN2O5 and an average molecular weight of 246.19 g/mol. Floxuridine belongs to the pyrimidine 2'-deoxyribonucleosides, a subclass of pyrimidine nucleosides within the organic compounds. Within the biological system, it acts on two recorded protein targets, serving as an inhibitor of Thymidylate synthase (TYMS) and targeting Thymidylate synthase (TMP1). The compound is documented in seven recorded sources. In the realm of healthcare, pharmaceuticals, and veterinary products, it is used as an antineoplastic agent. Other recorded sources include food, food processing, and cookware, specifically regarding food preservation and fermentation processes for beer. It is also associated with household cleaning and consumer products, such as tobacco smoke filters and perfumes within detergents and soaps. Additionally, it is found in electrical and electronic equipment, specifically electrically stimulated smoking devices and conductive bodies characterized by conductive materials. The recorded route of exposure for this compound is intra-arterial.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracilChEBI
1-beta-D-2'-Deoxyribofuranosyl-5-flurouracilChEBI
1beta-D-2'-Deoxyribofuranosyl-5-flurouracilChEBI
2'-Deoxy-5-fluorouridineChEBI
5-Fluoro-2'-deoxyuridineChEBI
5-Fluoro-2-desoxyuridineChEBI
5-FluorodeoxyuridineChEBI
5-Fluorouracil 2'-deoxyribosideChEBI
5-Fluorouracil deoxyribosideChEBI
5FDUChEBI
beta-5-Fluoro-2'-deoxyuridineChEBI
DeoxyfluorouridineChEBI
FdUChEBI
FloxiridinaChEBI
FloxuridinChEBI
FloxuridinumChEBI
FluorodeoxyuridineChEBI
Fluoruridine deoxyriboseChEBI
FUDRKegg
1-(2-Deoxy-b-D-ribofuranosyl)-5-fluorouracilGenerator
1-(2-Deoxy-β-D-ribofuranosyl)-5-fluorouracilGenerator
1-b-D-2'-Deoxyribofuranosyl-5-flurouracilGenerator
1-Β-D-2'-deoxyribofuranosyl-5-flurouracilGenerator
1b-D-2'-Deoxyribofuranosyl-5-flurouracilGenerator
1Β-D-2'-deoxyribofuranosyl-5-flurouracilGenerator
b-5-Fluoro-2'-deoxyuridineGenerator
Β-5-fluoro-2'-deoxyuridineGenerator
5 FluorodeoxyuridineHMDB
FDURHMDB
FDURDHMDB
5-FUdRHMDB
Chemical FormulaC9H11FN2O5
Average Molecular Mass246.192 g/mol
Monoisotopic Mass246.065 g/mol
CAS Registry Number50-91-9
IUPAC Name5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Namefloxuridine
SMILESOC[C@H]1O[C@H](C[C@@H]1O)N1C=C(F)C(=O)NC1=O
InChI IdentifierInChI=1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
InChI KeyODKNJVUHOIMIIZ-RRKCRQDMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassPyrimidine 2'-deoxyribonucleosides
Direct ParentPyrimidine 2'-deoxyribonucleosides
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside
  • Halopyrimidine
  • Hydroxypyrimidine
  • Pyrimidone
  • Aryl fluoride
  • Aryl halide
  • Hydropyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility40.8 g/LALOGPS
logP-1.2ALOGPS
logP-1.3ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)7.68ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.1 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.26 m³·mol⁻¹ChemAxon
Polarizability20.78 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-00lr-9600000000-155a97133c7827d2a1ceNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-001i-3900000000-44f00976f508bab47f36Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00kb-2910000000-2efae68e874a5fdba01cNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00lr-9600000000-155a97133c7827d2a1ceNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-001i-3900000000-44f00976f508bab47f36Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00kb-2910000000-2efae68e874a5fdba01cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0036-9340000000-625fd93cccce9bbf8234Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0gk9-8926000000-e5bea4ee2a8fa95520d5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-e75f17c5e6c58cb63cc4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1900000000-ab9d2ecf3f514e6cd7fdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01q9-7900000000-5b44e036090ffa5616c4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ikd-5890000000-537ea470ce67d29de875Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-2930000000-9edc79b79e109479fd9bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9200000000-8d9d5de0ec79de7d99fdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002b-0290000000-39ab94dde23863db307aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-054o-5920000000-270199a759ef06b114d5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9300000000-4e1f643aecd55a3c5e1aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000t-0590000000-8342a1e97df40065538fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-6910000000-971c4cc98bc9ce3fbe7bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-053r-3900000000-9ea95daa1bfdf562eb70Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2554.0Log mg/kg[1400:4500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
4 pathways
Fluorouracil Metabolism
Fluorouracil Metabolism
Fluorouracil Pyrimidine Analog Action Pathway
Fluorouracil Pyrimidine Analog Action Pathway
Capecitabine Action Pathway (New)
Capecitabine Action Pathway (New)
Floxuridine Drug Metabolism Action Pathway
Floxuridine Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureThymidylate synthaseP07607Mus musculusPredicted (SEA)2.49118
Thymidylate synthase structureClick to view 3D structureThymidylate synthaseP00469Lactobacillus caseiPredicted (SEA)3.11397
Thymidylate kinase structureClick to view 3D structureThymidylate kinaseP9WKE1Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)0.389246
Click to view 3D structureThymidine kinase 2D3ZGQ2Rattus norvegicusPredicted (SEA)0.622794
Click to view 3D structureThymidine kinase, cytosolicP27158Rattus norvegicusPredicted (SEA)0.934191
Click to view 3D structureThymidylate synthaseQ2TA32Bos taurusPredicted (SEA)0.622794
Reverse transcriptase/RNaseH structureClick to view 3D structureReverse transcriptase/RNaseHQ72547Human immunodeficiency virus 1Predicted (SEA)11.1324
Click to view 3D structureThymidine kinaseQ9QNF7HHV-1Predicted (SEA)0.0778492
Click to view 3D structureThymidine kinaseP09250HHV-3Predicted (SEA)0.311397
DNA polymerase delta catalytic subunit structureClick to view 3D structureDNA polymerase delta catalytic subunitP28340HumansPredicted (SEA)2.33548
Thymidylate synthase structureClick to view 3D structureThymidylate synthaseP04818HumansPredicted (SEA)10.5875
Click to view 3D structureThymidine kinase 2, mitochondrialO00142HumansPredicted (SEA)0.934191
Click to view 3D structureRibonuclease pancreaticP61823Bos taurusPredicted (SEA)3.81461
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)52.7818
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)209.414
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)178.275
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)101.282
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)150.015
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)77.8492
Ribonuclease pancreatic structureClick to view 3D structureRibonuclease pancreaticP07998HumansPredicted (SEA)13.6236
Click to view 3D structureThymidylate synthase ThyAP9WFR9Mycobacterium tuberculosisPredicted (SEA)0.0778492
Thymidine kinase, cytosolic structureClick to view 3D structureThymidine kinase, cytosolicP04183HumansPredicted (SEA)0.0778492
Click to view 3D structureThymidine kinaseA3RLP8Macacine herpesvirus 1Predicted (SEA)0.0778492
Click to view 3D structureThymidine kinaseP06479Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1)Predicted (SEA)0.0778492
Click to view 3D structureFlavin-dependent thymidylate synthaseP9WG57Mycobacterium tuberculosisPredicted (SEA)0.155698
Concentrations
Not Available
External Links
DrugBank IDDB00322
HMDB IDHMDB0014467
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFloxuridine
Chemspider ID5586
ChEBI ID60761
PubChem Compound ID5790
Kegg Compound IDC11736
YMDB IDNot Available
ECMDB IDM2MDB004436
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12520460
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19744858
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19917528
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20218622
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20363130
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20391188
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=29438107
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=3950402