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Record Information
Version1.0
Creation Date2014-09-11 05:16:06 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003733
Identification
Common NameFluorouracil
ClassSmall Molecule
DescriptionA pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the thymidylate synthetase conversion of deoxyuridylic acid to thymidylic acid.
Contaminant Sources
  • Clean Air Act Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Antimetabolite
  • Antimetabolite, Antineoplastic
  • Drug
  • Immunosuppressive Agent
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
5-FluoracilChEBI
5-Fluoropyrimidine-2,4-dioneChEBI
5-FUChEBI
FluorouraciloChEBI
FluorouracilumChEBI
5-FluorouracilKegg
AdrucilKegg
CaracKegg
FluoroplexKegg
5-FU medacHMDB
5-Fluorouracil-biosynHMDB
5FUHMDB
Dermatech brand OF fluorouracilHMDB
EfudexHMDB
Fluoro uracile icnHMDB
Fluorouracil gryHMDB
Fluorouracil monopotassium saltHMDB
Neocorp brand OF fluorouracilHMDB
Roche brand OF fluorouracilHMDB
Teva brand OF fluorouracilHMDB
5 FU medacHMDB
5 HU hexalHMDB
5-HU hexalHMDB
Dakota, fluorouracileHMDB
EfudixHMDB
Fluorouracil-gryHMDB
Fluorouracile dakotaHMDB
Haemato brand OF fluorouracilHMDB
Haemato fuHMDB
ICN brand OF fluorouracilHMDB
NeofluorHMDB
5 Fluorouracil biosynHMDB
5-FU lederleHMDB
CSP Brand OF fluorouracilHMDB
Dakota brand OF fluorouracilHMDB
Ferrer brand OF fluorouracilHMDB
Fluoro-uracile icnHMDB
Fluorouracil mononitrateHMDB
Fluorouracil monosodium saltHMDB
Fluorouracil teva brandHMDB
Fluorouracilo ferrer farHMDB
FluracedylHMDB
OnkofluorHMDB
Pharmachemie brand OF fluorouracil monosodium saltHMDB
Biosyn brand OF fluorouracilHMDB
5 FU lederleHMDB
5 FluorouracilHMDB
Allergan brand OF fluorouracilHMDB
Dermik brand OF fluorouracilHMDB
Fluorouracil potassium saltHMDB
FluoruracilHMDB
FlurodexHMDB
Gry brand OF fluorouracilHMDB
Haemato-fuHMDB
Hexal brand OF fluorouracilHMDB
Onkoworks brand OF fluorouracilHMDB
RibofluorHMDB
Riemser brand OF fluorouracilHMDB
Medac brand OF fluorouracilHMDB
Ribosepharm brand OF fluorouracilHMDB
Chemical FormulaC4H3FN2O2
Average Molecular Mass130.077 g/mol
Monoisotopic Mass130.018 g/mol
CAS Registry Number51-21-8
IUPAC Name5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Namefluorouracil
SMILESFC1=CNC(=O)NC1=O
InChI IdentifierInChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChI KeyGHASVSINZRGABV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentHalopyrimidines
Alternative Parents
Substituents
  • Hydroxypyrimidine
  • Halopyrimidine
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Capecitabine PathwayNot AvailableNot Available
Fluorouracil PathwayNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point282-283°C
Boiling PointNot Available
Solubility1.11E+004 mg/L (at 22°C)
Predicted Properties
PropertyValueSource
Water Solubility5.86 g/LALOGPS
logP-0.58ALOGPS
logP-0.66ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.18ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.17 m³·mol⁻¹ChemAxon
Polarizability9.46 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-001i-9600000000-8c2b278c2716f3e6b27cView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9800000000-a3301f9fea9145d07480View in MoNA
GC-MSGC-MS Spectrum - CI-Bsplash10-001i-0900000000-76691bd3cba2765d3687View in MoNA
GC-MSGC-MS Spectrum - CI-Bsplash10-001i-0900000000-d801d8209e9a5aa4830bView in MoNA
GC-MSGC-MS Spectrum - CI-Bsplash10-0002-0900000000-7521695ae4a96b4a5a98View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9800000000-a3301f9fea9145d07480View in MoNA
GC-MSGC-MS Spectrum - CI-Bsplash10-001i-0900000000-76691bd3cba2765d3687View in MoNA
GC-MSGC-MS Spectrum - CI-Bsplash10-001i-0900000000-d801d8209e9a5aa4830bView in MoNA
GC-MSGC-MS Spectrum - CI-Bsplash10-0002-0900000000-7521695ae4a96b4a5a98View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-c639ed1b5365f368b59cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-1a7a70df49a360e1458cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-d89f2d944fe1cac39f55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-50b33770c08680863cf6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-cd5bef421a05073cb1f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-3900000000-ec9c9e1dfc9a16f625a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-df98a4532ca49a0a0436View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-50b33770c08680863cf6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-50b33770c08680863cf6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-df98a4532ca49a0a0436View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-b117f5fa58c8f98b5c15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-9000000000-f3e71a41b6d4417d33fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9200000000-29362607b7c48b82973cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-693d492f316b0c7d5ed5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-1900000000-0c0ee9469bf49688c5d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-1900000000-0cecca0d265e958e19d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03e9-1900000000-46f20f71dbc96630cee7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-1900000000-4330f38956afe6c47636View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-2900000000-f935071622b89177697bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1900000000-3fa9b91447db7dc7ba77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-9800000000-32bf878787078ce9d817View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-3ef559051a5b99c94b29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-4900000000-82764fbca3290816328dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9100000000-2da5eb3c925c027b5022View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1cf432837297c55833a5View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9400000000-b8247c8f5c45b12efaa6View in MoNA
1D NMR1H NMR SpectrumNot Available
Toxicity Profile
Route of Exposure28-100%
Mechanism of ToxicityThe precise mechanism of action has not been fully determined, but the main mechanism of fluorouracil is thought to be the binding of the deoxyribonucleotide of the drug (FdUMP) and the folate cofactor, N5дус10-methylenetetrahydrofolate, to thymidylate synthase (TS) to form a covalently bound ternary complex. This results in the inhibition of the formation of thymidylate from uracil, which leads to the inhibition of DNA and RNA synthesis and cell death. Fluorouracil can also be incorporated into RNA in place of uridine triphosphate (UTP), producing a fraudulent RNA and interfering with RNA processing and protein synthesis.
MetabolismHepatic. The catabolic metabolism of fluorouracil results in degradation products ( e.g., CO2, urea and alpha-fluoro-beta-alanine) which are inactive. Route of Elimination: Seven percent to 20% of the parent drug is excreted unchanged in the urine in 6 hours; of this over 90% is excreted in the first hour. The remaining percentage of the administered dose is metabolized, primarily in the liver. Half Life: 10-20 minutes
Toxicity ValuesLD50=230mg/kg (orally in mice)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (3)
Uses/SourcesFor the topical treatment of multiple actinic or solar keratoses. In the 5% strength it is also useful in the treatment of superficial basal cell carcinomas when conventional methods are impractical, such as with multiple lesions or difficult treatment sites. Fluorouracil injection is indicated in the palliative management of some types of cancer, including colon, esophageal, gastric, rectum, breast, biliary tract, stomach, head and neck, cervical, pancreas, renal cell, and carcinoid.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00544
HMDB IDHMDB0014684
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFluorouracil
Chemspider ID3268
ChEBI ID46345
PubChem Compound ID3385
Kegg Compound IDC07649
YMDB IDNot Available
ECMDB IDM2MDB004605
References
Synthesis Reference

Leroy B. Townsend, Robert A. Earl, Steven J. Manning, “Method of synthesizing 1-(tetrahydro-2-furanyl)-5-fluorouracil.” U.S. Patent US3960864, issued October, 1969.

MSDSLink
General References
1. Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8.
2. Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11356943
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12520460
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14769231
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19023200