CHEBI:46345 - 5-fluorouracil

ChEBI IDCHEBI:46345
ChEBI Name5-fluorouracil
Stars
DefinitionA nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.
Secondary ChEBI IDsCHEBI:2054, CHEBI:46343
Last Modified22 February 2017
DownloadsMolfile
FormulaC4H3FN2O2
Net Charge0
Average Mass130.078
Monoisotopic Mass130.01786
SMILESO=c1ncc(F)c(=O)n1
InChIInChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChIKeyGHASVSINZRGABV-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
environmental contaminant  Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Roles:
xenobiotic  A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
antimetabolite  A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
radiosensitizing agent  A drug that makes increases the sensitivity of tumour cells to radiation therapy.
ChEBI Ontology
Outgoing Relation(s)
5-fluorouracil (CHEBI:46345) has functional parent uracil (CHEBI:17568)
5-fluorouracil (CHEBI:46345) has role antimetabolite (CHEBI:35221)
5-fluorouracil (CHEBI:46345) has role antineoplastic agent (CHEBI:35610)
5-fluorouracil (CHEBI:46345) has role environmental contaminant (CHEBI:78298)
5-fluorouracil (CHEBI:46345) has role immunosuppressive agent (CHEBI:35705)
5-fluorouracil (CHEBI:46345) has role radiosensitizing agent (CHEBI:132992)
5-fluorouracil (CHEBI:46345) has role xenobiotic (CHEBI:35703)
5-fluorouracil (CHEBI:46345) is a nucleobase analogue (CHEBI:67142)
5-fluorouracil (CHEBI:46345) is a organofluorine compound (CHEBI:37143)
IUPAC Names 
5-fluoropyrimidine-2,4(1H,3H)-dione
5-fluorouracil
INNs  Source
fluorouracilWHO MedNet
fluorouracilumChemIDplus
fluorouraciloChemIDplus
fluorouracilChemIDplus
Synonyms  Source
5-FUKEGG COMPOUND
FluorouracilKEGG COMPOUND
5-FluorouracilKEGG COMPOUND
5-Fluoropyrimidine-2,4-dioneChemIDplus
5-FluoracilChemIDplus
Manual XrefsDatabases
C07649KEGG COMPOUND
URFPDBeChem
FluorouracilWikipedia
DB00544DrugBank
D00584KEGG DRUG
HMDB0014684HMDB
LSM-4261LINCS
26DrugCentral
Registry NumbersSources
Beilstein:127172Beilstein
Reaxys:127172Reaxys
CAS:51-21-8KEGG COMPOUND
CAS:51-21-8ChemIDplus
Citations