CHEBI:46345 - 5-fluorouracil

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ChEBI Name 5-fluorouracil
ChEBI ID CHEBI:46345
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:46343, CHEBI:2054
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Formula C4H3FN2O2
Net Charge 0
Average Mass 130.07730
Monoisotopic Mass 130.01786
InChI InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChIKey GHASVSINZRGABV-UHFFFAOYSA-N
SMILES Fc1c[nH]c(=O)[nH]c1=O
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): 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.
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.
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.
Application(s): radiosensitizing agent
A drug that makes increases the sensitivity of tumour cells to radiation therapy.
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.
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ChEBI Ontology
Outgoing 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 Sources
fluorouracil ChemIDplus
fluorouracil WHO MedNet
fluorouracilo ChemIDplus
fluorouracilum ChemIDplus
Synonyms Sources
5-Fluoracil ChemIDplus
5-Fluoropyrimidine-2,4-dione ChemIDplus
5-Fluorouracil KEGG COMPOUND
5-FU KEGG COMPOUND
Fluorouracil KEGG COMPOUND
Manual Xrefs Databases
26 DrugCentral
C07649 KEGG COMPOUND
D00584 KEGG DRUG
DB00544 DrugBank
Fluorouracil Wikipedia
HMDB0014684 HMDB
LSM-4261 LINCS
URF PDBeChem
View more database links
Registry Numbers Types Sources
127172 Beilstein Registry Number Beilstein
127172 Reaxys Registry Number Reaxys
51-21-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11356943 PubMed citation Europe PMC
12520460 PubMed citation Europe PMC
14769231 PubMed citation Europe PMC
19023200 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comments
2014-05-06 It is found in the blood and urine samples of individuals who have taken this drug.
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag