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5-fluorouracil (CHEBI:46345)

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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:2054, CHEBI:46343
Supplier Information
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Formula Source
C4H3FN2O2 KEGG COMPOUND
Net Charge 0
Average Mass 130.07730
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
Biological Role(s): 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): 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 immunosuppressive agent (CHEBI:35705)
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
Database Links Databases
C07649 KEGG COMPOUND
D00584 KEGG DRUG
DB00544 DrugBank
Fluorouracil Wikipedia
HMDB14684 HMDB
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 CiteXplore
14769231 PubMed citation CiteXplore
19023200 PubMed citation CiteXplore
General Comment
2014-05-06 It is found in the blood and urine samples of individuals who have taken this drug.
 
Last Modified
06 May 2014

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