CHEBI:5100 - flucytosine

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ChEBI Name flucytosine
ChEBI ID CHEBI:5100
Definition An organofluorine compound that is cytosine that is substituted at position 5 by a fluorine. A prodrug for the antifungal 5-fluorouracil, it is used for the treatment of systemic fungal infections.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C4H4FN3O
Net Charge 0
Average Mass 129.09250
Monoisotopic Mass 129.034
InChI InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
InChIKey XRECTZIEBJDKEO-UHFFFAOYSA-N
SMILES Nc1nc(=O)[nH]cc1F
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via pyrimidine antifungal drug )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via pyrimidine antifungal agent )
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via pyrimidine antifungal drug )
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ChEBI Ontology
Outgoing flucytosine (CHEBI:5100) has functional parent cytosine (CHEBI:16040)
flucytosine (CHEBI:5100) has role prodrug (CHEBI:50266)
flucytosine (CHEBI:5100) is a aminopyrimidine (CHEBI:38338)
flucytosine (CHEBI:5100) is a nucleoside analogue (CHEBI:60783)
flucytosine (CHEBI:5100) is a organofluorine compound (CHEBI:37143)
flucytosine (CHEBI:5100) is a pyrimidine antifungal drug (CHEBI:87205)
flucytosine (CHEBI:5100) is a pyrimidone (CHEBI:38337)
IUPAC Name
4-amino-5-fluoropyrimidin-2(1H)-one
INNs Sources
flucytosina WHO MedNet
flucytosine WHO MedNet
flucytosine WHO MedNet
flucytosinum WHO MedNet
Synonyms Sources
5-FC KEGG DRUG
5-Fluorocystosine ChemIDplus
5-Fluorocytosine ChemIDplus
Ancobon (TN) KEGG DRUG
Brand Name Source
Ancotil ChemIDplus
Manual Xrefs Databases
1188 DrugCentral
1LD PDBeChem
D00323 KEGG DRUG
DB01099 DrugBank
Flucytosine Wikipedia
HMDB0015231 HMDB
LSM-5878 LINCS
US2802005 Patent
US2945038 Patent
US3040026 Patent
View more database links
Registry Numbers Types Sources
2022-85-7 CAS Registry Number ChemIDplus
2022-85-7 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
11519290 PubMed citation Europe PMC
14871609 PubMed citation Europe PMC
18731030 PubMed citation Europe PMC
23576540 PubMed citation Europe PMC
25649231 PubMed citation Europe PMC
26201447 PubMed citation Europe PMC
28166217 PubMed citation Europe PMC
Last Modified
15 June 2017