CHEBI:71415 - nitrofurantoin

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ChEBI Name nitrofurantoin
ChEBI ID CHEBI:71415
Definition An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:7591
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Formula C8H6N4O5
Net Charge 0
Average Mass 238.157
Monoisotopic Mass 238.034
InChI InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+
InChIKey NXFQHRVNIOXGAQ-YCRREMRBSA-N
SMILES C1(N(/N=C/C=2OC(=CC2)[N+]([O-])=O)CC(N1)=O)=O
Roles Classification
Biological Role(s): hepatotoxic agent
A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.
antibacterial drug
A drug used to treat or prevent bacterial infections.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
(via nitrofuran antibiotic )
Application(s): antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
antibacterial drug
A drug used to treat or prevent bacterial infections.
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ChEBI Ontology
Outgoing nitrofurantoin (CHEBI:71415) has functional parent semicarbazide (CHEBI:28306)
nitrofurantoin (CHEBI:71415) has role antibacterial drug (CHEBI:36047)
nitrofurantoin (CHEBI:71415) has role antiinfective agent (CHEBI:35441)
nitrofurantoin (CHEBI:71415) has role hepatotoxic agent (CHEBI:50908)
nitrofurantoin (CHEBI:71415) is a imidazolidine-2,4-dione (CHEBI:24628)
nitrofurantoin (CHEBI:71415) is a nitrofuran antibiotic (CHEBI:87230)
nitrofurantoin (CHEBI:71415) is a organonitrogen heterocyclic antibiotic (CHEBI:25558)
nitrofurantoin (CHEBI:71415) is a organooxygen heterocyclic antibiotic (CHEBI:25807)
IUPAC Name
1-{[(5-nitro-2-furyl)methylene]amino}imidazolidine-2,4-dione
INNs Sources
nitrofurantoin KEGG DRUG
nitrofurantoina ChemIDplus
nitrofurantoine ChemIDplus
nitrofurantoinum ChemIDplus
Synonyms Sources
1-((5-Nitrofurfurylidene)amino)hydantoin ChemIDplus
1-(5-Nitro-2-furfurylidenamino)hydantoin ChemIDplus
1-(5-Nitro-2-furfurylideneamino)hydantoin ChemIDplus
1-[(5-Nitrofurfurylidene)amino]hydantoin NIST Chemistry WebBook
5-Nitrofurantoin NIST Chemistry WebBook
N-(5-Nitrofurfurylidene)-1-aminohydantoin ChemIDplus
Manual Xrefs Databases
1949 DrugCentral
C07268 KEGG COMPOUND
D00439 KEGG DRUG
DB00698 DrugBank
Nitrofurantoin Wikipedia
US2610181 Patent
US2898335 Patent
US2927110 Patent
WO2006019844 Patent
WO2008103673 Patent
WO2010065110 Patent
View more database links
Registry Numbers Types Sources
67-20-9 CAS Registry Number KEGG COMPOUND
67-20-9 CAS Registry Number ChemIDplus
67-20-9 CAS Registry Number NIST Chemistry WebBook
8132135 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017