CHEBI:100246 - norfloxacin

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ChEBI Name norfloxacin
ChEBI ID CHEBI:100246
Definition A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:7629
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Formula C16H18FN3O3
Net Charge 0
Average Mass 319.33080
Monoisotopic Mass 319.133
InChI InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)
InChIKey OGJPXUAPXNRGGI-UHFFFAOYSA-N
SMILES CCn1cc(C(O)=O)c(=O)c2cc(F)c(cc12)N1CCNCC1
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
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.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via quinolone antibiotic )
(via heterocyclic antibiotic )
(via fluoroquinolone antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
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ChEBI Ontology
Outgoing norfloxacin (CHEBI:100246) has role antibacterial drug (CHEBI:36047)
norfloxacin (CHEBI:100246) has role DNA synthesis inhibitor (CHEBI:59517)
norfloxacin (CHEBI:100246) has role environmental contaminant (CHEBI:78298)
norfloxacin (CHEBI:100246) has role xenobiotic (CHEBI:35703)
norfloxacin (CHEBI:100246) is a N-arylpiperazine (CHEBI:46848)
norfloxacin (CHEBI:100246) is a fluoroquinolone antibiotic (CHEBI:87211)
norfloxacin (CHEBI:100246) is a quinolinemonocarboxylic acid (CHEBI:26512)
norfloxacin (CHEBI:100246) is a quinolone (CHEBI:23765)
norfloxacin (CHEBI:100246) is a quinolone antibiotic (CHEBI:86324)
IUPAC Name
1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
INNs Sources
norfloxacin KEGG DRUG
norfloxacine ChemIDplus
norfloxacino ChemIDplus
norfloxacinum ChemIDplus
Synonyms Sources
1,4-Dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid ChemIDplus
1-Ethyl-6-fluor-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-chinolincarbonsäure ChemIDplus
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid ChemIDplus
NFLX KEGG DRUG
Database Links Databases
1967 DrugCentral
BE863429 Patent
C06687 KEGG COMPOUND
D00210 KEGG DRUG
DB01059 DrugBank
DE2840910 Patent
HMDB0015192 HMDB
LSM-5286 LINCS
Norfloxacin Wikipedia
US4146719 Patent
US4292317 Patent
View more database links
Registry Numbers Types Sources
1576626 Gmelin Registry Number Gmelin
567897 Beilstein Registry Number Beilstein
567897 Reaxys Registry Number Reaxys
70458-96-7 CAS Registry Number KEGG COMPOUND
70458-96-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
3317294 PubMed citation Europe PMC
3908074 PubMed citation Europe PMC
6211142 PubMed citation Europe PMC
6224685 PubMed citation Europe PMC
6234465 PubMed citation Europe PMC
6454381 PubMed citation Europe PMC
6461606 PubMed citation Europe PMC
Last Modified
22 February 2017