CHEBI:63598 - levofloxacin

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ChEBI Name levofloxacin
ChEBI ID CHEBI:63598
Definition An optically active form of ofloxacin having (S)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:6440
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Formula C18H20FN3O4
Net Charge 0
Average Mass 361.36750
Monoisotopic Mass 361.144
InChI InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)/t10-/m0/s1
InChIKey GSDSWSVVBLHKDQ-JTQLQIEISA-N
SMILES C[C@H]1COc2c(N3CCN(C)CC3)c(F)cc3c2n1cc(C(O)=O)c3=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
(via ofloxacin )
antibacterial drug
A drug used to treat or prevent bacterial infections.
(via ofloxacin )
topoisomerase IV inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase IV, which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
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.
(via ofloxacin )
antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
(via ofloxacin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing levofloxacin (CHEBI:63598) has role antibacterial drug (CHEBI:36047)
levofloxacin (CHEBI:63598) has role DNA synthesis inhibitor (CHEBI:59517)
levofloxacin (CHEBI:63598) has role topoisomerase IV inhibitor (CHEBI:53559)
levofloxacin (CHEBI:63598) is a fluoroquinolone antibiotic (CHEBI:87211)
levofloxacin (CHEBI:63598) is a ofloxacin (CHEBI:7731)
levofloxacin (CHEBI:63598) is a quinolone antibiotic (CHEBI:86324)
IUPAC Name
(3S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid
INNs Sources
levofloxacin KEGG DRUG
levofloxacine ChemIDplus
levofloxacino ChemIDplus
levofloxacinum ChemIDplus
Synonyms Sources
(-)-Ofloxacin ChemIDplus
(3S)-(-)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid ChEBI
(S)-(-)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzooxazine-6-carboxylic acid ChEBI
(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid ChemIDplus
(S)-Ofloxacin ChemIDplus
L-Ofloxacin DrugBank
Ofloxacin S-(-)-form KEGG COMPOUND
Manual Xrefs Databases
1569 DrugCentral
1899 VSDB
C07660 KEGG COMPOUND
D08120 KEGG DRUG
DB01137 DrugBank
HMDB0001929 HMDB
Levofloxacin Wikipedia
LSM-5270 LINCS
View more database links
Registry Numbers Types Sources
100986-85-4 CAS Registry Number ChemIDplus
5385660 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
21075586 PubMed citation Europe PMC
21965436 PubMed citation Europe PMC
21974858 PubMed citation Europe PMC
22088660 PubMed citation Europe PMC
22221614 PubMed citation Europe PMC
Last Modified
22 February 2017