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CHEBI:63598 - levofloxacin

ChEBI IDCHEBI:63598
ChEBI Namelevofloxacin
Stars
DefinitionAn optically active form of ofloxacin having (S)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase.
Secondary ChEBI IDCHEBI:6440
Last Modified11 June 2024
DownloadsMolfile
FormulaC18H20FN3O4
Net Charge0
Average Mass361.373
Monoisotopic Mass361.14378
SMILESC[C@H]1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23
InChIInChI=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
InChIKeyGSDSWSVVBLHKDQ-JTQLQIEISA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) blood plasma (BTO:0000118) PubMed (17549677)
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor  A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
antibacterial drug  A drug used to treat or prevent bacterial infections.
DNA synthesis inhibitor  Any substance that inhibits the synthesis of DNA.
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.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
levofloxacin (CHEBI:63598) has role antibacterial drug (CHEBI:36047)
levofloxacin (CHEBI:63598) has role DNA synthesis inhibitor (CHEBI:59517)
levofloxacin (CHEBI:63598) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
levofloxacin (CHEBI:63598) has role topoisomerase IV inhibitor (CHEBI:53559)
levofloxacin (CHEBI:63598) is a 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 (CHEBI:194135)
levofloxacin (CHEBI:63598) is a fluoroquinolone antibiotic (CHEBI:87211)
levofloxacin (CHEBI:63598) is a quinolone antibiotic (CHEBI:86324)
levofloxacin (CHEBI:63598) is conjugate acid of levofloxacin(1−) (CHEBI:231553)
levofloxacin (CHEBI:63598) is enantiomer of dextrofloxacin (CHEBI:46577)
Incoming Relation(s)
ofloxacin (CHEBI:7731) has part levofloxacin (CHEBI:63598)
levofloxacin(1−) (CHEBI:231553) is conjugate base of levofloxacin (CHEBI:63598)
dextrofloxacin (CHEBI:46577) is enantiomer of levofloxacin (CHEBI:63598)
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  Source
levofloxacineChemIDplus
levofloxacinoChemIDplus
levofloxacinumChemIDplus
levofloxacinKEGG DRUG
Synonyms  Source
Ofloxacin S-(-)-formKEGG COMPOUND
(S)-ofloxacinChemIDplus
(-)-OfloxacinChemIDplus
(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 acidChemIDplus
(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 acidChEBI
(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 acidChEBI
Manual XrefsDatabases
C07660KEGG COMPOUND
LevofloxacinWikipedia
D08120KEGG DRUG
HMDB0001929HMDB
DB01137DrugBank
LSM-5270LINCS
1569DrugCentral
1899VSDB
LFXPDBeChem
Registry NumbersSources
Reaxys:5385660Reaxys
CAS:100986-85-4KEGG COMPOUND
CAS:100986-85-4ChemIDplus
Citations