levofloxacin (CHEBI:63598)

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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

Supplier Information

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Formula

C18H20FN3O4

Net Charge

Average Mass

361.373

Monoisotopic Mass

361.14378

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]1COC2=C(N3CCN(C)CC3)C(F)=CC3=C2N1C=C(C(O)=O)C3=O

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	Found in blood plasma (BTO:0000118). See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid ) Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	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. DNA synthesis inhibitor Any substance that inhibits the synthesis of DNA. antibacterial drug A drug used to treat or prevent bacterial infections. 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.

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 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 enantiomer of dextrofloxacin (CHEBI:46577)

Incoming	ofloxacin (CHEBI:7731) has part 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

Synonyms	Sources
(−)-ofloxacin	ChEBI
(-)-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
DR 3355	ChEBI
DR-3355	ChEBI
L-ofloxacin	DrugBank
Ofloxacin S-(-)-form	KEGG COMPOUND
S-(−)-ofloxacin	ChEBI

Last Modified

23 November 2022