gatifloxacin (CHEBI:5280)

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ChEBI Name	gatifloxacin

ChEBI ID	CHEBI:5280

Definition	A monocarboxylic acid that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted on the nitrogen by a cyclopropyl group and at positions 6, 7, and 8 by fluoro, 3-methylpiperazin-1-yl, and methoxy groups, respectively. Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial topoisomerase type-II enzymes.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:101712

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Formula

C19H22FN3O4

Net Charge

Average Mass

375.39410

Monoisotopic Mass

375.15943

InChI

InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26)

InChIKey

XUBOMFCQGDBHNK-UHFFFAOYSA-N

SMILES

COc1c(N2CCNC(C)C2)c(F)cc2c1n(cc(C(O)=O)c2=O)C1CC1

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):	antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. (via quinolone antibiotic ) (via heterocyclic antibiotic ) 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.

Application(s):	antiinfective agent A substance used in the prophylaxis or therapy of infectious diseases.

ChEBI Ontology
Outgoing	gatifloxacin (CHEBI:5280) has role antiinfective agent (CHEBI:35441) gatifloxacin (CHEBI:5280) has role antimicrobial agent (CHEBI:33281) gatifloxacin (CHEBI:5280) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750) gatifloxacin (CHEBI:5280) is a N-arylpiperazine (CHEBI:46848) gatifloxacin (CHEBI:5280) is a organofluorine compound (CHEBI:37143) gatifloxacin (CHEBI:5280) is a quinolinemonocarboxylic acid (CHEBI:26512) gatifloxacin (CHEBI:5280) is a quinolone (CHEBI:23765) gatifloxacin (CHEBI:5280) is a quinolone antibiotic (CHEBI:86324)

Incoming	(R)-gatifloxacin (CHEBI:53560) is a gatifloxacin (CHEBI:5280) (S)-gatifloxacin (CHEBI:53562) is a gatifloxacin (CHEBI:5280)

IUPAC Name

1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Synonyms	Sources
1-Cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid	ChemIDplus
1-cyclopropyl-6-fluoro- 8-methoxy-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline-3-carboxylic acid	ChEMBL
AM 1155	KEGG COMPOUND

Last Modified

22 February 2017