CHEBI:5280 - gatifloxacin

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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 0
Average Mass 375.39410
Monoisotopic Mass 375.159
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.
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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
INNs Sources
gatifloxacin KEGG DRUG
gatifloxacine WHO MedNet
gatifloxacino WHO MedNet
gatifloxacinum WHO MedNet
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
Manual Xrefs Databases
1280 DrugCentral
C07661 KEGG COMPOUND
D08011 KEGG DRUG
DB01044 DrugBank
EP230295 Patent
Gatifloxacin Wikipedia
LSM-5139 LINCS
US4980470 Patent
View more database links
Registry Numbers Types Sources
112811-59-3 CAS Registry Number DrugBank
112811-59-3 CAS Registry Number ChemIDplus
2281206 Gmelin Registry Number Gmelin
7445861 Reaxys Registry Number Reaxys
7445861 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017