EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:5280 - gatifloxacin

ChEBI IDCHEBI:5280
ChEBI Namegatifloxacin
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:101712
Last Modified22 February 2017
DownloadsMolfile
FormulaC19H22FN3O4
Net Charge0
Average Mass375.400
Monoisotopic Mass375.15943
SMILESCOc1c(N2CCNC(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12
InChIInChI=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)
InChIKeyXUBOMFCQGDBHNK-UHFFFAOYSA-N
Wikipedia
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.
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:
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
(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  Source
gatifloxacinKEGG DRUG
gatifloxacineWHO MedNet
gatifloxacinumWHO MedNet
gatifloxacinoWHO MedNet
Synonyms  Source
AM 1155KEGG COMPOUND
1-cyclopropyl-6-fluoro- 8-methoxy-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline-3-carboxylic acidChEMBL
1-Cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidChemIDplus
Manual XrefsDatabases
C07661KEGG COMPOUND
D08011KEGG DRUG
DB01044DrugBank
EP230295Patent
US4980470Patent
GatifloxacinWikipedia
LSM-5139LINCS
1280DrugCentral
Registry NumbersSources
Gmelin:2281206Gmelin
Reaxys:7445861Reaxys
CAS:112811-59-3KEGG COMPOUND
CAS:112811-59-3DrugBank
CAS:112811-59-3ChemIDplus
Citations