CHEBI:101853 - gemifloxacin

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ChEBI Name gemifloxacin
ChEBI ID CHEBI:101853
Definition A 1,4-dihydro-1,8-naphthyridine with a carboxy group at the 3-position, an oxo sustituent at the 4-position, a fluoro substituent at the 5-position and a substituted pyrrolin-1-yl group at the 7-position.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H20FN5O4
Net Charge 0
Average Mass 389.38090
Monoisotopic Mass 389.150
InChI InChI=1S/C18H20FN5O4/c1-28-22-14-8-23(6-9(14)5-20)17-13(19)4-11-15(25)12(18(26)27)7-24(10-2-3-10)16(11)21-17/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27)/b22-14+
InChIKey ZRCVYEYHRGVLOC-HYARGMPZSA-N
SMILES CO\N=C1/CN(CC1CN)c1nc2n(cc(C(O)=O)c(=O)c2cc1F)C1CC1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
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ChEBI Ontology
Outgoing gemifloxacin (CHEBI:101853) has role antibacterial drug (CHEBI:36047)
gemifloxacin (CHEBI:101853) has role antimicrobial agent (CHEBI:33281)
gemifloxacin (CHEBI:101853) has role topoisomerase IV inhibitor (CHEBI:53559)
gemifloxacin (CHEBI:101853) is a 1,8-naphthyridine derivative (CHEBI:73537)
gemifloxacin (CHEBI:101853) is a fluoroquinolone antibiotic (CHEBI:87211)
gemifloxacin (CHEBI:101853) is a monocarboxylic acid (CHEBI:25384)
gemifloxacin (CHEBI:101853) is a quinolone antibiotic (CHEBI:86324)
Incoming gemifloxacin mesylate (CHEBI:53749) has part gemifloxacin (CHEBI:101853)
IUPAC Name
7-[3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
INN Source
gemifloxacin KEGG DRUG
Manual Xrefs Databases
1286 DrugCentral
D08012 KEGG DRUG
DB01155 DrugBank
EP688772 Patent
Gemifloxacin Wikipedia
US5633262 Patent
View more database links
Registry Numbers Types Sources
175463-14-6 CAS Registry Number ChemIDplus
175463-14-6 CAS Registry Number DrugBank
8361408 Beilstein Registry Number Beilstein
Last Modified
22 February 2017