CHEBI:9763 - trovafloxacin

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ChEBI Name trovafloxacin
ChEBI ID CHEBI:9763
Definition A 1,8-naphthyridine derivative that is 4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid bearing additional 2,4-difluorophenyl, fluoro and 6-amino-3-azabicyclo[3.1.0]hex-3-yl substituents at positions 1, 6 and 7 respectively. A broad-spectrum antibiotic that was withdrawn from the market due to risk of liver failure.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H15F3N4O3
Net Charge 0
Average Mass 416.35330
Monoisotopic Mass 416.110
InChI InChI=1S/C20H15F3N4O3/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24/h1-4,7,10-11,16H,5-6,24H2,(H,29,30)/t10-,11+,16+
InChIKey WVPSKSLAZQPAKQ-CDMJZVDBSA-N
SMILES N[C@H]1[C@@H]2CN(C[C@H]12)c1nc2n(cc(C(O)=O)c(=O)c2cc1F)-c1ccc(F)cc1F
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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 )
(via fluoroquinolone antibiotic )
hepatotoxic agent
A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.
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.
DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
antibacterial drug
A drug used to treat or prevent bacterial infections.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing trovafloxacin (CHEBI:9763) has role antibacterial drug (CHEBI:36047)
trovafloxacin (CHEBI:9763) has role antimicrobial agent (CHEBI:33281)
trovafloxacin (CHEBI:9763) has role DNA synthesis inhibitor (CHEBI:59517)
trovafloxacin (CHEBI:9763) has role hepatotoxic agent (CHEBI:50908)
trovafloxacin (CHEBI:9763) has role topoisomerase IV inhibitor (CHEBI:53559)
trovafloxacin (CHEBI:9763) is a 1,8-naphthyridine derivative (CHEBI:73537)
trovafloxacin (CHEBI:9763) is a amino acid (CHEBI:33709)
trovafloxacin (CHEBI:9763) is a azabicycloalkane (CHEBI:38295)
trovafloxacin (CHEBI:9763) is a difluorobenzene (CHEBI:38582)
trovafloxacin (CHEBI:9763) is a fluoroquinolone antibiotic (CHEBI:87211)
trovafloxacin (CHEBI:9763) is a monocarboxylic acid (CHEBI:25384)
trovafloxacin (CHEBI:9763) is a primary amino compound (CHEBI:50994)
trovafloxacin (CHEBI:9763) is a quinolone antibiotic (CHEBI:86324)
trovafloxacin (CHEBI:9763) is a tertiary amino compound (CHEBI:50996)
trovafloxacin (CHEBI:9763) is conjugate base of trovafloxacin(1+) (CHEBI:77569)
Incoming trovafloxacin(1+) (CHEBI:77569) is conjugate acid of trovafloxacin (CHEBI:9763)
IUPAC Name
7-[(1R,5S,6s)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
INNs Sources
trovafloxacin KEGG DRUG
trovafloxacine WHO MedNet
trovafloxacino WHO MedNet
trovafloxacinum WHO MedNet
Manual Xrefs Databases
2777 DrugCentral
C07664 KEGG COMPOUND
D08654 KEGG DRUG
DB00685 DrugBank
HMDB0014823 HMDB
Trovafloxacin Wikipedia
View more database links
Registry Numbers Types Sources
147059-72-1 CAS Registry Number KEGG COMPOUND
147059-72-1 CAS Registry Number ChemIDplus
8172628 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20022474 PubMed citation Europe PMC
20462743 PubMed citation Europe PMC
20538741 PubMed citation Europe PMC
20655887 PubMed citation Europe PMC
21151465 PubMed citation Europe PMC
22305082 PubMed citation Europe PMC
23727874 PubMed citation Europe PMC
24097668 PubMed citation Europe PMC
24525298 PubMed citation Europe PMC
Last Modified
22 February 2017