CHEBI:77568 - trovafloxacin mesylate

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ChEBI Name trovafloxacin mesylate
ChEBI ID CHEBI:77568
Definition A methanesulfonate (mesylate) salt prepared from equimolar amounts of trovafloxacin and methanesulfonic acid. A broad-spectrum antibiotic that was withdrawn from the market due to risk of liver failure.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 C21H19F3N4O6S
Net Charge 0
Average Mass 512.45900
Monoisotopic Mass 512.09774
InChI InChI=1S/C20H15F3N4O3.CH4O3S/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;1-5(2,3)4/h1-4,7,10-11,16H,5-6,24H2,(H,29,30);1H3,(H,2,3,4)/t10-,11+,16+;
InChIKey DYNZICQDCVYXFW-AHZSKCOESA-N
SMILES CS(O)(=O)=O.N[C@H]1[C@@H]2CN(C[C@H]12)c1nc2n(cc(C(O)=O)c(=O)c2cc1F)-c1ccc(F)cc1F
Roles Classification
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
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.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
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ChEBI Ontology
Outgoing trovafloxacin mesylate (CHEBI:77568) has part trovafloxacin(1+) (CHEBI:77569)
trovafloxacin mesylate (CHEBI:77568) has role antibacterial drug (CHEBI:36047)
trovafloxacin mesylate (CHEBI:77568) has role antimicrobial agent (CHEBI:33281)
trovafloxacin mesylate (CHEBI:77568) has role DNA synthesis inhibitor (CHEBI:59517)
trovafloxacin mesylate (CHEBI:77568) has role hepatotoxic agent (CHEBI:50908)
trovafloxacin mesylate (CHEBI:77568) has role topoisomerase IV inhibitor (CHEBI:53559)
trovafloxacin mesylate (CHEBI:77568) is a methanesulfonate salt (CHEBI:38037)
IUPAC Names
(1R,5S,6s)-3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5-oxo-5,8-dihydro-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hexan-6-aminium methanesulfonate
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 methanesulfonate
Synonyms Sources
trovafloxacin methanesulfonate ChEBI
trovafloxacin monomesylate ChEBI
Trovafloxacin monomethanesulfonate ChemIDplus
Brand Name Source
Trovan KEGG DRUG
Manual Xrefs Databases
D02123 KEGG DRUG
DB00685 DrugBank
EP0930068 Patent
NZ553119 Patent
Trovafloxacin Wikipedia
View more database links
Registry Numbers Types Sources
147059-75-4 CAS Registry Number ChemIDplus
8180672 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11684402 PubMed citation Europe PMC
14718297 PubMed citation Europe PMC
23986008 PubMed citation Europe PMC
9222073 PubMed citation Europe PMC
Last Modified
04 March 2014