Trovafloxacin (CED0006543)

Record Information
Version1.0
Creation Date2016-05-25 18:22:17 UTC
Update Date2026-08-20 04:44:19 UTC
Accession NumberCHEM022159
Identification
Common NameTrovafloxacin
ClassSmall Molecule
Description
Trovafloxacin is an organic compound with the formula C20H15F3N4O3 and an average molecular weight of 416.35 g/mol. Trovafloxacin belongs to the naphthyridines, a subclass of diazanaphthalenes within the organic compounds. It is further classified as an organoheterocyclic compound. The compound is found in or released from three recorded sources: antennas within electrical and electronic equipment, and quinolone antibacterials and antibiotics within healthcare, pharmaceuticals, and veterinary products. Recorded exposure routes for this substance include intravenous, oral, and inhalation. In terms of biological activity, trovafloxacin acts as an inhibitor or modulator of four recorded protein targets. These include DNA gyrase subunit A (gyrA), DNA gyrase subunit B (gyrB), DNA topoisomerase 4 subunit A (parC), and DNA topoisomerase 2-alpha (TOP2A).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
TVFXHMDB
7-[(1R,5S)-6-Amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateHMDB
TrovafloxacinMeSH
Chemical FormulaC20H15F3N4O3
Average Molecular Mass416.353 g/mol
Monoisotopic Mass416.110 g/mol
CAS Registry Number147059-72-1
IUPAC Name7-[(1R,5S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Traditional Nametrovafloxacin
SMILES[H][C@@]12CN(C[C@]1([H])C2N)C1=C(F)C=C2C(=O)C(=CN(C3=C(F)C=C(F)C=C3)C2=N1)C(O)=O
InChI IdentifierInChI=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?
InChI KeyWVPSKSLAZQPAKQ-SOSAQKQKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassNaphthyridines
Direct ParentNaphthyridine carboxylic acids and derivatives
Alternative Parents
Substituents
  • Naphthyridine carboxylic acid
  • Fluoroquinolone
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Dialkylarylamine
  • 4-aminopiperidine
  • Aminopyridine
  • Halobenzene
  • Fluorobenzene
  • Aryl fluoride
  • Piperidine
  • Aryl halide
  • Monocyclic benzene moiety
  • Pyridine
  • Imidolactam
  • Benzenoid
  • Pyrrolidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organofluoride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.07 g/LALOGPS
logP0.86ALOGPS
logP0.14ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)5.41ChemAxon
pKa (Strongest Basic)9.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity101.04 m³·mol⁻¹ChemAxon
Polarizability38.34 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000b-2119000000-91742a1b93c82cf212d5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-7003900000-4818baa2c2a4f74b2220Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gb9-0006900000-2710bf3a67a56277c91aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fyk-0009200000-09205f5639aced9d56b1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2109000000-c9470417cb99415a7647Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gi0-0009300000-889348bd48600cb6c1a5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fk9-0019000000-74abce38948c12f68820Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kdi-0269000000-576e128582edeb4bb363Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0000900000-3867ec761451154ce3c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0009000000-73e5733bc87ce9b57a25Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0v7j-0019000000-0c5ac23c528b63c072a6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gb9-0008900000-f2e46d3c5f677f467399Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-cecc830cc169437c1861Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0129000000-26a3bdcab7848d604140Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2026.0Log mg/kg[1100:3600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
345Quinolone antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
1 pathway
Trovafloxacin Drug Metabolism Action Pathway
Trovafloxacin Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureDNA topoisomerase 4 subunit AP0C1U9Staphylococcus aureusPredicted (SEA)2.33548
Isocitrate lyase structureClick to view 3D structureIsocitrate lyaseP9WKK7Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)1.55698
DNA polymerase I, thermostable structureClick to view 3D structureDNA polymerase I, thermostableP19821Thermus aquaticusPredicted (SEA)0.233548
V-type proton ATPase subunit B, brain isoform structureClick to view 3D structureV-type proton ATPase subunit B, brain isoformP21281HumansPredicted (SEA)1.01204
Dipeptidyl peptidase 4 structureClick to view 3D structureDipeptidyl peptidase 4P27487HumansPredicted (SEA)78.2385
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)2425.24
Dual specificity protein kinase CLK2 structureClick to view 3D structureDual specificity protein kinase CLK2P49760HumansPredicted (SEA)1573.41
Serine/threonine-protein kinase D3 structureClick to view 3D structureSerine/threonine-protein kinase D3O94806HumansPredicted (SEA)1461.39
Dual specificity protein kinase CLK4 structureClick to view 3D structureDual specificity protein kinase CLK4Q9HAZ1HumansPredicted (SEA)1574.03
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)1850.32
Aurora kinase B structureClick to view 3D structureAurora kinase BQ96GD4HumansPredicted (SEA)2023.38
Ribosomal protein S6 kinase beta-1 structureClick to view 3D structureRibosomal protein S6 kinase beta-1P23443HumansPredicted (SEA)1447.22
Click to view 3D structureSerine/threonine-protein kinase pim-3Q86V86HumansPredicted (SEA)1265.98
MAP kinase-activated protein kinase 3 structureClick to view 3D structureMAP kinase-activated protein kinase 3Q16644HumansPredicted (SEA)1232.98
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)655.568
MAP kinase-activated protein kinase 2 structureClick to view 3D structureMAP kinase-activated protein kinase 2P49137HumansPredicted (SEA)1700.62
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)2730.95
cAMP-dependent protein kinase catalytic subunit alpha structureClick to view 3D structurecAMP-dependent protein kinase catalytic subunit alphaP17612HumansPredicted (SEA)2018.24
Serine/threonine-protein kinase pim-1 structureClick to view 3D structureSerine/threonine-protein kinase pim-1P11309HumansPredicted (SEA)2403.67
Click to view 3D structureMitogen-activated protein kinase kinase kinase kinase 2Q12851HumansPredicted (SEA)1956.27
Ribosomal protein S6 kinase alpha-3 structureClick to view 3D structureRibosomal protein S6 kinase alpha-3P51812HumansPredicted (SEA)2049.3
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)3008.09
Glycogen synthase kinase-3 alpha structureClick to view 3D structureGlycogen synthase kinase-3 alphaP49840HumansPredicted (SEA)2176.66
Mitogen-activated protein kinase kinase kinase kinase 4 structureClick to view 3D structureMitogen-activated protein kinase kinase kinase kinase 4O95819HumansPredicted (SEA)2115.4
Casein kinase I isoform alpha structureClick to view 3D structureCasein kinase I isoform alphaP48729HumansPredicted (SEA)1969.2
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0014823
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTrovafloxacin
Chemspider ID56670
ChEBI IDNot Available
PubChem Compound ID62959
Kegg Compound IDC07664
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References