Trovafloxacin mesylate (CHEM018504)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:17:51 UTC
Update Date2016-11-09 01:15:49 UTC
Accession NumberCHEM018504
Identification
Common NameTrovafloxacin mesylate
ClassSmall Molecule
DescriptionA 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 A broad-spectrum antibiotic that was withdrawn from the market due to risk of liver failure.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Trovafloxacin methanesulfonateChEBI
Trovafloxacin monomesylateChEBI
Trovafloxacin monomethanesulfonateChEBI
TrovanChEBI
Trovafloxacin methanesulfonic acidGenerator
Trovafloxacin methanesulphonateGenerator
Trovafloxacin methanesulphonic acidGenerator
Trovafloxacin monomesylic acidGenerator
Trovafloxacin monomethanesulfonic acidGenerator
Trovafloxacin monomethanesulphonateGenerator
Trovafloxacin monomethanesulphonic acidGenerator
Trovafloxacin mesylic acidGenerator
7-[(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]Hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate
methanesulfonate
methanesulphonate
7-[(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]Hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
methanesulphonic acid
Chemical FormulaC21H19F3N4O6S
Average Molecular Mass512.460 g/mol
Monoisotopic Mass512.098 g/mol
CAS Registry Number147059-75-4
IUPAC Name7-[(1R,5S,6S)-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; methanesulfonic acid
Traditional Name7-[(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; methanesulfonic acid
SMILESCS(O)(=O)=O.[H][C@@]12CN(C[C@]1([H])[C@H]2N)C1=NC2=C(C=C1F)C(=O)C(=CN2C1=C(F)C=C(F)C=C1)C(O)=O
InChI IdentifierInChI=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+;
InChI KeyDYNZICQDCVYXFW-AHZSKCOESA-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 FrameworkNot Available
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Polarizability38.33 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000090000-6207279ed247511f2370Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000090000-6207279ed247511f2370Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000090000-6207279ed247511f2370Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-804685c92f1033eca3bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000090000-804685c92f1033eca3bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0000090000-804685c92f1033eca3bfSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT000992
HMDB IDNot Available
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 IDNot Available
ChEBI ID77568
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11684402
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14718297
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23986008
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=9222073