Lomefloxacin (CED0006573)

Record Information
Version1.0
Creation Date2016-05-25 18:24:05 UTC
Update Date2026-08-19 20:12:29 UTC
Accession NumberCHEM022212
Identification
Common NameLomefloxacin
ClassSmall Molecule
Description
Lomefloxacin is an organic compound with the chemical formula C17H19F2N3O3 and an average molecular weight of 351.35 g/mol. Lomefloxacin belongs to the quinoline carboxylic acids, a subclass of quinolines and derivatives within the organic compounds. It is categorized under the superclass of organoheterocyclic compounds. The compound is associated with thirteen recorded sources across several sectors. Within healthcare, pharmaceuticals, and veterinary products, it is found in antibiotics, antiinfectives, quinolone antibacterials, and drugs used for the treatment of tuberculosis. In the food and cookware sector, it is linked to food preservation and the processing of meats. Other sources include household cleaning and consumer products, specifically tobacco smoke filters and soap detergents, as well as electrical and electronic equipment such as electrodes, television systems, hybrid capacitors, electrically stimulated smoking devices, and video games. Recorded routes of exposure for this compound include oral and inhalation. At the molecular level, lomefloxacin interacts with four recorded protein targets. It acts as an inhibitor of DNA gyrase subunit A (gyrA) and DNA topoisomerase 4 subunit A (parC). Additionally, it targets DNA topoisomerase 2-alpha (TOP2A) and DNA topoisomerase 2-beta (TOP2B).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(+-)-1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidChEBI
1,4-Dihydro-6,8-difluoro-1-ethyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidChEBI
LFLXChEBI
LomefloxacineChEBI
LomefloxacinoChEBI
LomefloxacinumChEBI
(+-)-1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylateGenerator
1,4-Dihydro-6,8-difluoro-1-ethyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylateGenerator
Lomefloxacin hydrochlorideHMDB
1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidHMDB
OcacinHMDB
DécalogifloxHMDB
LogifloxHMDB
OkacinHMDB
LomenfloxacinHMDB
OkacynHMDB
Pharmacia brand 1 OF lomefloxacin hydrochlorideHMDB
MaxaquinHMDB
Pharmacia brand 2 OF lomefloxacin hydrochlorideHMDB
Chemical FormulaC17H19F2N3O3
Average Molecular Mass351.348 g/mol
Monoisotopic Mass351.139 g/mol
CAS Registry Number98079-51-7
IUPAC Name1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Traditional Namelomefloxacin
SMILESCCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(N3CCNC(C)C3)C(F)=C12
InChI IdentifierInChI=1S/C17H19F2N3O3/c1-3-21-8-11(17(24)25)16(23)10-6-12(18)15(13(19)14(10)21)22-5-4-20-9(2)7-22/h6,8-9,20H,3-5,7H2,1-2H3,(H,24,25)
InChI KeyZEKZLJVOYLTDKK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monobactams. Monobactams are compounds comprising beta-lactam ring is alone and not fused to another ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentMonobactams
Alternative Parents
Substituents
  • Monobactam
  • 1-phenylazetidine
  • 2-phenylazetidine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fluorobenzene
  • Halobenzene
  • Phenol
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Secondary alcohol
  • Azacycle
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic alcohol
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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 Solubility0.11 g/LALOGPS
logP0ALOGPS
logP-0.39ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)5.64ChemAxon
pKa (Strongest Basic)8.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.88 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity90.11 m³·mol⁻¹ChemAxon
Polarizability34.8 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0076-0059000000-9a020873d71afda0852eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-2146900000-42b37b0f4d359398913cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-a43b3d54ac0a38633f6bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pir-3029000000-16497a4c27f71f504961Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zml-5090000000-69ee2ed1785a83a7efafNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pb9-0009000000-f451e33ca1450f3c318cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-2089000000-c691d19f5e309e23e2d1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9040000000-8eea8088e8777a3cdacbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-7258981d354fc72fb9ddNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0009000000-ee8d89a838e68a0a2cb1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-5059000000-f0e2d4b268337790a2afNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zg0-0049000000-dfb7af6faa9a0d289aa7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0550-0094000000-c2059c294fb1be76130fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004r-0090000000-b404fb16e16898bd86b5Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot 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
4178.0Log mg/kg[2300:7400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
345Quinolone antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
349Drugs for treatment of tuberculosisHealthcare, pharmaceuticals & veterinary productsNot Available
395AntiinfectivesHealthcare, pharmaceuticals & veterinary productsNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureDNA topoisomerase 4 subunit AP0C1U9Staphylococcus aureusPredicted (SEA)0.389246
Click to view 3D structureDNA gyrase subunit AP9WG47Mycobacterium tuberculosisPredicted (SEA)0.311397
Isocitrate lyase structureClick to view 3D structureIsocitrate lyaseP9WKK7Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)0.544945
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)26.3909
Dual specificity protein kinase CLK2 structureClick to view 3D structureDual specificity protein kinase CLK2P49760HumansPredicted (SEA)197.893
Serine/threonine-protein kinase D3 structureClick to view 3D structureSerine/threonine-protein kinase D3O94806HumansPredicted (SEA)184.191
Dual specificity protein kinase CLK4 structureClick to view 3D structureDual specificity protein kinase CLK4Q9HAZ1HumansPredicted (SEA)190.808
V-type proton ATPase subunit B, brain isoform structureClick to view 3D structureV-type proton ATPase subunit B, brain isoformP21281HumansPredicted (SEA)0.467095
Click to view 3D structureGlycoprotein GQ9IH62Henipavirus nipahensePredicted (SEA)7.39568
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)855.485
Aurora kinase B structureClick to view 3D structureAurora kinase BQ96GD4HumansPredicted (SEA)972.025
Ribosomal protein S6 kinase beta-1 structureClick to view 3D structureRibosomal protein S6 kinase beta-1P23443HumansPredicted (SEA)652.376
MAP kinase-activated protein kinase 3 structureClick to view 3D structureMAP kinase-activated protein kinase 3Q16644HumansPredicted (SEA)515.206
Click to view 3D structureSerine/threonine-protein kinase pim-3Q86V86HumansPredicted (SEA)627.387
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)951.473
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)1466.91
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)1100.48
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)986.895
Protein kinase C delta type structureClick to view 3D structureProtein kinase C delta typeQ05655HumansPredicted (SEA)766.971
Serine/threonine-protein kinase PLK1 structureClick to view 3D structureSerine/threonine-protein kinase PLK1P53350HumansPredicted (SEA)836.412
Serine/threonine-protein kinase PAK 1 structureClick to view 3D structureSerine/threonine-protein kinase PAK 1Q13153HumansPredicted (SEA)744.161
cAMP-dependent protein kinase catalytic subunit alpha structureClick to view 3D structurecAMP-dependent protein kinase catalytic subunit alphaP17612HumansPredicted (SEA)948.203
Serine/threonine-protein kinase pim-1 structureClick to view 3D structureSerine/threonine-protein kinase pim-1P11309HumansPredicted (SEA)1152.56
Glycogen synthase kinase-3 alpha structureClick to view 3D structureGlycogen synthase kinase-3 alphaP49840HumansPredicted (SEA)1015.0
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)986.35
Concentrations
Not Available
External Links
DrugBank IDDB00978
HMDB IDHMDB0015113
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLomefloxacin
Chemspider ID3811
ChEBI ID116278
PubChem Compound ID3948
Kegg Compound IDC07078
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11195849
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=3134843
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=3348607
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=3476021