Enoxacin (CED0005860)

Record Information
Version1.0
Creation Date2016-05-22 03:40:28 UTC
Update Date2026-08-19 10:34:13 UTC
Accession NumberCHEM016686
Identification
Common NameEnoxacin
ClassSmall Molecule
Description
Enoxacin is an organic compound with the chemical formula C15H17FN4O3 and an average molecular weight of 320.32 g/mol. Enoxacin belongs to the naphthyridines, a subclass of diazanaphthalenes within the organic compounds. It is categorized under the superclass of organoheterocyclic compounds. The compound is utilized as an antibiotic within healthcare, pharmaceuticals, and veterinary products. It has been identified in or released from 19 recorded sources. These include drinking water and water supply systems, as well as food preservation and the processing of meats. It is also associated with household cleaning and consumer products, specifically tobacco pipes, soap detergents, cigar cigarettes, pipe accessories, and tobacco smoke filters. Furthermore, it is found in electrical and electronic equipment, including amplifiers, antennas, electric hearing aids, electrically stimulated smoking devices, and conductors or conductive bodies characterized by the conductive materials. Exposure to enoxacin occurs through oral and inhalation routes. At a molecular level, enoxacin interacts with four recorded protein targets. It functions 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 Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acidChEBI
1-Ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acidChEBI
EnoxacineChEBI
EnoxacinoChEBI
EnoxacinumChEBI
ENXKegg
PenetrexKegg
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylateGenerator
1-Ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylateGenerator
EnoxinHMDB
Rhône poulenc rorer brand OF enoxacin sesquihydrateHMDB
EnoxorHMDB
Enoxacin sesquihydrateHMDB
Faulding brand OF enoxacinHMDB
Pierre fabre brand OF enoxacin sesquihydrateHMDB
Rhône-poulenc rorer brand OF enoxacin sesquihydrateHMDB
Sesquihydrate, enoxacinHMDB
Chemical FormulaC15H17FN4O3
Average Molecular Mass320.319 g/mol
Monoisotopic Mass320.128 g/mol
CAS Registry Number74011-58-8
IUPAC Name1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Traditional Nameenoxacin
SMILESCCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(N=C12)N1CCNCC1
InChI IdentifierInChI=1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)
InChI KeyIDYZIJYBMGIQMJ-UHFFFAOYSA-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
  • N-arylpiperazine
  • Pyridinylpiperazine
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Dialkylarylamine
  • Aminopyridine
  • Aryl fluoride
  • Aryl halide
  • 1,4-diazinane
  • Piperazine
  • Imidolactam
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Azacycle
  • Secondary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility1.09 g/LALOGPS
logP-0.97ALOGPS
logP-0.98ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)5.5ChemAxon
pKa (Strongest Basic)8.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.77 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.95 m³·mol⁻¹ChemAxon
Polarizability31.63 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0zi0-1093000000-241451e66e16daabab83Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00b9-2039000000-3aaed983f26fc10675b9Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0pc0-2691000000-70495182f5d53b3e2f3eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-c343d2455564f9c283abNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0039000000-c8fb064ca8dcd22fd051Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0069000000-6f1cc68c72c995af1700Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fr-0195000000-f089fb10889524908bb9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0391000000-342a8fc923e2f74b2c2fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0970000000-ad4c54479d1e64d34d71Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0pc0-2691000000-70495182f5d53b3e2f3eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0970000000-bb0d7bb58daaabaa5d30Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fr-0095000000-e5aecf8dae20a8173ba7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0391000000-9c0a1a78d2583bd88339Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0069000000-0e21ce47b095471d4c88Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0039000000-56c5deec0bec46a6ccc6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-be580c5bfc772c508991Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0029000000-b768a8766a208143ef4dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fi9-3095000000-4d791244c2706826943aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002f-3090000000-449abf1ea9e4d691dee5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00or-0094000000-2dfdf64dcd801c343137Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002b-0190000000-6184732185fc1f37ecefNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000e-6490000000-d025aca1fd56c040e757Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-a42c0b05ac20f28b16b2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0029000000-7012f2139eff8aba307fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0059-0091000000-8e32867f3fee05370a41Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0axs-0092000000-89be0bf06b51a26e9b3dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-bbe88efb18ff81eade78Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0290000000-bd66a9a90e8ca9009f59Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H 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
2282.0Log mg/kg[1300:4100]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & 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
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial 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
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
633Azo DyesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
V-type proton ATPase subunit B, brain isoform structureClick to view 3D structureV-type proton ATPase subunit B, brain isoformP21281HumansPredicted (SEA)0.0778492
Click to view 3D structureDNA topoisomerase 4 subunit AP0C1U9Staphylococcus aureusPredicted (SEA)0.467095
Isocitrate lyase structureClick to view 3D structureIsocitrate lyaseP9WKK7Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)0.389246
RISC-loading complex subunit TARBP2 structureClick to view 3D structureRISC-loading complex subunit TARBP2Q15633HumansPredicted (SEA)0.155698
Click to view 3D structureGlycoprotein GQ9IH62Henipavirus nipahensePredicted (SEA)4.43741
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)132.733
Click to view 3D structureDNA gyrase subunit AP9WG47Mycobacterium tuberculosisPredicted (SEA)1.71268
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)508.511
Bromodomain-containing protein 4 structureClick to view 3D structureBromodomain-containing protein 4O60885HumansPredicted (SEA)265.466
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)2134.16
Dual specificity protein kinase CLK2 structureClick to view 3D structureDual specificity protein kinase CLK2P49760HumansPredicted (SEA)1213.67
Serine/threonine-protein kinase D3 structureClick to view 3D structureSerine/threonine-protein kinase D3O94806HumansPredicted (SEA)1120.41
Dual specificity protein kinase CLK4 structureClick to view 3D structureDual specificity protein kinase CLK4Q9HAZ1HumansPredicted (SEA)1207.13
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)515.284
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)946.335
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)1047.93
Aurora kinase B structureClick to view 3D structureAurora kinase BQ96GD4HumansPredicted (SEA)1966.16
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)797.02
MAP kinase-activated protein kinase 3 structureClick to view 3D structureMAP kinase-activated protein kinase 3Q16644HumansPredicted (SEA)1224.72
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)957.545
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)857.898
Serine/threonine-protein kinase PAK 1 structureClick to view 3D structureSerine/threonine-protein kinase PAK 1Q13153HumansPredicted (SEA)1443.25
LIM domain kinase 1 structureClick to view 3D structureLIM domain kinase 1P53667HumansPredicted (SEA)1406.66
Click to view 3D structure5-hydroxytryptamine receptor 1BP28564Rattus norvegicusPredicted (SEA)331.871
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)1931.44
Concentrations
Not Available
External Links
DrugBank IDDB00467
HMDB IDHMDB0014610
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEnoxacin
Chemspider ID3116
ChEBI ID157175
PubChem Compound ID3229
Kegg Compound IDC06979
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16644219
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=8741236