Norfloxacin (CED0002307)

Record Information
Version1.0
Creation Date2016-05-22 04:24:09 UTC
Update Date2026-08-19 15:55:28 UTC
Accession NumberCHEM017497
Identification
Common NameNorfloxacin
ClassSmall Molecule
Description
Norfloxacin (C16H18FN3O3) is an organic compound with an average molecular weight of 319.33 g/mol. Norfloxacin belongs to the quinoline carboxylic acids, a subclass of quinolines and derivatives within the organic compounds. This substance is found in or released from 25 recorded sources, including drinking water and water supply (drinking water), healthcare, pharmaceuticals & veterinary products (quinolone antibacterials, combinations of antibacterials, antiinfectives, antibiotics), and food, food processing & cookware (food preservation, processing meats). Additional sources include household cleaning & consumer products (cigar cigarettes, non electric simulated smoking devices, other smoking requisites, perfumes within detergents and soaps, pipe accessories, and 4 more) and electrical & electronic equipment (conductors or conductive bodies characterised by the conductive materials, electric hearing aids, electrically stimulated smoking devices, electrodes, hybrid capacitors, and 4 more). Recorded exposure routes include oral, ophthalmic, and inhalation. At the molecular level, there are 5 recorded protein targets for norfloxacin. It acts as an inhibitor/modulator of DNA gyrase subunit A (gyrA), DNA topoisomerase 4 subunit A (parC), DNA topoisomerase 2-alpha (TOP2A), DNA topoisomerase 2-beta (TOP2B), and one other protein. Regarding health effects, norfloxacin is associated with obesity (PMC11271401).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
1,4-Dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acidChEBI
1-Ethyl-6-fluor-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-chinolincarbonsaeureChEBI
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acidChEBI
NFLXChEBI
NorfloxacineChEBI
NorfloxacinoChEBI
NorfloxacinumChEBI
NoroxinKegg
1,4-Dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylateGenerator
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylateGenerator
Merck brand OF norfloxacinHMDB
Norfloxacin merck brandHMDB
Chemical FormulaC16H18FN3O3
Average Molecular Mass319.331 g/mol
Monoisotopic Mass319.133 g/mol
CAS Registry Number70458-96-7
IUPAC Name1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
Traditional Namenorfloxacin
SMILESCCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCNCC1
InChI IdentifierInChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)
InChI KeyOGJPXUAPXNRGGI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Dihydropyridine
  • Hydroxypyridine
  • Hydropyridine
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid
  • Cyclic ketone
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • 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 Solubility1.01 g/LALOGPS
logP-0.47ALOGPS
logP-0.92ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)5.77ChemAxon
pKa (Strongest Basic)8.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.88 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity85.48 m³·mol⁻¹ChemAxon
Polarizability32.26 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 Spectrumsplash10-0ufu-1092000000-bf3fd3d7faa91b8515deNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00b9-2029000000-1c3a70fd1922acc3da89Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0910000000-71f0a353a8e37a26b402Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0019000000-209bfb114ccbb6d9e304Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0069000000-4d54becdaa4caedbe3b2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0391000000-a84cfa736c2dcec4d545Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ufr-0069000000-246d2ae5a6ec6a55d6b1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-f809266e62551b06d730Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fmi-0039000000-b7128cd18b98a04daf9eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0069000000-d5c4d2c4b68d5f6d03a2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ue9-0095000000-901dbfc8f7d02a135c4dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0491000000-be9683c47fbf7a3cb0baNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0970000000-90dc103f49990c57d26fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-13d5054c01078e14d8f0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fmi-0039000000-74150f6e5c4d2dcba6abNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0059000000-dd2ee816e5228385835dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f89-0195000000-596094ef32a4ddd39544Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0491000000-20c74694b378fdb752b2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0970000000-06c84236dac00c44e42eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ufr-0069000000-5c4650a9bab59ded6701Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0910000000-71f0a353a8e37a26b402Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1398000000-86efb47466226acbabf9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ue9-0096000000-f3f841a319566912af02Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0391000000-c411209f460d7eaca3a2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0019000000-1a2bb8c3e9c6d931087dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0391000000-55a58d2233032fc050d9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-9ba41b8d82297e1ac319Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0069000000-0d5588e0eaecc6bd08d5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-f7d48619a0d8eb02627eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-fd7519b3aaaecbb56388Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0069000000-1b53dedb0b586577e396Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0059000000-65124d735edfb5212d4fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fmi-0039000000-b4b286e4c36848e62afcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fmi-0039000000-8d353315d0aa10d66969Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0970000000-98f1899841689cbee2f1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ufr-0069000000-7cce5f7c263b59edfa16Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-f809266e62551b06d730Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-9ab62d2e583b1c4bf3ffNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0391000000-5e8e54dd831193d9d746Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-58121fa65fd6bb68db1eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f89-0096000000-97e74ebc83184e3278deNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0069000000-4d54becdaa4caedbe3b2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0980000000-8d221256f6ec3a3b419cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ufr-0069000000-130cb1fc7d464184bb19Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0391000000-a84cfa736c2dcec4d545Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0029000000-71b732750ca6ae35eeafNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fmi-1095000000-f6c15b3b64948217c713Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-3190000000-5eb0c3a916bc08140fc5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00xr-0095000000-ecc84ee43ade0cae1058Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1090000000-39e213194d7a6b6854f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000f-5290000000-7214f42f26930bf54144Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-e4240570e4fb5d4de7a5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0039000000-912d12d8c144fc938755Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05gi-0091000000-63f6afc2a7994451b283Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gi0-0095000000-016c71a73fb8cf3c2034Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6w-0090000000-a2eb1b87489b6e09fe55Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6y-0090000000-0c4d33c78a5a7d70e8bbNot 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
2721.0Log mg/kg[1500:4800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
obesityassociated_withNot AvailablePMC11271401
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
345Quinolone antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
346Combinations of antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
395AntiinfectivesHealthcare, pharmaceuticals & veterinary productsNot 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
527MagnetsElectrical & 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
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold 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
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal 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
619Manicure PedicurePersonal 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
Isocitrate lyase structureClick to view 3D structureIsocitrate lyaseP9WKK7Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)0.0778492
Click to view 3D structureDNA topoisomerase 4 subunit AP0C1U9Staphylococcus aureusPredicted (SEA)0.155698
Click to view 3D structureGlycoprotein GQ9IH62Henipavirus nipahensePredicted (SEA)0.155698
V-type proton ATPase subunit B, brain isoform structureClick to view 3D structureV-type proton ATPase subunit B, brain isoformP21281HumansPredicted (SEA)0.0778492
Bromodomain-containing protein 4 structureClick to view 3D structureBromodomain-containing protein 4O60885HumansPredicted (SEA)42.1943
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)35.8106
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)507.499
Click to view 3D structureCytochrome P450 2J2P51589HumansPredicted (SEA)2.17978
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)196.647
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)363.712
Click to view 3D structureDNA gyrase subunit AP9WG47Mycobacterium tuberculosisPredicted (SEA)1.55698
Dual specificity protein kinase CLK2 structureClick to view 3D structureDual specificity protein kinase CLK2P49760HumansPredicted (SEA)980.667
Serine/threonine-protein kinase D3 structureClick to view 3D structureSerine/threonine-protein kinase D3O94806HumansPredicted (SEA)905.309
Dual specificity protein kinase CLK4 structureClick to view 3D structureDual specificity protein kinase CLK4Q9HAZ1HumansPredicted (SEA)972.726
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)575.539
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)656.269
Click to view 3D structure5-hydroxytryptamine receptor 1BP28564Rattus norvegicusPredicted (SEA)219.768
Click to view 3D structureD(1A) dopamine receptorP18901Rattus norvegicusPredicted (SEA)278.389
Click to view 3D structureHistamine H3 receptorQ9QYN8Rattus norvegicusPredicted (SEA)122.068
MAP kinase-interacting serine/threonine-protein kinase 2 structureClick to view 3D structureMAP kinase-interacting serine/threonine-protein kinase 2Q9HBH9HumansPredicted (SEA)1062.17
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)664.755
Serine/threonine-protein kinase PAK 1 structureClick to view 3D structureSerine/threonine-protein kinase PAK 1Q13153HumansPredicted (SEA)1209.31
LIM domain kinase 1 structureClick to view 3D structureLIM domain kinase 1P53667HumansPredicted (SEA)1187.98
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)1817.47
Click to view 3D structureSerine/threonine-protein kinase pim-3Q86V86HumansPredicted (SEA)1246.29
Concentrations
Not Available
External Links
DrugBank IDDB01059
HMDB IDHMDB0015192
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNorfloxacin
Chemspider ID4380
ChEBI ID100246
PubChem Compound ID4539
Kegg Compound IDC06687
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Goldstein EJ: Norfloxacin, a fluoroquinolone antibacterial agent. Classification, mechanism of action, and in vitro activity. Am J Med. 1987 Jun 26;82(6B):3-17.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=3317294
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=3908074
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=6211142
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6224685
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=6234465
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=6454381
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=6461606