<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:40:28 UTC</creation_date>
  <update_date>2026-08-19 10:34:13 UTC</update_date>
  <accession/>
  <common_name>Enoxacin</common_name>
  <class>SmallMolecule</class>
  <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).</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C15H17FN4O3</chemical_formula>
  <average_molecular_weight>320.3189</average_molecular_weight>
  <monisotopic_moleculate_weight>320.128468635</monisotopic_moleculate_weight>
  <iupac_name>1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid</iupac_name>
  <traditional_iupac>enoxacin</traditional_iupac>
  <cas_registry_number>74011-58-8</cas_registry_number>
  <smiles>CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(N=C12)N1CCNCC1</smiles>
  <inchi>InChI=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>
  <inchikey>IDYZIJYBMGIQMJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazanaphthalenes</class>
    <sub_class>Naphthyridines</sub_class>
    <direct_parent>Naphthyridine carboxylic acids and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyridines and derivatives</alternative_parent>
      <alternative_parent>Aryl fluorides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Dialkylarylamines</alternative_parent>
      <alternative_parent>Fluoroquinolones</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-arylpiperazines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organofluorides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinecarboxylic acids</alternative_parent>
      <alternative_parent>Pyridinylpiperazines</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1,4-diazinane</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyridine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Aryl fluoride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkylarylamine</substituent>
      <substituent>Fluoroquinolone</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-arylpiperazine</substituent>
      <substituent>Naphthyridine carboxylic acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organofluoride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Piperazine</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridine carboxylic acid</substituent>
      <substituent>Pyridine carboxylic acid or derivatives</substituent>
      <substituent>Pyridinylpiperazine</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>1,8-naphthyridine derivative</descriptor>
      <descriptor>N-arylpiperazine</descriptor>
      <descriptor>amino acid</descriptor>
      <descriptor>fluoroquinolone antibiotic</descriptor>
      <descriptor>monocarboxylic acid</descriptor>
      <descriptor>quinolone antibiotic</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Enoxacin Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142921</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-1</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.09e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>320.3189</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>320.128468635</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(N=C12)N1CCNCC1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H17FN4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=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)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IDYZIJYBMGIQMJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>85.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bf3350be8&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00467</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>3229</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>3116</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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