<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2026-03-31 21:20:03 UTC</creation_date>
  <update_date>2026-08-19 16:13:29 UTC</update_date>
  <accession/>
  <common_name>Amifloxacin</common_name>
  <class>SmallMolecule</class>
  <description>Amifloxacin is an organic compound with the formula C16H19F1N4O3 and an average molecular weight of 334.35 g/mol. Amifloxacin belongs to the quinoline carboxylic acids, a subclass of quinolines and derivatives within the organic compounds. It is categorized as an organoheterocyclic compound.

This compound is found in or released from healthcare, pharmaceuticals, and veterinary products used as antibiotics. Recorded exposure routes for amifloxacin include inhalation and oral administration. In terms of biological activity, the substance acts on two recorded protein targets, serving as an inhibitor of DNA topoisomerase 2-alpha (TOP2A) and DNA topoisomerase 2-beta (TOP2B).</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>2-(2-aminopropan-2-yl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1</synonym>
    <synonym>289-231-8</synonym>
    <synonym>3-Quinolinecarboxylic acid, 6-fluoro-1,4-dihydro-1-(methylamino)-7-(4-methyl-1-piperazinyl)-4-oxo-</synonym>
    <synonym>6-Fluoro-1,4-dihydro-1-(methylamino)-7-(4-methyl-1-piperazinyl)- 4-oxo-3-quinolinecarboxylic acid</synonym>
    <synonym>6-Fluoro-1,4-dihydro-1-(methylamino)-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid</synonym>
    <synonym>6-Fluoro-1-(methylamino)-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid</synonym>
    <synonym>6-Fluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid</synonym>
    <synonym>6-fluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid</synonym>
    <synonym>6-fluoro-1-methylamino-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid</synonym>
    <synonym>6-Fluoro-1-methylamino-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid</synonym>
    <synonym>6-fluoro-1-methylamino-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid</synonym>
    <synonym>6-fluoro-1-methylamino-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid</synonym>
    <synonym>6-fluoro-4-keto-1-methylamino-7-(4-methylpiperazin-1-yl)quinoline-3-carboxylic acid</synonym>
    <synonym>88036-80-0 (MESYLATE SALT)</synonym>
    <synonym>Amifloxacin</synonym>
    <synonym>Amifloxacin (USAN/INN)</synonym>
    <synonym>Amifloxacin [USAN:BAN:INN]</synonym>
    <synonym>Amifloxacine [French]</synonym>
    <synonym>Amifloxacino [Spanish]</synonym>
    <synonym>Amifloxacinum [Latin]</synonym>
    <synonym>EINECS 289-231-8</synonym>
    <synonym>UNII-5TU5227KYQ</synonym>
    <synonym>UNII:5TU5227KYQ</synonym>
  </synonyms>
  <chemical_formula>C16H19F1N4O3</chemical_formula>
  <average_molecular_weight>334.351</average_molecular_weight>
  <monisotopic_moleculate_weight>334.144119</monisotopic_moleculate_weight>
  <iupac_name>6-fluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid</iupac_name>
  <traditional_iupac>amifloxacin</traditional_iupac>
  <cas_registry_number>86393-37-5</cas_registry_number>
  <smiles>CNN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC1</smiles>
  <inchi>InChI=1S/C16H19FN4O3/c1-18-21-9-11(16(23)24)15(22)10-7-12(17)14(8-13(10)21)20-5-3-19(2)4-6-20/h7-9,18H,3-6H2,1-2H3,(H,23,24)</inchi>
  <inchikey>RUXPNBWPIRDVTH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Macrolides and analogues</class>
    <sub_class/>
    <direct_parent>Macrolides and analogues</direct_parent>
    <alternate_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxybenzoic acid derivatives</alternative_parent>
      <alternative_parent>Lactones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dihydroxybenzoic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Macrolide</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Mycotoxins</descriptor>
      <descriptor>macrolide</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>0.2</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.34e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.003</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-fluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>334.351</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>334.144119</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H19F1N4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H19FN4O3/c1-18-21-9-11(16(23)24)15(22)10-7-12(17)14(8-13(10)21)20-5-3-19(2)4-6-20/h7-9,18H,3-6H2,1-2H3,(H,23,24)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RUXPNBWPIRDVTH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>76.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.63</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>-1</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:0x00007f7280cffd38&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB20048</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>55492</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>50111</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000742</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0002425</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
  </targets>
</compound>
