<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 06:36:05 UTC</creation_date>
  <update_date>2026-08-19 09:47:43 UTC</update_date>
  <accession/>
  <common_name>Nepafenac</common_name>
  <class>SmallMolecule</class>
  <description>Nepafenac is an organic compound with the formula C15H14N2O2 and an average molecular weight of 254.28 g/mol. Nepafenac belongs to the benzophenones, a subclass of benzene and substituted derivatives within the organic compounds. It is recorded as being found in or released from two sources: healthcare, pharmaceuticals &amp; veterinary products (specifically antiinflammatory agents) and household cleaning &amp; consumer products (specifically non electric simulated smoking devices). The recorded exposure route for this compound is ophthalmic.

At the molecular level, nepafenac interacts with two recorded protein targets. It acts as an inhibitor of Prostaglandin G/H synthase 1 (PTGS1) and Prostaglandin G/H synthase 2 (PTGS2).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C15H14N2O2</chemical_formula>
  <average_molecular_weight>254.2839</average_molecular_weight>
  <monisotopic_moleculate_weight>254.105527702</monisotopic_moleculate_weight>
  <iupac_name>2-(2-amino-3-benzoylphenyl)acetamide</iupac_name>
  <traditional_iupac>nepafenac</traditional_iupac>
  <cas_registry_number>78281-72-8</cas_registry_number>
  <smiles>NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N</smiles>
  <inchi>InChI=1S/C15H14N2O2/c16-13(18)9-11-7-4-8-12(14(11)17)15(19)10-5-2-1-3-6-10/h1-8H,9,17H2,(H2,16,18)</inchi>
  <inchikey>QEFAQIPZVLVERP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzophenones</sub_class>
    <direct_parent>Benzophenones</direct_parent>
    <alternate_parents>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Aryl-phenylketones</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Diphenylmethanes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylacetamides</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl ketone</substituent>
      <substituent>Aryl-phenylketone</substituent>
      <substituent>Benzophenone</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Diphenylmethane</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylacetamide</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>monocarboxylic acid amide</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Nepafenac Action Pathway</name>
      <smpdb_id>SMP0000702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nepafenac NSAID Action Pathway</name>
      <smpdb_id>SMP0124581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nepafenac Drug Metabolism</name>
      <smpdb_id>SMP0130823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nepafenac Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0144138</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>2.08</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.97e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(2-amino-3-benzoylphenyl)acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>254.2839</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>254.105527702</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)CC1=CC=CC(C(=O)C2=CC=CC=C2)=C1N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H14N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H14N2O2/c16-13(18)9-11-7-4-8-12(14(11)17)15(19)10-5-2-1-3-6-10/h1-8H,9,17H2,(H2,16,18)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QEFAQIPZVLVERP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>74.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</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:0x00007f7273a66d68&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB06802</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>151075</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>133160</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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      <target_id>BE0000017</target_id>
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      <target_id>BE0000262</target_id>
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  </targets>
</compound>
