<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:28:00 UTC</creation_date>
  <update_date>2026-08-19 14:54:06 UTC</update_date>
  <accession/>
  <common_name>Ketoprofen</common_name>
  <class>SmallMolecule</class>
  <description>Ketoprofen (C16H14O3) is an organic compound with an average molecular weight of 254.28 g/mol. Ketoprofen belongs to the benzophenones, a subclass of benzene and substituted derivatives within the organic compounds. It functions as a drug (PMC12655400), anti-inflammatory agent (PMC3850105), and analgesic (PMC11124379, PMC11308527). In biological systems, it acts as an inhibitor or other modifier of C-X-C chemokine receptor type 1 (CXCR1), Prostaglandin G/H synthase 1 (PTGS1), and Prostaglandin G/H synthase 2 (PTGS2).

Therapeutically, the compound is used to treat pain (PMC11859530), headache (PMC11459094), fever (PMC13074443), arthritis (PMC11124379, PMC3850105), osteoarthritis (PMC13074443), rheumatoid arthritis (PMC13074443), and gout (PMC11124379). It has a therapeutic effect on inflammation and fever (PMC9899055) and is used for the treatment of inflammation (PMC10884008, PMC13074443). A reported association with the compound is a decrease in bleeding (PMC11124379).

Ketoprofen is identified as an environmental contaminant (PMC10441242). It has been released from 30 recorded sources, including drinking water, indoor air, and healthcare, pharmaceuticals, and veterinary products such as topical products for joint and muscular pain and antiinflammatory and antirheumatic products. Other sources include food, food processing and cookware—specifically the treatment of hops, food preservation, preparation of wort, preparation of malt, and fermentation processes for beer—as well as various household cleaning and consumer products and electrical and electronic equipment. These include amplifiers, antennas, discharge lamps, electric switches, conductors or conductive bodies characterised by the conductive materials, ash trays, bleaching agents, cigar cigarettes, and non electric simulated smoking devices. Recorded exposure routes include oral, rectal, topical, and inhalation.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C16H14O3</chemical_formula>
  <average_molecular_weight>254.2806</average_molecular_weight>
  <monisotopic_moleculate_weight>254.094294314</monisotopic_moleculate_weight>
  <iupac_name>2-(3-benzoylphenyl)propanoic acid</iupac_name>
  <traditional_iupac>ketoprofen</traditional_iupac>
  <cas_registry_number>22071-15-4</cas_registry_number>
  <smiles>CC(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)</inchi>
  <inchikey>DKYWVDODHFEZIM-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>Aryl-phenylketones</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Diphenylmethanes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>2-phenylpropanoic-acid</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>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Diphenylmethane</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>benzophenones</descriptor>
      <descriptor>oxo monocarboxylic acid</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Ketoprofen Action Pathway</name>
      <smpdb_id>SMP0000085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ketoprofen NSAID Action Pathway</name>
      <smpdb_id>SMP0124635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ketoprofen Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143439</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>3.61</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.13e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(3-benzoylphenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>254.2806</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>254.094294314</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H14O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DKYWVDODHFEZIM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.56</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>1</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:0x00007f7224a83d40&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01009</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>3825</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>3693</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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</compound>
