<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:43:29 UTC</creation_date>
  <update_date>2026-08-22 02:55:09 UTC</update_date>
  <accession/>
  <common_name>Ezetimibe</common_name>
  <class>SmallMolecule</class>
  <description>Ezetimibe is an organic compound with the formula C24H21F2NO3 and an average molecular weight of 409.43 g/mol. Ezetimibe belongs to the beta lactams, a subclass of lactams within the organic compounds. It is classified as an organoheterocyclic compound.

This compound acts as a biological drug (PMC3667667). Its protein targets include Aminopeptidase N (ANPEP), Sterol O-acyltransferase 1 (SOAT1), and the NPC1-like intracellular cholesterol transporter 1 (NPC1L1), which it inhibits or otherwise affects. Regarding health effects, ezetimibe has a therapeutic effect on atherosclerosis.

Ezetimibe is identified in 17 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used as a lipid modifying agent. It is also found in food, food processing, and cookware specifically for the preparation of wine or sparkling wine. Additionally, it is recorded in household cleaning and consumer products, including other smoking requisites and non electric simulated smoking devices. It is also present in electrical and electronic equipment, including antennas, amplifiers, coils, auxiliary devices, adjustable resistors, and eight other items. The recorded route of exposure for this compound is oral.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C24H21F2NO3</chemical_formula>
  <average_molecular_weight>409.4252</average_molecular_weight>
  <monisotopic_moleculate_weight>409.148949953</monisotopic_moleculate_weight>
  <iupac_name>(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one</iupac_name>
  <traditional_iupac>ezetimibe</traditional_iupac>
  <cas_registry_number>163222-33-1</cas_registry_number>
  <smiles>O[C@@H](CC[C@@H]1[C@H](N(C1=O)C1=CC=C(F)C=C1)C1=CC=C(O)C=C1)C1=CC=C(F)C=C1</smiles>
  <inchi>InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1</inchi>
  <inchikey>OLNTVTPDXPETLC-XPWALMASSA-N</inchikey>
  <taxonomy>
    <kingdom/>
    <super_class/>
    <class/>
    <sub_class/>
    <direct_parent/>
    <alternate_parents/>
    <substituents/>
    <molecular_framework/>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Ezetimibe Action Pathway</name>
      <smpdb_id>SMP0125259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ezetimibe Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143403</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>4.56</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.46e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>409.4252</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>409.148949953</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H](CC[C@@H]1[C@H](N(C1=O)C1=CC=C(F)C=C1)C1=CC=C(O)C=C1)C1=CC=C(F)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H21F2NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OLNTVTPDXPETLC-XPWALMASSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>108.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</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:0x00007f7278c93708&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00973</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>150311</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>132493</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>BE0000802</target_id>
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      <target_id>BE0001078</target_id>
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      <target_id>BE0000105</target_id>
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  </targets>
</compound>
