<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 05:01:58 UTC</creation_date>
  <update_date>2026-08-20 06:25:39 UTC</update_date>
  <accession/>
  <common_name>Cilostazol</common_name>
  <class>SmallMolecule</class>
  <description>Cilostazol is an organic compound with the formula C20H27N5O2 and an average molecular weight of 369.46 g/mol. Cilostazol belongs to the quinolones and derivatives, a subclass of quinolines and derivatives within the organic compounds. It functions as an inhibitor of cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A (PDE3A) and serves as a biological antioxidant (PMC9368651).

The compound is used as an antithrombotic agent within healthcare, pharmaceuticals, and veterinary products. Its health effects include treatment for kidney disease (PMC9368651), cerebrovascular disease (PMC9368651), and coronary artery disease (PMC9368651). Additionally, it has a therapeutic effect on stroke (PMC3148418).

Cilostazol is found in or released from eight recorded sources. These include electrical and electronic equipment, such as discharge tubes with liquid pool cathodes, antennas, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. It is also associated with household cleaning and consumer products, specifically tobacco smoke filters, cigar cigarettes, and other smoking requisites. Recorded exposure routes for the compound include oral and conjunctival pathways.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C20H27N5O2</chemical_formula>
  <average_molecular_weight>369.4607</average_molecular_weight>
  <monisotopic_moleculate_weight>369.216475133</monisotopic_moleculate_weight>
  <iupac_name>6-[4-(1-cyclohexyl-1H-1,2,3,4-tetrazol-5-yl)butoxy]-1,2,3,4-tetrahydroquinolin-2-one</iupac_name>
  <traditional_iupac>cilostazol</traditional_iupac>
  <cas_registry_number>73963-72-1</cas_registry_number>
  <smiles>O=C1CCC2=C(N1)C=CC(OCCCCC1=NN=NN1C1CCCCC1)=C2</smiles>
  <inchi>InChI=1S/C20H27N5O2/c26-20-12-9-15-14-17(10-11-18(15)21-20)27-13-5-4-8-19-22-23-24-25(19)16-6-2-1-3-7-16/h10-11,14,16H,1-9,12-13H2,(H,21,26)</inchi>
  <inchikey>RRGUKTPIGVIEKM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Quinolines and derivatives</class>
    <sub_class>Quinolones and derivatives</sub_class>
    <direct_parent>Hydroquinolones</direct_parent>
    <alternate_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroquinolines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tetrazoles</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</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>Secondary carboxylic acid amide</substituent>
      <substituent>Tetrahydroquinoline</substituent>
      <substituent>Tetrahydroquinolone</substituent>
      <substituent>Tetrazole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>lactam</descriptor>
      <descriptor>tetrazoles</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Cilostazol Action Pathway</name>
      <smpdb_id>SMP0000263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cilostazol Action Pathway (new)</name>
      <smpdb_id>SMP0122708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cilostazol Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cilostazol Predicted Metabolism Pathway</name>
      <smpdb_id>SMP0174698</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>3.31</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.24e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-[4-(1-cyclohexyl-1H-1,2,3,4-tetrazol-5-yl)butoxy]-1,2,3,4-tetrahydroquinolin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>369.4607</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>369.216475133</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O=C1CCC2=C(N1)C=CC(OCCCCC1=NN=NN1C1CCCCC1)=C2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H27N5O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H27N5O2/c26-20-12-9-15-14-17(10-11-18(15)21-20)27-13-5-4-8-19-22-23-24-25(19)16-6-2-1-3-7-16/h10-11,14,16H,1-9,12-13H2,(H,21,26)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RRGUKTPIGVIEKM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>81.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>117.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</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:0x00007f7261f552a0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01166</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>2754</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>2652</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>BE0000436</target_id>
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  </targets>
</compound>
