<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:29:21 UTC</creation_date>
  <update_date>2026-08-20 05:19:40 UTC</update_date>
  <accession/>
  <common_name>Prasugrel</common_name>
  <class>SmallMolecule</class>
  <description>Prasugrel is an organic compound with the formula C20H20FNO3S and an average molecular weight of 373.44 g/mol. Prasugrel belongs to the thienopyridines, a class of organoheterocyclic compounds within the organic compounds. It acts as an antagonist of the P2Y purinoceptor 12 (P2RY12) protein target.

The compound is found in or released from two recorded sources: amplifiers within electrical and electronic equipment and antithrombotic agents within healthcare, pharmaceuticals, and veterinary products. The recorded route of exposure for this compound is oral.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C20H20FNO3S</chemical_formula>
  <average_molecular_weight>373.441</average_molecular_weight>
  <monisotopic_moleculate_weight>373.114792406</monisotopic_moleculate_weight>
  <iupac_name>5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4H,5H,6H,7H-thieno[3,2-c]pyridin-2-yl acetate</iupac_name>
  <traditional_iupac>prasugrel</traditional_iupac>
  <cas_registry_number>150322-43-3</cas_registry_number>
  <smiles>CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C2CC2)C2=CC=CC=C2F)S1</smiles>
  <inchi>InChI=1S/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3</inchi>
  <inchikey>DTGLZDAWLRGWQN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Thienopyridines</class>
    <sub_class/>
    <direct_parent>Thienopyridines</direct_parent>
    <alternate_parents>
      <alternative_parent>2,3,5-trisubstituted thiophenes</alternative_parent>
      <alternative_parent>Alpha-amino ketones</alternative_parent>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aryl fluorides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Fluorobenzenes</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organofluorides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridines and derivatives</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>2,3,5-trisubstituted thiophene</substituent>
      <substituent>Alpha-aminoketone</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Aryl fluoride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Fluorobenzene</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organofluoride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
      <substituent>Thienopyridine</substituent>
      <substituent>Thiophene</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>acetate ester</descriptor>
      <descriptor>cyclopropanes</descriptor>
      <descriptor>ketone</descriptor>
      <descriptor>monofluorobenzenes</descriptor>
      <descriptor>tertiary amino compound</descriptor>
      <descriptor>thienopyridine</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Prasugrel Action Pathway</name>
      <smpdb_id>SMP0126463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Prasugrel Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0144010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Prasugrel Predicted Metabolism Pathway</name>
      <smpdb_id>SMP0174722</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>4.31</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.37e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4H,5H,6H,7H-thieno[3,2-c]pyridin-2-yl acetate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>373.441</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>373.114792406</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C2CC2)C2=CC=CC=C2F)S1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H20FNO3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DTGLZDAWLRGWQN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>46.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.7</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>0</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:0x00007f3bafdb8700&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB06209</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>6918456</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>5293653</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>
      <target_id>BE0000110</target_id>
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  </targets>
</compound>
