<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 06:58:55 UTC</creation_date>
  <update_date>2026-08-20 03:09:48 UTC</update_date>
  <accession/>
  <common_name>Prazosin</common_name>
  <class>SmallMolecule</class>
  <description>Prazosin is an organic compound with the chemical formula C19H21N5O4 and an average molecular weight of 383.40 g/mol. Prazosin belongs to the piperazines, a subclass of diazinanes within the organic compounds.

This compound is associated with 14 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used as an antihypertensive. It is also found in food preservation and various household cleaning and consumer products, including tobacco smoke filters, perfumes within detergents and soaps, non electric simulated smoking devices, cigar cigarettes, and other smoking requisites. Additionally, it is released from electrical and electronic equipment, specifically electrodes, antennas, coils, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. The recorded exposure route for this substance is oral.

At the molecular level, Prazosin interacts with six recorded protein targets. It acts as an antagonist, binder, or inhibitor of the Alpha-1A adrenergic receptor (ADRA1A), the Alpha-1B adrenergic receptor (ADRA1B), and the Alpha-1D adrenergic receptor (ADRA1D). Furthermore, it targets the voltage-gated inwardly rectifying potassium channel KCNH2 and two other proteins.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C19H21N5O4</chemical_formula>
  <average_molecular_weight>383.4011</average_molecular_weight>
  <monisotopic_moleculate_weight>383.159354185</monisotopic_moleculate_weight>
  <iupac_name>2-[4-(furan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine</iupac_name>
  <traditional_iupac>prazosin</traditional_iupac>
  <cas_registry_number>19216-56-9</cas_registry_number>
  <smiles>COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1=CC=CO1</smiles>
  <inchi>InChI=1S/C19H21N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22)</inchi>
  <inchikey>IENZQIKPVFGBNW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazinanes</class>
    <sub_class>Piperazines</sub_class>
    <direct_parent>N-arylpiperazines</direct_parent>
    <alternate_parents>
      <alternative_parent>2-heteroaryl carboxamides</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Dialkylarylamines</alternative_parent>
      <alternative_parent>Furoic acid and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Quinazolinamines</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>2-heteroaryl carboxamide</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkylarylamine</substituent>
      <substituent>Diazanaphthalene</substituent>
      <substituent>Ether</substituent>
      <substituent>Furan</substituent>
      <substituent>Furoic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>N-arylpiperazine</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>Oxacycle</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Quinazolinamine</substituent>
      <substituent>Quinazoline</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>aromatic ether</descriptor>
      <descriptor>furans</descriptor>
      <descriptor>monocarboxylic acid amide</descriptor>
      <descriptor>piperazines</descriptor>
      <descriptor>quinazolines</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Prazosin Action Pathway</name>
      <smpdb_id>SMP0125086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Prazosin Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Prazosin Predicted Metabolism Pathway</name>
      <smpdb_id>SMP0174674</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>1.65</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.93e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>7.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[4-(furan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>383.4011</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>383.159354185</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1=CC=CO1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H21N5O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H21N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IENZQIKPVFGBNW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>106.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>104.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</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/>
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  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bd0044d00&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00457</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4893</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4724</chemspider_id>
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  <wikipidia/>
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