<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:27:47 UTC</creation_date>
  <update_date>2026-08-18 08:07:22 UTC</update_date>
  <accession/>
  <common_name>Phenazopyridine</common_name>
  <class>SmallMolecule</class>
  <description>Phenazopyridine is an organic compound with the chemical formula C11H11N5 and an average molecular weight of 213.24 g/mol. Phenazopyridine belongs to the aminopyridines and derivatives, a subclass of pyridines and derivatives within the organic compounds. It is further categorized under the superclass of organoheterocyclic compounds.

The compound is found in or released from 19 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used in urologicals. In the category of food, food processing, and cookware, it is associated with food preservation. It is also found in household items, specifically watch chains, and in household cleaning and consumer products, including soap detergents, perfumes within detergents and soaps, bleaching agents, cigar cigarettes, other smoking requisites, and one additional source. Furthermore, it is released from electrical and electronic equipment, including electric switches, antennas, coils, conductors or conductive bodies characterised by the conductive materials, electrically stimulated smoking devices, and five more sources.

Regarding its biological activity, phenazopyridine acts as an inhibitor of the sodium channel protein type 1 subunit alpha (SCN1A), which is its single recorded protein target. The recorded route of exposure for this compound is oral.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C11H11N5</chemical_formula>
  <average_molecular_weight>213.2385</average_molecular_weight>
  <monisotopic_moleculate_weight>213.101445377</monisotopic_moleculate_weight>
  <iupac_name>3-[(E)-2-phenyldiazen-1-yl]pyridine-2,6-diamine</iupac_name>
  <traditional_iupac>phenazopyridine</traditional_iupac>
  <cas_registry_number>94-78-0</cas_registry_number>
  <smiles>NC1=NC(N)=C(C=C1)\N=N\C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C11H11N5/c12-10-7-6-9(11(13)14-10)16-15-8-4-2-1-3-5-8/h1-7H,(H4,12,13,14)/b16-15+</inchi>
  <inchikey>QPFYXYFORQJZEC-FOCLMDBBSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Aminopyridines and derivatives</sub_class>
    <direct_parent>Aminopyridines and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Azo compounds</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Dihydropyridines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aminopyridine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azo compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Dihydropyridine</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyridine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Phenazopyridine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143768</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>2.69</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.02e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(E)-2-phenyldiazen-1-yl]pyridine-2,6-diamine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>213.2385</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>213.101445377</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(N)=C(C=C1)\N=N\C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H11N5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H11N5/c12-10-7-6-9(11(13)14-10)16-15-8-4-2-1-3-5-8/h1-7H,(H4,12,13,14)/b16-15+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QPFYXYFORQJZEC-FOCLMDBBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>89.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</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:0x00007f3bb3e01910&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01438</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4756</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4592</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>
