<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:30:32 UTC</creation_date>
  <update_date>2026-08-22 23:36:29 UTC</update_date>
  <accession/>
  <common_name>Pyrazinamide</common_name>
  <class>SmallMolecule</class>
  <description>Pyrazinamide (C5H5N3O) is an organic compound with an average molecular weight of 123.11 g/mol. Pyrazinamide belongs to the pyrazines, a subclass of diazines within the organic compounds. This substance is recorded as being found in or released from 36 different sources, including electrical and electronic equipment such as antennas, amplifiers, adjustable resistors, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials, among 13 others. It is also found in building and construction materials, including stairs and ramps, ceilings, floors, roofs, and sunshades awnings or outside screens, as well as two additional sources. Other sources include household cleaning and consumer products such as soap detergents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and two others. Additionally, it is associated with food, food processing and cookware, specifically the preparation of malt, food preservation, and the processing of meats. Within healthcare, pharmaceuticals, and veterinary products, it is used in drugs for the treatment of tuberculosis. The recorded route of exposure is oral.

Pyrazinamide acts on two recorded protein targets, serving as an inhibitor of enoyl-[acyl-carrier-protein] reductase [NADH] (inhA) and the probable fatty acid synthase Fas (fatty acid synthetase) (fas). Regarding its health effects, the compound is used as a treatment for tuberculosis (PMC10819319, PMC10963064, PMC11025081).</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms>
    <synonym>pyrazine-2-carboxamide</synonym>
  </synonyms>
  <chemical_formula>C5H5N3O</chemical_formula>
  <average_molecular_weight>123.1127</average_molecular_weight>
  <monisotopic_moleculate_weight>123.043261797</monisotopic_moleculate_weight>
  <iupac_name>pyrazine-2-carboxamide</iupac_name>
  <traditional_iupac>pyrazinamide</traditional_iupac>
  <cas_registry_number>98-96-4</cas_registry_number>
  <smiles>NC(=O)C1=NC=CN=C1</smiles>
  <inchi>InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)</inchi>
  <inchikey>IPEHBUMCGVEMRF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrazines</sub_class>
    <direct_parent>Pyrazines</direct_parent>
    <alternate_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrazine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>a carboxamide</descriptor>
      <descriptor>monocarboxylic acid amide</descriptor>
      <descriptor>pyrazines</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Pyrazinamide Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrazinamide Action Pathway</name>
      <smpdb_id>SMP0718082</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>9.37e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>pyrazine-2-carboxamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>123.1127</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>123.043261797</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)C1=NC=CN=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H5N3O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IPEHBUMCGVEMRF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>68.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</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:0x00007f722625a798&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00339</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>1046</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>1017</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>
