<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:46:28 UTC</creation_date>
  <update_date>2026-08-25 07:47:36 UTC</update_date>
  <accession/>
  <common_name>Sulfamethizole</common_name>
  <class>SmallMolecule</class>
  <description>Sulfamethizole is an organic compound with the chemical formula C9H10N4O2S2 and an average molecular weight of 270.33 g/mol. Sulfamethizole belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. In terms of biological activity, it is recorded as an inhibitor of the protein target dihydropteroate synthase (folP).

The compound is found in or released from 23 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is associated with antiinfectives, chemotherapy, gynecologicals, irrigating solutions, and sulfonamides and trimethoprim. It is also linked to food, food processing, and cookware, specifically in meat processing, food preservation, and the preparation of wort. Other recorded sources include household cleaning and consumer products, such as soap detergents, perfumes within detergents and soaps, and tobacco smoke filters. Additionally, it is found in building and construction materials, specifically roofs, as well as electrical and electronic equipment, including communication cables or conductors, antennas, coils, cores yokes or armatures, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for this compound include inhalation and oral ingestion.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>sulfamethiozole</synonym>
  </synonyms>
  <chemical_formula>C9H10N4O2S2</chemical_formula>
  <average_molecular_weight>270.331</average_molecular_weight>
  <monisotopic_moleculate_weight>270.024516964</monisotopic_moleculate_weight>
  <iupac_name>4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide</iupac_name>
  <traditional_iupac>sulfamethizole</traditional_iupac>
  <cas_registry_number>144-82-1</cas_registry_number>
  <smiles>CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1</smiles>
  <inchi>InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)</inchi>
  <inchikey>VACCAVUAMIDAGB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzenesulfonamides</sub_class>
    <direct_parent>Aminobenzenesulfonamides</direct_parent>
    <alternate_parents>
      <alternative_parent>Aminosulfonyl compounds</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenesulfonyl compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonamides</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Thiadiazoles</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aminobenzenesulfonamide</substituent>
      <substituent>Aminosulfonyl compound</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenesulfonyl group</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid amide</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Sulfonyl</substituent>
      <substituent>Thiadiazole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>sulfonamide</descriptor>
      <descriptor>sulfonamide antibiotic</descriptor>
      <descriptor>thiadiazoles</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Sulfamethizole Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143025</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.11e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>6.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>270.331</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>270.024516964</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10N4O2S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VACCAVUAMIDAGB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>66.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.26</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>-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/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bf821c768&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00576</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>5328</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>5137</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>
