<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-20 16:10:32 UTC</creation_date>
  <update_date>2026-08-18 17:49:45 UTC</update_date>
  <accession/>
  <common_name>Sulfamethazine</common_name>
  <class>SmallMolecule</class>
  <description>Sulfamethazine is an organic compound with the formula C12H14N4O2S and an average molecular weight of 278.33 g/mol. Sulfamethazine belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. It functions as an inhibitor of the protein target dihydropteroate synthase (folP). Regarding health effects, the compound is associated with obesity (PMC11271401).

The compound has been found in or released from 34 recorded sources. These include healthcare, pharmaceuticals and veterinary products such as antibiotics, gynecologicals, and sulfonamides and trimethoprim. It is also present in aquatic systems and sediments, including seawater, groundwater, freshwater, and surface water, as well as drinking water and water supply sources such as bottled water, tap water, desalinated water, and drinking water. Other sources include wastewater, sanitation and biosolids, specifically unspecified wastewater, mine wastewater, industrial wastewater, and wastewater treatment effluent. Additionally, it is found in household cleaning and consumer products, including tobacco smoke filters, perfumes within detergents and soaps, and non electric simulated smoking devices. Recorded sources also include electrical and electronic equipment, such as electrodes, electric switches, antennas, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices, along with six more sectors. Exposure routes for sulfamethazine include oral, inhalation, and touch.</description>
  <categories/>
  <types>
    <type>PMT</type>
  </types>
  <synonyms>
    <synonym>4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide</synonym>
    <synonym>Sulfadimidine</synonym>
  </synonyms>
  <chemical_formula>C12H14N4O2S</chemical_formula>
  <average_molecular_weight>278.33</average_molecular_weight>
  <monisotopic_moleculate_weight>278.083746402</monisotopic_moleculate_weight>
  <iupac_name>4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide</iupac_name>
  <traditional_iupac>sulfamethazine</traditional_iupac>
  <cas_registry_number>57-68-1</cas_registry_number>
  <smiles>CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N1</smiles>
  <inchi>InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)</inchi>
  <inchikey>ASWVTGNCAZCNNR-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>Pyrimidines and pyrimidine derivatives</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>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>Pyrimidine</substituent>
      <substituent>Sulfonyl</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>pyrimidines</descriptor>
      <descriptor>sulfonamide</descriptor>
      <descriptor>sulfonamide antibiotic</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Sulfamethazine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sulfamethazine Predicted Metabolism Pathway</name>
      <smpdb_id>SMP0174728</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>0.65</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.30e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>6.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>278.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>278.083746402</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H14N4O2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ASWVTGNCAZCNNR-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>73.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.8</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:0x00007f727b13a2a0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01582</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>5327</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>5136</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>
