<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:46:24 UTC</creation_date>
  <update_date>2026-08-18 09:04:21 UTC</update_date>
  <accession/>
  <common_name>Sulfamerazine</common_name>
  <class>SmallMolecule</class>
  <description>Sulfamerazine is an organic compound with the chemical formula C11H12N4O2S and an average molecular weight of 264.30 g/mol. Sulfamerazine belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. In terms of biological activity, it acts as an inhibitor of the protein target dihydropteroate synthase (folP).

The compound is found in or released from 11 recorded sources across various sectors. Within healthcare, pharmaceuticals, and veterinary products, it is associated with antibiotics, chemotherapy, gynecologicals, and sulfonamides and trimethoprim. In the category of household cleaning and consumer products, it is linked to perfumes within detergents and soaps, tobacco smoke filters, and non-electric simulated smoking devices. It is also found in electrical and electronic equipment, specifically electrically stimulated smoking devices and electric switches. Additionally, it is recorded in drinking water and water supply, as well as in food preservation within the food, food processing, and cookware sector. Recorded routes of exposure for this compound include inhalation and oral administration.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C11H12N4O2S</chemical_formula>
  <average_molecular_weight>264.304</average_molecular_weight>
  <monisotopic_moleculate_weight>264.068096338</monisotopic_moleculate_weight>
  <iupac_name>4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide</iupac_name>
  <traditional_iupac>sulfamerazine</traditional_iupac>
  <cas_registry_number>127-79-7</cas_registry_number>
  <smiles>CC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C1</smiles>
  <inchi>InChI=1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)</inchi>
  <inchikey>QPPBRPIAZZHUNT-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>Sulfamerazine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sulfamerazine Predicted Metabolism Pathway</name>
      <smpdb_id>SMP0174727</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>0.52</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.04e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.52</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>2.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>264.304</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>264.068096338</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H12N4O2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QPPBRPIAZZHUNT-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>68.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.51</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:0x00007f7226357b28&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01581</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>5325</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>5134</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>
