<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-20 16:10:25 UTC</creation_date>
  <update_date>2026-08-18 15:54:35 UTC</update_date>
  <accession/>
  <common_name>Furosemide (Frusemide)</common_name>
  <class>SmallMolecule</class>
  <description>Furosemide (Frusemide) belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. This benzenoid compound has the formula C12H11ClN2O5S and an average molecular weight of 330.74 g/mol. It functions as a biological diuretic (PMC10884053, PMC7112026). Its recorded protein targets include the G-protein coupled receptor 35 (GPR35), Carbonic anhydrase 2 (CA2), and the Solute carrier family 12 member 1 (SLC12A1), for which it acts as an agonist/inhibitor.

Furosemide is used as a treatment for high blood pressure (PMC10698095), hypertension (PMC13344627), hypercalcemia (PMC1492602), and congestive heart failure (PMC10193417, PMC1492602). Exposure routes for the compound include oral, intravenous, intravascular, subcutaneous, intramuscular, and topical administration. It has been found in or released from 66 recorded sources across multiple sectors. These include healthcare, pharmaceuticals and veterinary products, such as gynecologicals and diuretics; food, food processing and cookware, including food preservation and the preparation of malt, vinegar, beer fermentation processes, and wine or sparkling wine; household items such as key rings, coins, and credit card holders; building and construction materials including roofs, ladders, floors, fencing, and ceilings; household cleaning and consumer products such as bleaching agents, ash trays, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices; and electrical and electronic equipment, including amplifiers, antennas, coils, adjustable resistors, auxiliary devices, and 27 additional sources.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>4-chloro-2-{[(furan-2-yl)methyl]amino}-5-sulfamoylbenzoic acid</synonym>
    <synonym>Frusemide</synonym>
    <synonym>Furosemide</synonym>
    <synonym>furosemide</synonym>
  </synonyms>
  <chemical_formula>C12H11ClN2O5S</chemical_formula>
  <average_molecular_weight>330.744</average_molecular_weight>
  <monisotopic_moleculate_weight>330.007719869</monisotopic_moleculate_weight>
  <iupac_name>4-chloro-2-{[(furan-2-yl)methyl]amino}-5-sulfamoylbenzoic acid</iupac_name>
  <traditional_iupac>furosemide</traditional_iupac>
  <cas_registry_number>54-31-9</cas_registry_number>
  <smiles>NS(=O)(=O)C1=C(Cl)C=C(NCC2=CC=CO2)C(=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C12H11ClN2O5S/c13-9-5-10(15-6-7-2-1-3-20-7)8(12(16)17)4-11(9)21(14,18)19/h1-5,15H,6H2,(H,16,17)(H2,14,18,19)</inchi>
  <inchikey>ZZUFCTLCJUWOSV-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>4-halobenzoic acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminobenzoic acids</alternative_parent>
      <alternative_parent>Aminosulfonyl compounds</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Benzenesulfonyl compounds</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Chlorobenzenes</alternative_parent>
      <alternative_parent>Furans</alternative_parent>
      <alternative_parent>Halobenzoic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonamides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Phenylalkylamines</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>4-halobenzoic acid</substituent>
      <substituent>4-halobenzoic acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzenesulfonamide</substituent>
      <substituent>Aminobenzoic acid</substituent>
      <substituent>Aminobenzoic acid or derivatives</substituent>
      <substituent>Aminosulfonyl compound</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Benzenesulfonyl group</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Chlorobenzene</substituent>
      <substituent>Furan</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Halobenzoic acid</substituent>
      <substituent>Halobenzoic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid amide</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phenylalkylamine</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Sulfonyl</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>chlorobenzoic acid</descriptor>
      <descriptor>furans</descriptor>
      <descriptor>sulfonamide</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Furosemide Action Pathway</name>
      <smpdb_id>SMP0000115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Furosemide Diuretic Action Pathway</name>
      <smpdb_id>SMP0122712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Furosemide Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Furosemide Predicted Metabolism Pathway</name>
      <smpdb_id>SMP0174583</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>1.75</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.18e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-chloro-2-{[(furan-2-yl)methyl]amino}-5-sulfamoylbenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>330.744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>330.007719869</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NS(=O)(=O)C1=C(Cl)C=C(NCC2=CC=CO2)C(=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H11ClN2O5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H11ClN2O5S/c13-9-5-10(15-6-7-2-1-3-20-7)8(12(16)17)4-11(9)21(14,18)19/h1-5,15H,6H2,(H,16,17)(H2,14,18,19)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZZUFCTLCJUWOSV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>122.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>77.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</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:0x00007f72263c3cb0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00695</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>3440</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>3322</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>
