<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:23:36 UTC</creation_date>
  <update_date>2026-08-22 01:02:43 UTC</update_date>
  <accession/>
  <common_name>Glybenclamide</common_name>
  <class>SmallMolecule</class>
  <description>Glybenclamide is an organic compound with the formula C23H28ClN3O5S and an average molecular weight of 494.00 g/mol. Glybenclamide belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. It is recorded as being found in or released from 30 sources, including drinking water, ladders, and household cleaning and consumer products such as perfumes within detergents and soaps, ash trays, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices. Other sources include food, food processing and cookware—specifically food preservation, processing meats, fermentation processes for beer, the preparation of vinegar, and the preparation of wort—as well as electrical and electronic equipment including antennas, auxiliary devices, electric switches, conductive bodies characterised by the conductive materials, and cores yokes or armatures. Additionally, it is found in healthcare, pharmaceuticals and veterinary products as blood glucose lowering drugs, excluding insulins. The recorded exposure route is oral.

The compound interacts with nine protein targets, acting as an antagonist, inhibitor, or modulator of the ATP-binding cassette sub-family C member 9 (ABCC9), the bile salt export pump (ABCB11), the phospholipid-transporting ATPase ABCA1, the cystic fibrosis transmembrane conductance regulator (CFTR), and five other proteins. In terms of health effects, glybenclamide is used as a treatment for diabetes mellitus (PMC4285261), type 2 diabetes mellitus (PMC10904444), gestational diabetes (PMC5384842), and edema (PMC11832355). It further exhibits therapeutic effects on inflammation (PMC6329030) and hyperglycemia (PMC11127218).</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms>
    <synonym>5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide</synonym>
    <synonym>GLIBENCLAMIDE</synonym>
    <synonym>Glyburide</synonym>
  </synonyms>
  <chemical_formula>C23H28ClN3O5S</chemical_formula>
  <average_molecular_weight>494.004</average_molecular_weight>
  <monisotopic_moleculate_weight>493.143819418</monisotopic_moleculate_weight>
  <iupac_name>5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide</iupac_name>
  <traditional_iupac>glyburide</traditional_iupac>
  <cas_registry_number>10238-21-8</cas_registry_number>
  <smiles>COC1=C(C=C(Cl)C=C1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1</smiles>
  <inchi>InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)</inchi>
  <inchikey>ZNNLBTZKUZBEKO-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>Benzenesulfonamides</direct_parent>
    <alternate_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Aminosulfonyl compounds</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Benzenesulfonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Chlorobenzenes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonic acids and derivatives</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Sulfonylureas</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aminosulfonyl compound</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Benzenesulfonamide</substituent>
      <substituent>Benzenesulfonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Chlorobenzene</substituent>
      <substituent>Ether</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Organic 1,3-dipolar compound</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>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Sulfonyl</substituent>
      <substituent>Sulfonylurea</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>N-sulfonylurea</descriptor>
      <descriptor>monochlorobenzenes</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Glibenclamide Action Pathway</name>
      <smpdb_id>SMP0000460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glyburide Action Pathway</name>
      <smpdb_id>SMP0126298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glyburide Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143446</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>3.79</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.06e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>494.004</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>493.143819418</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=C(C=C(Cl)C=C1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C23H28ClN3O5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZNNLBTZKUZBEKO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</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:0x00007f7225e6c460&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01016</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>3488</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>3368</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
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  <chebi_id/>
  <biocyc_id/>
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  <wikipidia/>
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