<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:28:15 UTC</creation_date>
  <update_date>2026-08-22 04:03:01 UTC</update_date>
  <accession/>
  <common_name>Glimepiride</common_name>
  <class>SmallMolecule</class>
  <description>Glimepiride is an organic compound with the chemical formula C24H34N4O5S and an average molecular weight of 490.62 g/mol. Glimepiride belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds.

This compound is identified as a blood glucose lowering drug, excluding insulins, with a recorded oral exposure route. It interacts with four protein targets, acting as a blocker, inducer, or inhibitor of the ATP-sensitive inward rectifier potassium channel 1 (KCNJ1), the ATP-sensitive inward rectifier potassium channel 11 (KCNJ11), the ATP-binding cassette sub-family C member 8 (ABCC8), and the ATP-binding cassette sub-family C member 9 (ABCC9).

Glimepiride has been found in or released from 24 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is used in blood glucose lowering drugs. In the food, food processing, and cookware sector, it is associated with food preservation and the preparation of vinegar, wort, and wine or sparkling wine. It is also linked to household cleaning and consumer products, including bleaching agents, perfumes within detergents and soaps, cigar cigarettes, non-electric simulated smoking devices, and other smoking requisites. In building and construction, it is found in tents, canopies, and sunshades, awnings, or outside screens. Finally, it is recorded in electrical and electronic equipment, such as antennas, conductors or conductive bodies characterised by the conductive materials, electrodes, discharge lamps, and electrically stimulated smoking devices.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C24H34N4O5S</chemical_formula>
  <average_molecular_weight>490.62</average_molecular_weight>
  <monisotopic_moleculate_weight>490.224991385</monisotopic_moleculate_weight>
  <iupac_name>3-ethyl-4-methyl-2-oxo-N-(2-{4-[({[(1r,4r)-4-methylcyclohexyl]-C-hydroxycarbonimidoyl}amino)sulfonyl]phenyl}ethyl)-2,5-dihydro-1H-pyrrole-1-carboximidic acid</iupac_name>
  <traditional_iupac>glimepiride</traditional_iupac>
  <cas_registry_number>93479-97-1</cas_registry_number>
  <smiles>[H][C@]1(C)CC[C@@]([H])(CC1)N=C(O)NS(=O)(=O)C1=CC=C(CCN=C(O)N2CC(C)=C(CC)C2=O)C=C1</smiles>
  <inchi>InChI=1S/C24H34N4O5S/c1-4-21-17(3)15-28(22(21)29)24(31)25-14-13-18-7-11-20(12-8-18)34(32,33)27-23(30)26-19-9-5-16(2)6-10-19/h7-8,11-12,16,19H,4-6,9-10,13-15H2,1-3H3,(H,25,31)(H2,26,27,30)/t16-,19-</inchi>
  <inchikey>WIGIZIANZCJQQY-RUCARUNLSA-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>Aminosulfonyl compounds</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenesulfonyl compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Dicarboximides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl ureas</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonic acids and derivatives</alternative_parent>
      <alternative_parent>Pyrroline carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Sulfonylureas</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aminosulfonyl compound</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenesulfonamide</substituent>
      <substituent>Benzenesulfonyl group</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboximide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl urea</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>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Pyrroline</substituent>
      <substituent>Pyrroline carboxylic acid or derivatives</substituent>
      <substituent>Sulfonyl</substituent>
      <substituent>Sulfonylurea</substituent>
      <substituent>Urea</substituent>
      <substituent>Ureide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>N-acylurea</descriptor>
      <descriptor>N-sulfonylurea</descriptor>
      <descriptor>sulfonamide</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Glimepiride Action Pathway</name>
      <smpdb_id>SMP0124722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glimepiride Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142684</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>3.12</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.47e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-ethyl-4-methyl-2-oxo-N-(2-{4-[({[(1r,4r)-4-methylcyclohexyl]-C-hydroxycarbonimidoyl}amino)sulfonyl]phenyl}ethyl)-2,5-dihydro-1H-pyrrole-1-carboximidic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>490.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>490.224991385</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(C)CC[C@@]([H])(CC1)N=C(O)NS(=O)(=O)C1=CC=C(CCN=C(O)N2CC(C)=C(CC)C2=O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H34N4O5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H34N4O5S/c1-4-21-17(3)15-28(22(21)29)24(31)25-14-13-18-7-11-20(12-8-18)34(32,33)27-23(30)26-19-9-5-16(2)6-10-19/h7-8,11-12,16,19H,4-6,9-10,13-15H2,1-3H3,(H,25,31)(H2,26,27,30)/t16-,19-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WIGIZIANZCJQQY-RUCARUNLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>131.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>130.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</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:0x00007f3bf8601180&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00222</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>3476</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>3357</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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  </targets>
</compound>
