Glimepiride (CED0003186)

Record Information
Version1.0
Creation Date2016-05-22 04:28:15 UTC
Update Date2026-08-22 04:03:01 UTC
Accession NumberCHEM017573
Identification
Common NameGlimepiride
ClassSmall Molecule
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.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
1-((p-(2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl)phenyl)sulfonyl)-3-(trans-4-methylcyclohexyl)ureaChEBI
1-{[4-(2-{[(3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)carbonyl]amino}ethyl)phenyl]sulfonyl}-3-(trans-4-methylcyclohexyl)ureaChEBI
AmarylChEBI
GimepirideChEBI
GlimepiridaChEBI
GlimepiridumChEBI
1-((p-(2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl)phenyl)sulphonyl)-3-(trans-4-methylcyclohexyl)ureaGenerator
1-{[4-(2-{[(3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)carbonyl]amino}ethyl)phenyl]sulphonyl}-3-(trans-4-methylcyclohexyl)ureaGenerator
Chemical FormulaC24H34N4O5S
Average Molecular Mass490.620 g/mol
Monoisotopic Mass490.225 g/mol
CAS Registry Number93479-97-1
IUPAC Name3-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
Traditional Nameglimepiride
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
InChI IdentifierInChI=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 KeyWIGIZIANZCJQQY-RUCARUNLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Pyrroline carboxylic acid or derivatives
  • N-acyl urea
  • Ureide
  • Sulfonylurea
  • Dicarboximide
  • Pyrroline
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Carbonic acid derivative
  • Urea
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP3.03ALOGPS
logP4.76ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)2.23ChemAxon
pKa (Strongest Basic)-0.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area131.66 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity130.85 m³·mol⁻¹ChemAxon
Polarizability53.31 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0012290000-966a50af984de12b0ba8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2629000000-29b987358cc85159c5b8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052f-2930000000-37fde3d60af9b32825caNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0012290000-966a50af984de12b0ba8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2629000000-29b987358cc85159c5b8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0002190000-0aaefa2e07605da97f81Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0409000000-91b493608ac508427593Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-3911000000-78c0f40c965f78bfa591Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6x-0609600000-78d1eafeec0253910006Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-1901000000-b9852a723bfd8ea4ca66Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02vi-7900000000-f9c7acb1abe1893597e7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0h2r-1908700000-4fe360933ffe931da22bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fmi-1927000000-d9a3ae76a7506ed0cee4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0229-4900000000-dcfccdc01980e9b7b49eNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
8897.0Log mg/kg[5000:16000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
263Blood glucose lowering drugs, excl. insulinsHealthcare, pharmaceuticals & veterinary productsNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)142.775
Click to view 3D structureProstaglandin E receptor 4Q9TU16Canis lupus familiarisPredicted (SEA)9.26406
Aldo-keto reductase family 1 member C3 structureClick to view 3D structureAldo-keto reductase family 1 member C3P42330HumansPredicted (SEA)281.269
Aldo-keto reductase family 1 member C1 structureClick to view 3D structureAldo-keto reductase family 1 member C1Q04828HumansPredicted (SEA)125.726
Collagenase 3 structureClick to view 3D structureCollagenase 3P45452HumansPredicted (SEA)1670.64
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)1825.72
Thromboxane A2 receptor structureClick to view 3D structureThromboxane A2 receptorP21731HumansPredicted (SEA)770.396
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)2393.47
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)2045.1
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)2729.0
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)4920.69
Neutrophil collagenase structureClick to view 3D structureNeutrophil collagenaseP22894HumansPredicted (SEA)1670.02
Mucolipin-1 structureClick to view 3D structureMucolipin-1Q9GZU1HumansPredicted (SEA)102.917
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)6521.12
Matrix metalloproteinase-9 structureClick to view 3D structureMatrix metalloproteinase-9P14780HumansPredicted (SEA)2629.98
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)3108.05
Click to view 3D structureRAC-alpha serine/threonine-protein kinaseP31750MousePredicted (SEA)57.1413
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)2713.98
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)2521.77
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)1528.02
Apoptotic protease-activating factor 1 structureClick to view 3D structureApoptotic protease-activating factor 1O14727HumansPredicted (SEA)891.14
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)2058.96
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)1455.24
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)543.543
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)1672.9
Concentrations
Not Available
External Links
DrugBank IDDB00222
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGlimepiride
Chemspider IDNot Available
ChEBI ID5383
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11199230
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12369756
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12852703
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22469262
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23305037
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=8141820