Glimepiride (CHEM017573)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:28:15 UTC
Update Date2016-11-09 01:15:37 UTC
Accession NumberCHEM017573
Identification
Common NameGlimepiride
ClassSmall Molecule
DescriptionFirst introduced in 1995, glimepiride is a member of the second-generation sulfonylurea (SU) drug class used for the management of type 2 diabetes mellitus (T2DM) to improve glycemic control. Type 2 diabetes is a metabolic disorder with increasing prevalences worldwide; it is characterized by insulin resistance in accordance with progressive β cell failure and long-term microvascular and macrovascular complications that lead to co-morbidities and mortalities. Sulfonylureas are one of the insulin secretagogues widely used for the management of type 2 diabetes to lower blood glucose levels. The main effect of SUs is thought to be effective when residual pancreatic β-cells are present, as they work by stimulating the release of insulin from the pancreatic beta cells and they are also thought to exert extra-pancreatic effects, such as increasing the insulin-mediated peripheral glucose uptake. Glimepiride works by stimulating the secretion of insulin granules from pancreatic islet beta cells by blocking ATP-sensitive potassium channels (KATP channels) and causing depolarization of the beta cells. Compared to , another second SU drug, glimepiride has a longer duration of action. It is sometimes classified as a third-generation SU because it has larger substitutions than other second-generation SUs. Compared to other SUs, glimepiride was associated with a lower risk of developing hypoglycemia and weight gain in clinical trials as well as fewer cardiovascular effects than other SUs due to minimal effects on ischemic preconditioning of cardiac myocytes. It is effective in reducing fasting plasma glucose, postprandial glucose, and glycosylated hemoglobin levels and is considered to be a useful, cost-effective treatment option for managing type 2 diabetes mellitus. Glimepiride was approved by the Food and Drug Administration (FDA) in the United States in 1995 for the treatment of T2DM. It is commonly marketed under the brand name Glimepiride as oral tablets and is typically administered once daily.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-0012290000-966a50af984de12b0ba8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-2629000000-29b987358cc85159c5b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-052f-2930000000-37fde3d60af9b32825caSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0012290000-966a50af984de12b0ba8Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-2629000000-29b987358cc85159c5b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0002190000-0aaefa2e07605da97f81Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0409000000-91b493608ac508427593Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-3911000000-78c0f40c965f78bfa591Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6x-0609600000-78d1eafeec0253910006Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-1901000000-b9852a723bfd8ea4ca66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02vi-7900000000-f9c7acb1abe1893597e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0h2r-1908700000-4fe360933ffe931da22bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fmi-1927000000-d9a3ae76a7506ed0cee4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0229-4900000000-dcfccdc01980e9b7b49eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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