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Identification
NameGlimepiride
Accession NumberDB00222  (APRD00381)
TypeSmall Molecule
GroupsApproved
Description

Glimepiride is the first III generation sulphonyl urea it is a very potent sulphonyl urea with long duration of action.

Structure
Thumb
Synonyms
SynonymLanguageCode
AmarylNot AvailableNot Available
GlimepiridaSpanishINN
GlimépirideFrenchINN
GlimepiridumLatinINN
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amaryltablet1 mgoralSanofi Aventis U.S. Llc2009-06-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Amaryltablet2 mgoralSanofi Aventis U.S. Llc2009-06-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Amaryltablet4 mgoralSanofi Aventis U.S. Llc2009-06-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Amaryltablet1 mgoralSanofi Aventis Canada IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Amaryltablet2 mgoralSanofi Aventis Canada IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Amaryltablet4 mgoralSanofi Aventis Canada IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Glimepiridetablet1 mgoralTeva Pharmaceuticals USA Inc2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralTeva Pharmaceuticals USA Inc2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralTeva Pharmaceuticals USA Inc2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralMylan Pharmaceuticals Inc.2006-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralMylan Pharmaceuticals Inc.2006-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralMylan Pharmaceuticals Inc.2006-03-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralQualitest Pharmaceuticals2010-10-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralQualitest Pharmaceuticals2010-10-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralQualitest Pharmaceuticals2010-10-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralBlenheim Pharmacal, Inc.2013-10-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralAccord Healthcare Inc2007-08-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralAccord Healthcare Inc2007-08-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralAccord Healthcare Inc2007-08-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralRebel Distributors Corp2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralRebel Distributors Corp2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralRebel Distributors Corp2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralAidarex Pharmaceuticals LLC2013-06-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralAidarex Pharmaceuticals LLC2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralLake Erie Medical DBA Quality Care Products LLC2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralSTAT Rx USA LLC2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralSTAT Rx USA LLC2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralMicro Labs Limited2013-06-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralMicro Labs Limited2013-06-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet3 mgoralMicro Labs Limited2013-06-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralMicro Labs Limited2013-06-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet6 mgoralMicro Labs Limited2013-06-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet8 mgoralMicro Labs Limited2013-06-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralPd Rx Pharmaceuticals, Inc.2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralPd Rx Pharmaceuticals, Inc.2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralPd Rx Pharmaceuticals, Inc.2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralPerrigo New York Inc2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralPerrigo New York Inc2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralPerrigo New York Inc2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralUnit Dose Services2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralUnit Dose Services2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralUnit Dose Services2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralUDL Laboratories, Inc.2010-11-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralUDL Laboratories, Inc.2010-11-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralNorthwind Pharmaceuticals2014-12-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralREMEDYREPACK INC.2013-11-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralREMEDYREPACK INC.2013-05-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralREMEDYREPACK INC.2013-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralREMEDYREPACK INC.2013-11-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralInternational Labs, Inc.2009-02-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralInternational Labs, Inc.2009-02-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralInternational Labs, Inc.2009-02-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralPhysicians Total Care, Inc.2005-10-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralPhysicians Total Care, Inc.2005-10-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralPhysicians Total Care, Inc.2005-10-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralDr. Reddy's Laboratories Limited2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralDr. Reddy's Laboratories Limited2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralDr. Reddy's Laboratories Limited2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralCardinal Health2007-08-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralCardinal Health2007-08-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralCardinal Health2010-11-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralClinical Solutions Wholesale2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralClinical Solutions Wholesale2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralSt Marys Medical Park Pharmacy2014-05-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralSt Marys Medical Park Pharmacy2013-05-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralSt Marys Medical Park Pharmacy2013-05-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralCarlsbad Technology, Inc.2010-02-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralCarlsbad Technology, Inc.2010-02-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralCarlsbad Technology, Inc.2010-02-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralbryant ranch prepack2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralbryant ranch prepack2005-10-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralAurobindo Pharma Limited2012-06-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralAurobindo Pharma Limited2012-06-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralAurobindo Pharma Limited2012-06-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralMed Vantx, Inc.2012-04-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralBlue Point Laboratories2014-02-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralBlue Point Laboratories2014-02-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralBlue Point Laboratories2014-02-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralAmerican Health Packaging2009-05-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralAmerican Health Packaging2009-05-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralAmerican Health Packaging2014-07-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet1 mgoralVirtus Pharmaceuticals LLC2013-12-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet2 mgoralVirtus Pharmaceuticals LLC2013-12-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glimepiridetablet4 mgoralVirtus Pharmaceuticals LLC2013-12-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
GLIMPIDRanbaxy Laboratories
GLIMYDr.Reddy's Labs
Brand mixtures
Brand NameIngredients
Avandarylglimepiride + rosiglitazone maleate
DuetactGlimepiride + Pioglitazone
SaltsNot Available
Categories
CAS number93479-97-1
WeightAverage: 490.616
Monoisotopic: 490.224990908
Chemical FormulaC24H34N4O5S
InChI KeyWIGIZIANZCJQQY-UHFFFAOYSA-N
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)
IUPAC Name
3-ethyl-4-methyl-N-{2-[4-({[(4-methylcyclohexyl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide
SMILES
CCC1=C(C)CN(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC2CCC(C)CC2)C1=O
Taxonomy
DescriptionThis compound 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
  • Phenethylamine
  • Pyrroline carboxylic acid or derivatives
  • Ureide
  • Sulfonylurea
  • Cyclohexylamine
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Pyrroline
  • Urea
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor concomitant use with insulin for the treatment of noninsulin-dependent (type 2) diabetes mellitus.
PharmacodynamicsGlimepiride, like glyburide and glipizide, is a "second-generation" sulfonylurea agents. Glimepiride is used with diet to lower blood glucose by increasing the secretion of insulin from pancreas and increasing the sensitivity of peripheral tissues to insulin.
Mechanism of actionThe mechanism of action of glimepiride in lowering blood glucose appears to be dependent on stimulating the release of insulin from functioning pancreatic beta cells, and increasing sensitivity of peripheral tissues to insulin. Glimepiride likely binds to ATP-sensitive potassium channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Membrane depolarization stimulates calcium ion influx through voltage-sensitive calcium channels. This increase in intracellular calcium ion concentration induces the secretion of insulin.
AbsorptionCompletely (100%) absorbed following oral administration.
Volume of distribution
  • 21.8 ± 13.9 L [Volunteers]
  • 19.8 ± 12.7 L [Patients with Type 2 diabetes, Single Dose]
  • 37.1 ± 18.2 L [Patients with Type 2 diabetes, Multiple Dose]
Protein bindingOver 99.5% bound to plasma protein.
Metabolism

Hepatic. Following either an intravenous or oral dose, glimepiride is completely metabolized by oxidative biotransformation to a major metabolite, cyclohexyl hydroxymethyl derivative (M1), via the hepatic cytochrome P450 II C9 subsystem. M1 is further metabolized to the carboxyl derivative (M2) by one or several cytosolic enzymes. M1, but not M2, possessed approximately one third of the pharmacologic activity of its parent in an animal model. However, whether the glucose-lowering effect of M1 is clinically significant is not clear.

SubstrateEnzymesProduct
Glimepiride
Cyclohexyl hydroxymethyl glimepirideDetails
Cyclohexyl hydroxymethyl glimepiride
Cyclohexyl carboxyl glimepirideDetails
Route of eliminationNot Available
Half lifeApproximately 5 hours following single dose.
Clearance
  • 52.1 +/- 16.0 mL/min [Normal subjects with single oral dose]
  • 48.5 +/- 29.3 mL/min [Patients with Type 2 diabetes, with single oral dose]
  • 52.7 +/- 40.3 mL/min [Patients with Type 2 diabetes, with multiple oral dose]
  • 47.8 mL/min [healthy after intravenous (IV) dosing]
ToxicitySevere hypoglycemic reactions with coma, seizure, or other neurological impairment.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.986
Blood Brain Barrier+0.7322
Caco-2 permeable-0.6809
P-glycoprotein substrateSubstrate0.7501
P-glycoprotein inhibitor INon-inhibitor0.6556
P-glycoprotein inhibitor IIInhibitor0.6124
Renal organic cation transporterNon-inhibitor0.8241
CYP450 2C9 substrateSubstrate0.5661
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5978
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateInhibitor0.8949
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8599
Ames testNon AMES toxic0.6392
CarcinogenicityNon-carcinogens0.7301
BiodegradationNot ready biodegradable0.68
Rat acute toxicity2.4158 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7714
hERG inhibition (predictor II)Non-inhibitor0.8263
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • Accord healthcare inc
  • Carlsbad technology inc
  • Corepharma llc
  • Dr reddys laboratories ltd
  • Genpharm inc
  • Invagen pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Ranbaxy laboratories ltd
  • Teva pharmaceuticals usa inc
  • Vintage pharmaceuticals llc
  • Watson laboratories inc
  • Watson laboratories inc florida
Packagers
Dosage forms
FormRouteStrength
Tabletoral1 mg
Tabletoral2 mg
Tabletoral3 mg
Tabletoral4 mg
Tabletoral6 mg
Tabletoral8 mg
Prices
Unit descriptionCostUnit
Amaryl 4 mg tablet2.11USD tablet
Amaryl 2 mg tablet1.25USD tablet
Glimepiride 4 mg tablet1.25USD tablet
Amaryl 1 mg tablet0.88USD tablet
Glimepiride 2 mg tablet0.67USD tablet
Glimepiride 1 mg tablet0.42USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point207 °CNot Available
water solubilityInsolubleNot Available
logP3.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0384 mg/mLALOGPS
logP2.82ALOGPS
logP3.12ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.32ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area124.68 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.8 m3·mol-1ChemAxon
Polarizability53.86 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Suresh Kadam, Venkatasubramanian Tarur, Sanjay Naik, Sachin Gavhane, “Process for preparation of substantially pure glimepiride.” U.S. Patent US20070082943, issued April 12, 2007.

US20070082943
General ReferenceNot Available
External Links
ATC CodesA10BB12
AHFS Codes
  • 68:20.20
PDB EntriesNot Available
FDA labelDownload (176 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
CyclosporineThe sulfonylurea, glimepiride, may increase the effect of cyclosporine.
GemfibrozilGemfibrozil increases the effect and toxicity of rosiglitazone/pioglitazone
GlucosaminePossible hyperglycemia
KetoconazoleKetoconazole increases the effect of rosiglitazone
RifampicinRifampin may decrease the effect of sulfonylurea, glimepiride.
Somatropin recombinantSomatropin may antagonize the hypoglycemic effect of glimepiride. Monitor for changes in fasting and postprandial blood sugars.
TolbutamideTolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Glimepiride. Consider alternate therapy or monitor for changes in Glimepiride therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
Food Interactions
  • Avoid alcohol.
  • Even though food reduces product absorption, the manufacturer recommends taking the product with the first meal of the day.

Targets

1. ATP-sensitive inward rectifier potassium channel 11

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
ATP-sensitive inward rectifier potassium channel 11 Q14654 Details

References:

  1. Song DK, Ashcroft FM: Glimepiride block of cloned beta-cell, cardiac and smooth muscle K(ATP) channels. Br J Pharmacol. 2001 May;133(1):193-9. Pubmed
  2. Lawrence CL, Rainbow RD, Davies NW, Standen NB: Effect of metabolic inhibition on glimepiride block of native and cloned cardiac sarcolemmal K(ATP) channels. Br J Pharmacol. 2002 Jul;136(5):746-52. Pubmed
  3. Bataille D: [Molecular mechanisms of insulin secretion]. Diabetes Metab. 2002 Dec;28(6 Suppl):4S7-13. Pubmed

2. ATP-sensitive inward rectifier potassium channel 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
ATP-sensitive inward rectifier potassium channel 1 P48048 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Proks P, Reimann F, Green N, Gribble F, Ashcroft F: Sulfonylurea stimulation of insulin secretion. Diabetes. 2002 Dec;51 Suppl 3:S368-76. Pubmed
  4. Bataille D: [Molecular mechanisms of insulin secretion]. Diabetes Metab. 2002 Dec;28(6 Suppl):4S7-13. Pubmed

3. ATP-binding cassette sub-family C member 8

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inducer

Components

Name UniProt ID Details
ATP-binding cassette sub-family C member 8 Q09428 Details

References:

  1. Muller G, Hartz D, Punter J, Okonomopulos R, Kramer W: Differential interaction of glimepiride and glibenclamide with the beta-cell sulfonylurea receptor. I. Binding characteristics. Biochim Biophys Acta. 1994 May 11;1191(2):267-77. Pubmed
  2. Kramer W, Muller G, Geisen K: Characterization of the molecular mode of action of the sulfonylurea, glimepiride, at beta-cells. Horm Metab Res. 1996 Sep;28(9):464-8. Pubmed
  3. Kramer W, Muller G, Girbig F, Gutjahr U, Kowalewski S, Hartz D, Summ HD: The molecular interaction of sulfonylureas with beta-cell ATP-sensitive K(+)-channels. Diabetes Res Clin Pract. 1995 Aug;28 Suppl:S67-80. Pubmed

Enzymes

1. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 25, 2013 14:06