3-ethyl-4-methyl-2-oxo-N-(2-{4-[({[(1r,4r)-4-methylcyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)-2,5-dihydro-1H-pyrrole-1-carboxamide

• ChemBase ID: 72629
• Molecular Formular: C24H34N4O5S
• Molecular Mass: 490.61556
• Monoisotopic Mass: 490.22499121
• SMILES: c1c(ccc(c1)S(=O)(=O)NC(=O)N[C@@H]1CC[C@H](CC1)C)CCNC(=O)N1CC(=C(C1=O)CC)C
• Canonical SMILES: CCC1=C(C)CN(C1=O)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)N[C@@H]1CC[C@H](CC1)C
• 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-
• InChIKey: WIGIZIANZCJQQY-RUCARUNLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethyl-4-methyl-2-oxo-N-(2-{4-[({[(1r,4r)-4-methylcyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)-2,5-dihydro-1H-pyrrole-1-carboxamide
• IUPAC Traditional name: glimepride; glimepiride; 3-ethyl-4-methyl-2-oxo-N-(2-{4-[({[(1r,4r)-4-methylcyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)-2,5-dihydro-1H-pyrrole-1-carboxamide
• Synonyms: Glimepiride; trans-3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[trans-4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxyamide; Glimperide; HOE 490; Amaryl; Glista OD; Glimepiride; Glimepirid; Glimepirida; Glimepiridum; Glimepride; Amarel; Endial

Database IDs

• CAS Number: 93479-97-1; 93479-97-1
• MDL Number: MFCD00878417
• PubChem SID: 24895093; 162037554
• PubChem CID: 3476

CALCULATED PROPERTIES

• Acid pKa: 4.3201776
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.3483384
• LogD (pH = 7.4): 2.180386
• Log P: 3.1205344
• Molar Refractivity: 129.8042 cm^3
• Polarizability: 50.725914 Å^3
• Polar Surface Area: 124.68 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform (hot); DMSO: >10 mg/mL; Methanol (hot)
• Apperance: white solid; White Solid
• Melting Point: 199-201°C; 212.2-214.5 °C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: room temp

Pharmacology Properties

• Target: DPP-4
• Gene Information: human ... KCNJ1(3758)
• Mechanism of Action: Cyclooxygenase pathway inhibitor,; Potassium channel blocker

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Application(s): Hypoglycaemic agent
• Empirical Formula (Hill Notation): C24H34N4O5S

DETAILS

Selleck Chemicals - S1344

Research Area: Metabolic Disease
Biological Activity:
Glimepiride (Amaryl, Glista OD) is a medium-to-long acting sulfonylurea anti-diabetic compound with an ED50 of 182 μg/kg. [1] Glimepiride (Amaryl, Glista OD) is an oral blood-glucose-lowering agent of the sulfonylurea class. Like all sulfonylureas, glimepiride acts as a secretagogue. Glimepiride (Amaryl, Glista OD) lowers blood sugar by stimulating the release of insulin by pancreatic beta cells and by inducing increased activity of intracellular insulin receptors. [2]

Sigma Aldrich - G2295

Application
Glimepiride is currently used to treat type 2 diabetes.
Biochem/physiol Actions
Glimepiride is a potent blocker of cardiac KATP channels activated by pinacidil with an IC50 of 6.8 nM.

Toronto Research Chemicals - G410150

A sulfonylurea hypoglycemic agent. Used as an antidiabetic.

REFERENCES

• Ratheiser, K., et al.: Arzneim.-Forsch., 43, 856, (1993)
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• Donaubauer, H.H. et al., Arzneim.-Forsch., 1993, 43, 547; 1068, (tox, exp)
• Ratheiser, K. et al., Arzneim.-Forsch., 1993, 43, 856, (pharmacol, human)
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• Langtry, H.D. et al., Drugs, 1998, 55, 563-584, (rev)
• Nguyen, C. et al., Drugs of Today (Barcelona), 1998, 34, 391-400; 401-408, (rev)