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

• ChemBase ID: 107
• Molecular Formular: C24H34N4O5S
• Molecular Mass: 490.61556
• Monoisotopic Mass: 490.22499121
• SMILES: S(=O)(=O)(NC(=O)NC1CCC(CC1)C)c1ccc(CCNC(=O)N2CC(=C(C2=O)CC)C)cc1
• Canonical SMILES: CCC1=C(C)CN(C1=O)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)NC1CCC(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)
• InChIKey: WIGIZIANZCJQQY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: amaryl
• Brand Name: Amarel; Amaryl; Endial; Novo-glimepiride; PMS-glimepiride; Ratio-glimepiride; Sandoz glimepiride
• Synonyms: Glimepirid; Glimepirida; Glimepiridum; Glimepride; Glimepiride

Database IDs

• CAS Number: 93479-97-1
• PubChem SID: 160963570; 46508842
• PubChem CID: 3476

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 2.82
• LOG S: -4.11
• Solubility (Water): 3.84e-02 g/l

PROPERTIES

Physical Property

• Solubility: Insoluble
• Hydrophobicity(logP): 3.5

DETAILS

DrugBank - DB00222

• Drug Groups: approved
• Description: Glimepiride is the first III generation sulphonyl urea it is a very potent sulphonyl urea with long duration of action.
• Indication: For concomitant use with insulin for the treatment of noninsulin-dependent (type 2) diabetes mellitus.
• Pharmacology: Glimepiride, 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.
• Toxicity: Severe hypoglycemic reactions with coma, seizure, or other neurological impairment.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Absorption: Completely (100%) absorbed following oral administration.
• Half Life: Approximately 5 hours following single dose.
• Protein Binding: Over 99.5% bound to plasma protein.
• 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]
• 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]
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