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

• ChemBase编号: 107
• 分子式: C24H34N4O5S
• 平均质量: 490.61556
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 3-ethyl-4-methyl-N-{2-[4-({[(4-methylcyclohexyl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide
• IUPAC传统名: amaryl
• 商标名: Amarel; Amaryl; Endial; Novo-glimepiride; PMS-glimepiride; Ratio-glimepiride; Sandoz glimepiride
• 别名: Glimepirid; Glimepirida; Glimepiridum; Glimepride; Glimepiride

登记号

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

理论计算性质

JChem

• Acid pKa: 4.3201776
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 2.3483384
• LogD (pH = 7.4): 2.180386
• Log P: 3.1205344
• 摩尔折射率: 129.8042 cm^3
• 极化性: 50.725914 Å^3
• 极化表面积: 124.68 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.82
• LOG S: -4.11
• 溶解度: 3.84e-02 g/l

分子性质

理化性质

• 溶解度: Insoluble
• 疏水性(logP): 3.5

详细说明

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]
• External Links: Wikipedia; RxList; Drugs.com