N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide

• ChemBase编号: 193
• 分子式: C20H36N2O3S
• 平均质量: 384.57644
• 单一同位素质量: 384.24466402
• SMILES: c1(ccc(cc1)NS(=O)(=O)C)C(CCCN(CC)CCCCCCC)O
• Canonical SMILES: CCCCCCCN(CCCC(c1ccc(cc1)NS(=O)(=O)C)O)CC
• InChI: InChI=1S/C20H36N2O3S/c1-4-6-7-8-9-16-22(5-2)17-10-11-20(23)18-12-14-19(15-13-18)21-26(3,24)25/h12-15,20-21,23H,4-11,16-17H2,1-3H3
• InChIKey: ALOBUEHUHMBRLE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide
• IUPAC传统名: @ibutilide; ibutilide
• 商标名: Corvert
• 别名: Ibutilide Fumarate; Ibutilida [INN-Spanish]; Ibutilide; Ibutilidum [INN-Latin]; Ibutilide; (+/-)-N-[4-[4-(Ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide Fumarate; Corvert; U 70226E; Ibutilide Fumarate

登记号

• CAS号: 122647-32-9
• PubChem SID: 160963656; 46507904
• PubChem CID: 60753

理论计算性质

JChem

• Acid pKa: 9.720055
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): -0.22546837
• LogD (pH = 7.4): 0.52760005
• Log P: 2.5426521
• 摩尔折射率: 109.1816 cm^3
• 极化性: 43.551353 Å^3
• 极化表面积: 69.64 Å^2
• 可自由旋转的化学键: 13
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.72
• LOG S: -4.91
• 溶解度: 4.73e-03 g/l

分子性质

理化性质

• 溶解度: 100 mg/mL; DMSO; Methanol; Water
• 外观: White to Off-White Solid
• 熔点: 112-117°C
• 疏水性(logP): 4.6

安全信息

• 保存条件: Refrigerator

详细说明

DrugBank - DB00308

• Drug Groups: approved
• Description: Ibutilide is a Class III antiarrhythmic agent that is indicated for acute cardioconversion of atrial fibrillation and atrial flutter of a recent onset to sinus rhythm. [Wikipedia]
• Indication: Indicated for the rapid conversion of atrial fibrillation or atrial flutter of recent onset to sinus rhythm.
• Pharmacology: Ibutilide prolongs the action potential duration and increases both atrial and ventricular refractoriness in vivo, i.e., class III electrophysiologic effects. Voltage clamp studies indicate that ibutilide, at nanomolar concentrations, delays repolarization by activation of a slow, inward current (predominantly sodium), rather than by blocking outward potassium currents, which is the mechanism by which most other class III antiarrhythmics act.
• Toxicity: Acute overdose in animals results in CNS toxicity; notably, CNS depression, rapid gasping breathing, and convulsions. The intravenous median lethal dose in the rat was more than 50 mg/kg which is, on a mg/m^2 basis, at least 250 times the maximum recommended human dose.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic. Eight metabolites of ibutilide were detected in metabolic profiling of urine. These metabolites are thought to be formed primarily by o-oxidation followed by sequential b-oxidation of the heptyl side chain of ibutilide. Of the eight metabolites, only the o-hydroxy metabolite possesses class III electrophysiologic properties similar to that of ibutilide in an in vitro isolated rabbit myocardium model.
• Absorption: Rapid after intravenous injection
• Half Life: 6 hours (ranges from 2-12 hours)
• Protein Binding: 40%
• Elimination: In healthy male volunteers, about 82% of a 0.01 mg/kg dose of [14C] ibutilide fumarate was excreted in the urine (about 7% of the dose as unchanged ibutilide) and the remainder (about 19%) was recovered in the feces.
• Distribution: * 11 L/kg
• Clearance: * 29 mL/min/kg
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - I155400

A methanesulfonanilide antiarrhythmic agent; prologns myocardial action potential duration, predominantly by activation of slow inward sodium current. Antiarrhythmic (class III).

参考文献

• Yang, T., et al.: Circulation, 91, 179 (1995)
• Stambler, B., et al.: Circulation, 94, 1613 (1995)
• Lee, K., et al.: J. Pharmacol. Exp. Ther., 286, 9 (1995)