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

• ChemBase ID: 193
• Molecular Formular: C20H36N2O3S
• Molecular Mass: 384.57644
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide
• IUPAC Traditional name: @ibutilide; ibutilide
• Brand Name: Corvert
• Synonyms: Ibutilide Fumarate; Ibutilida [INN-Spanish]; Ibutilide; Ibutilidum [INN-Latin]; Ibutilide; (+/-)-N-[4-[4-(Ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide Fumarate; Corvert; U 70226E; Ibutilide Fumarate

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.720055
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.22546837
• LogD (pH = 7.4): 0.52760005
• Log P: 2.5426521
• Molar Refractivity: 109.1816 cm^3
• Polarizability: 43.551353 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.72
• LOG S: -4.91
• Solubility (Water): 4.73e-03 g/l

PROPERTIES

Physical Property

• Solubility: 100 mg/mL; DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 112-117°C
• Hydrophobicity(logP): 4.6

Safety Information

• Storage Condition: Refrigerator

DETAILS

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).

REFERENCES

• 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)