N-[4-(2-{[2-(4-methanesulfonamidophenoxy)ethyl](methyl)amino}ethyl)phenyl]methanesulfonamide

• ChemBase ID: 89
• Molecular Formular: C19H27N3O5S2
• Molecular Mass: 441.56478
• Monoisotopic Mass: 441.13921298
• SMILES: S(=O)(=O)(Nc1ccc(CCN(CCOc2ccc(NS(=O)(=O)C)cc2)C)cc1)C
• Canonical SMILES: CN(CCc1ccc(cc1)NS(=O)(=O)C)CCOc1ccc(cc1)NS(=O)(=O)C
• InChI: InChI=1S/C19H27N3O5S2/c1-22(13-12-16-4-6-17(7-5-16)20-28(2,23)24)14-15-27-19-10-8-18(9-11-19)21-29(3,25)26/h4-11,20-21H,12-15H2,1-3H3
• InChIKey: IXTMWRCNAAVVAI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[4-(2-{[2-(4-methanesulfonamidophenoxy)ethyl](methyl)amino}ethyl)phenyl]methanesulfonamide
• IUPAC Traditional name: N-[4-(2-{[2-(4-methanesulfonamidophenoxy)ethyl](methyl)amino}ethyl)phenyl]methanesulfonamide
• Brand Name: Dofetilida; Tikosyn
• Synonyms: Dofetilida [INN-Spanish]; Dofetilidum [INN-Latin]; Dofetilide; Tikosyn; UK68798; N-[4-[2-[Methyl[2-[4-[(methylsulfonyl)amino]phenoxy]ethyl]amino]ethyl]phenyl]methanesulfonamide; UK-68798; Dofetilide

Database IDs

• CAS Number: 115256-11-6
• MDL Number: MFCD00869707
• PubChem SID: 46509127; 160963552
• PubChem CID: 71329

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.145184
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.6246078
• LogD (pH = 7.4): -1.0490478
• Log P: 0.23791575
• Molar Refractivity: 113.2743 cm^3
• Polarizability: 45.58207 Å^3
• Polar Surface Area: 104.81 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.17
• LOG S: -4.35
• Solubility (Water): 1.98e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white to off-white powder
• Hydrophobicity(logP): 2.1

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• German water hazard class: nwg
• Risk Statements: 61-48/22-51
• Safety Statements: 53-22-36-57
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H360
• GHS Precautionary statements: P201-P308 + P313
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C19H27N3O5S2

DETAILS

DrugBank - DB00204

• Drug Groups: approved
• Description: Dofetilide is a class III antiarrhythmic agent that is approved by the Food and Drug Administration (FDA) for the maintenance of sinus rhythm in individuals prone to the formation of atrial fibrillation and flutter, and for the chemical cardioversion to sinus rhythm from atrial fibrillation and flutter. [Wikipedia]
• Indication: For the maintenance of normal sinus rhythm (delay in time to recurrence of atrial fibrillation/atrial flutter [AF/AFl]) in patients with atrial fibrillation/atrial flutter of greater than one week duration who have been converted to normal sinus rhythm
• Pharmacology: Dofetilide is an antiarrhythmic drug with Class III (cardiac action potential duration prolonging) properties and is indicated for the maintenance of normal sinus rhythm. Dofetilide increases the monophasic action potential duration in a predictable, concentration-dependent manner, primarily due to delayed repolarization. At concentrations covering several orders of magnitude, Dofetilide blocks only IKr with no relevant block of the other repolarizing potassium currents (e.g., IKs, IK1). At clinically relevant concentrations, Dofetilide has no effect on sodium channels (associated with Class I effect), adrenergic alpha-receptors, or adrenergic beta-receptors.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: >90%
• Half Life: 10 hours
• Protein Binding: 60% -70%
• Distribution: * 3 L/kg
• References: Lenz TL, Hilleman DE: Dofetilide, a new class III antiarrhythmic agent. Pharmacotherapy. 2000 Jul;20(7):776-86. [Pubmed] ; Lenz TL, Hilleman DE: Dofetilide: A new antiarrhythmic agent approved for conversion and/or maintenance of atrial fibrillation/atrial flutter. Drugs Today (Barc). 2000 Nov;36(11):759-71. [Pubmed] ; Torp-Pedersen C, Moller M, Bloch-Thomsen PE, Kober L, Sandoe E, Egstrup K, Agner E, Carlsen J, Videbaek J, Marchant B, Camm AJ: Dofetilide in patients with congestive heart failure and left ventricular dysfunction. Danish Investigations of Arrhythmia and Mortality on Dofetilide Study Group. N Engl J Med. 1999 Sep 16;341(12):857-65. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1658

Research Area: Cardiovascular Disease
Biological Activity:
Dofetilide(Tikosyn) is a class III antiarrhythmic agent.The elimination half-life of dofetilide is roughly 10 hours, however this is variable based on many physiologic factors (most significantly creatinine clearance), and ranges from 4.8 to 13.5 hours. [1]

Sigma Aldrich - PZ0016

Biochem/physiol Actions
Dofetilide is a Class III antiarrhythmic and hERG channel blocker. Dofetilide selectively blocks the rapid component of the delayed rectifier outward potassium current (IKr).
Legal Information
Sold for research purposes under agreement from Pfizer Inc.

REFERENCES

• Lenz TL, Hilleman DE: Dofetilide, a new class III antiarrhythmic agent. Pharmacotherapy. 2000 Jul;20(7):776-86. Pubmed
• Lenz TL, Hilleman DE: Dofetilide: A new antiarrhythmic agent approved for conversion and/or maintenance of atrial fibrillation/atrial flutter. Drugs Today (Barc). 2000 Nov;36(11):759-71. Pubmed
• Torp-Pedersen C, Moller M, Bloch-Thomsen PE, Kober L, Sandoe E, Egstrup K, Agner E, Carlsen J, Videbaek J, Marchant B, Camm AJ: Dofetilide in patients with congestive heart failure and left ventricular dysfunction. Danish Investigations of Arrhythmia and Mortality on Dofetilide Study Group. N Engl J Med. 1999 Sep 16;341(12):857-65. Pubmed
• http://en.wikipedia.org/wiki/Dofetilide