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115256-11-6 molecular structure
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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 and InChIs

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

Cite this record

CBID:89 http://www.chembase.cn/molecule-89.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
N-[4-[2-[Methyl[2-[4-[(methylsulfonyl)amino]phenoxy]ethyl]amino]ethyl]phenyl]methanesulfonamide
Tikosyn
UK68798
UK-68798
Dofetilide
CAS Number
115256-11-6
MDL Number
MFCD00869707
PubChem SID
46509127
160963552
PubChem CID
71329

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.145184  H Acceptors
H Donor LogD (pH = 5.5) -2.6246078 
LogD (pH = 7.4) -1.0490478  Log P 0.23791575 
Molar Refractivity 113.2743 cm3 Polarizability 45.58207 Å3
Polar Surface Area 104.81 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.17  LOG S -4.35 
Solubility (Water) 1.98e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: >20 mg/mL expand Show data source
Apperance
white to off-white powder expand Show data source
Hydrophobicity(logP)
2.1 expand Show data source
Storage Condition
-20°C expand Show data source
European Hazard Symbols
Nature polluting Nature polluting (N) expand Show data source
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
nwg expand Show data source
Risk Statements
61-48/22-51 expand Show data source
Safety Statements
53-22-36-57 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H302-H360 expand Show data source
GHS Precautionary statements
P201-P308 + P313 expand Show data source
Storage Temperature
room temp expand Show data source
Purity
≥98% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Empirical Formula (Hill Notation)
C19H27N3O5S2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
DrugBank - DB00204 external link
Item Information
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 external link
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Dofetilide
  • • 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
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