Dofetilide (CHEM018989)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:44:17 UTC
Update Date2026-04-13 20:29:19 UTC
Accession NumberCHEM018989
Identification
Common NameDofetilide
ClassSmall Molecule
DescriptionDofetilide 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
beta-((p-Methanesulfonamidophenethyl)methylamino)methanesulfono-p-phenetidideChEBI
DofetilidaChEBI
DofetilidumChEBI
TikosynChEBI
b-((p-Methanesulfonamidophenethyl)methylamino)methanesulfono-p-phenetidideGenerator
b-((p-Methanesulphonamidophenethyl)methylamino)methanesulphono-p-phenetidideGenerator
beta-((p-Methanesulphonamidophenethyl)methylamino)methanesulphono-p-phenetidideGenerator
Β-((p-methanesulfonamidophenethyl)methylamino)methanesulfono-p-phenetidideGenerator
Β-((p-methanesulphonamidophenethyl)methylamino)methanesulphono-p-phenetidideGenerator
1-MSPMPEHMDB
1-(4-Methanesulfonamidophenoxy)-2-(N-(4-methanesulfonamidophenethyl)-N-methylamine)ethaneHMDB
Chemical FormulaC19H27N3O5S2
Average Molecular Mass441.565 g/mol
Monoisotopic Mass441.139 g/mol
CAS Registry Number115256-11-6
IUPAC NameN-[4-(2-{[2-(4-methanesulfonamidophenyl)ethyl](methyl)amino}ethoxy)phenyl]methanesulfonamide
Traditional Namedofetilide
SMILESCN(CCOC1=CC=C(NS(C)(=O)=O)C=C1)CCC1=CC=C(NS(C)(=O)=O)C=C1
InChI IdentifierInChI=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
InChI KeyIXTMWRCNAAVVAI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassSulfanilides
Direct ParentSulfanilides
Alternative Parents
Substituents
  • Sulfanilide
  • Phenethylamine
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Aralkylamine
  • Organic sulfonic acid amide
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP2.17ALOGPS
logP0.24ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)10.15ChemAxon
pKa (Strongest Basic)8.99ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.81 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity113.27 m³·mol⁻¹ChemAxon
Polarizability46.03 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvl-4932000000-66e362c3fe81fb58fcc7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-1610900000-368db21beef81a5319f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0300900000-47394a7ed027cb5ab3cfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0200900000-5e88add5ce502b3def00Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0007-0930700000-c49a09c3642ebe80a508Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0005-0029400000-8d71d52f4a3c4cc520cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0494000000-29318a7a4e340a84b89cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc1-0970000000-ff7ab38dee25c13c628eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-7210900000-61f7904544738c663c26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9211100000-40309ebd6f3c937574a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-efa6a192289b1224a063Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-562b19ba98459c2cd026Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9100700000-141e753d4ef538c9f060Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9400000000-def4b905438245c50110Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000900000-14da12b317cbb5fefb49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052g-0481900000-6143e73095a8c3c8a7c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0910000000-66e5293cc76f8e2d917aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00204
HMDB IDHMDB0014349
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDofetilide
Chemspider ID64435
ChEBI ID4681
PubChem Compound ID71329
Kegg Compound IDC07751
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. Lenz TL, Hilleman DE: Dofetilide, a new class III antiarrhythmic agent. Pharmacotherapy. 2000 Jul;20(7):776-86.
3. 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.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11326815
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25620152
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25626340