bis(N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide); but-2-enedioic acid

• ChemBase ID: 154323
• Molecular Formular: C44H76N4O10S2
• Molecular Mass: 885.22504
• Monoisotopic Mass: 884.50028665
• SMILES: CCCCCCCN(CC)CCCC(c1ccc(cc1)NS(=O)(=O)C)O.CCCCCCCN(CC)CCCC(c1ccc(cc1)NS(=O)(=O)C)O.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: OC(=O)/C=C/C(=O)O.CCCCCCCN(CCCC(c1ccc(cc1)NS(=O)(=O)C)O)CC.CCCCCCCN(CCCC(c1ccc(cc1)NS(=O)(=O)C)O)CC
• InChI: InChI=1S/2C20H36N2O3S.C4H4O4/c2*1-4-6-7-8-9-16-22(5-2)17-10-11-20(23)18-12-14-19(15-13-18)21-26(3,24)25;5-3(6)1-2-4(7)8/h2*12-15,20-21,23H,4-11,16-17H2,1-3H3;1-2H,(H,5,6)(H,7,8)
• InChIKey: PCIOHQNIRPWFMV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide); but-2-enedioic acid; (2E)-but-2-enedioic acid; bis(N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide)
• IUPAC Traditional name: butenedioic acid; bis(ibutilide); fumaric acid; bis(ibutilide)
• Synonyms: bis(N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide); but-2-enedioic acid; (±)-N-[4-[4-(Ethylheptylamino)-1-hydroxybutyl]phenyl]-methanesulfonamide hemifumarate salt; Corvert; Ibutilide hemifumarate salt; Ibutilide fumarate

Database IDs

• CAS Number: 122647-32-9
• MDL Number: MFCD01715410
• PubChem SID: 162248462
• PubChem CID: 5281065

CALCULATED PROPERTIES

• 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: 28
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >20 mg/mL
• Apperance: off-white to tan solid
• Hydrophobicity(logP): 3.778

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: room temp

Pharmacology Properties

• Target: Sodium Channel

Product Information

• Purity: ≥98% (HPLC); 95%
• Salt Data: Fumarate
• Empirical Formula (Hill Notation): C20H36N2O3S · 0.5C4H4O4

DETAILS

Sigma Aldrich - I9910

Biochem/physiol Actions
Ibutilide hemifumarate salt is considered a new generation "pure" Class III antiarrhythmic agent. Ibutilide binds to and alters the activity of hERG potassium channels, delayed inward rectifier potassium (IKr) channels and L-type (dihydropyridine sensitive) calcium channels.