Ibutilide Fumarate

Base Information

• Chemical Name: Ibutilide Fumarate
• CAS No.: 122647-32-9
• Deprecated CAS: 130350-52-6
• Molecular Formula: C44H76N4O10S2
• Molecular Weight: 885.36
• Hs Code.: 2935904000
• European Community (EC) Number: 687-381-2
• UNII: 9L5X4M5L6I
• ChEMBL ID: CHEMBL2355456
• DSSTox Substance ID: DTXSID8048652
• NCI Thesaurus Code: C47561
• RXCUI: 51256
• Wikidata: Q27272695
• Mol file: 122647-32-9.mol

Synonyms:Corvert;ibutilide;ibutilide fumarate;ibutilide, (+)-isomer;ibutilide, (+-)-isomer;ibutilide, (-)-isomer;ibutilide, fumarate salt (2:1), (+)-isomer;ibutilide, fumarate salt (2:1), (+-)-isomer;N-(4-(4-(ethylheptylamino)-1-hydroxybutyl)phenyl)methanesulfonamide;U-70226E;U-82208E;U-82209E;U82208E;U82209E

Chemical Property of Ibutilide Fumarate

Chemical Property:

• Vapor Pressure: 9.71E-12mmHg at 25°C
• Melting Point: 112-117?C
• Boiling Point: 522.4 °C at 760 mmHg
• Flash Point: 269.7 °C
• PSA: 230.64000
• LogP: 10.34740
• Storage Temp.: Refrigerator
• Solubility.: H2O: >20mg/mL
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 30
• Exact Mass: 884.50028698
• Heavy Atom Count: 60
• Complexity: 561

Purity/Quality:

99% ^*data from raw suppliers

Ibutilide fumarate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCN(CC)CCCC(C1=CC=C(C=C1)NS(=O)(=O)C)O.CCCCCCCN(CC)CCCC(C1=CC=C(C=C1)NS(=O)(=O)C)O.C(=CC(=O)O)C(=O)O
• Isomeric SMILES: CCCCCCCN(CC)CCCC(C1=CC=C(C=C1)NS(=O)(=O)C)O.CCCCCCCN(CC)CCCC(C1=CC=C(C=C1)NS(=O)(=O)C)O.C(=C/C(=O)O)\C(=O)O
• Recent ClinicalTrials: Vernakalant Versus Ibutilide In Recent-Onset Atrial Fibrillation
• Recent EU Clinical Trials: Vernakalant Versus Ibutilide In Recent-Onset Atrial Fibrillation
• Description: Covert was launched in the US and UK for treatment of atrial fibrillation and flutter and can be synthesized in three steps from N-phenyl rnethanesulfonamide. While ibutilide has an asymmetric center, it has been determined that the racemate is equipotent with either enantiomer. The antiarrhythmic action is derived from the compounds ability to prolong the action potential duration and lengthen the refractory period of myocardial tissue. Class Ⅲ antiarrhythrnic agents accomplish this by blocking outward potassium channels, however, ibutilide elicits the same effect by activation of slow inward sodium channels. Recent evidence indicates that it also is a potent blocker of the rapidly acting delayed rectifier potassium current (lkr)and may block the ATP-inhibited potassium channel. (±)-Ibutilide is a class III antiarrhythmic agent. It inhibits the rapidly activating delayed-rectifier potassium current (IKr) in AT-1 myocytes with an IC50 value of 20 nM. (±)-Ibutilide also enhances the late inward sodium current (INa) and increases the action potential duration in isolated guinea pig ventricular cells. It decreases ventricular fibrillation induced by the ATP-dependent potassium channel activator pinacidil in Langendorff isolated perfused rabbit hearts when used at concentrations ranging from 3 to 30 μM. (±)-Ibutilide (15 μg/kg, i.v.) increases the effective refractory period (ERP) of the left and right atrium in anesthetized pigs. It prevents rapid pacing-induced atrial flutter in dogs when administered orally at doses ranging from 0.25 to 5 mg/kg. Formulations containing ibutilide have been used in the treatment of atrial arrhythmias.
• Uses: A methanesulfonanilide antiarrhythmic agent; prologns myocardial action potential duration, predominantly by activation of slow inward sodium current. Antiarrhythmic (class III).
• Therapeutic Function: Antiarrhythmic
• Clinical Use: Ibutilide (Corvert) is a structural analog of sotalol and produces cardiac electrophysiological effects similar to those of the antiarrhythmic agents in class III. Ibutilide is approved for the chemical cardioversion of recent-onset atrial fibrillation and atrial flutter. Ibutilide appears to be more effective in terminating atrial flutter than atrial fibrillation. It can also lower the defibrillation threshold for atrial fibrillation resistant to chemical cardioversion.
• Drug interactions: Ibutilide has significant drug interactions.

Technology Process of Ibutilide Fumarate

There total 2 articles about Ibutilide Fumarate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

ibutilide (100632-81-3) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2) → ibutilide hemifumarate (122647-32-9)

Guidance literature:

In ethanol; at 20 ℃; for 2h;

DOI:10.2174/157017811796064412

Reference yield:

4-(ethylamino)butanoic acid hydrochloride (208402-95-3) → ibutilide hemifumarate (122647-32-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydroxide / water / 4 h / Cooling with ice; Reflux

2: thionyl chloride / dichloromethane / 2 h / Cooling with ice; Reflux

3: aluminum (III) chloride / carbon disulfide / 5 h / 0 °C

4: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 0 - 5 °C

5: ethanol / 2 h / 20 °C

With aluminum (III) chloride; lithium aluminium tetrahydride; thionyl chloride; sodium hydroxide; In tetrahydrofuran; carbon disulfide; ethanol; dichloromethane; water; 3: Friedel Crafts acylation;

DOI:10.2174/157017811796064412

upstream raw materials:

4-(ethylamino)butanoic acid hydrochloride

ibutilide

(2E)-but-2-enedioic acid

Refernces