122647-32-9 Usage
Description
Ibutilide fumarate, also known as Inocor or Corvert, is a class III antiarrhythmic agent used for the treatment of atrial fibrillation and flutter. It is a methanesulfonanilide compound that prolongs myocardial action potential duration, predominantly by activation of slow inward sodium current. Ibutilide fumarate has an asymmetric center, but it has been determined that the racemate is equipotent with either enantiomer. The compound is a white to off-white solid and can be synthesized in three steps from N-phenyl methanesulfonamide.
Uses
Used in Pharmaceutical Industry:
Ibutilide fumarate is used as an antiarrhythmic agent for the treatment of atrial fibrillation and flutter. It works by prolonging the action potential duration and lengthening the refractory period of myocardial tissue. Class III antiarrhythmic agents, like ibutilide, achieve this effect by blocking outward potassium channels or activating slow inward sodium channels. Recent evidence also suggests that ibutilide is a potent blocker of the rapidly acting delayed rectifier potassium current (Ikr) and may block the ATP-inhibited potassium channel.
Ibutilide fumarate is used as a pharmaceutical compound for the treatment of atrial arrhythmias. It inhibits the rapidly activating delayed-rectifier potassium current (IKr) in AT-1 myocytes with an IC50 value of 20 nM. Additionally, it enhances the late inward sodium current (INa) and increases the action potential duration in isolated guinea pig ventricular cells. Ibutilide fumarate 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. Furthermore, it increases the effective refractory period (ERP) of the left and right atrium in anesthetized pigs and 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.
Originator
Pharmacia ＆ Upjohn (UK)
Therapeutic Function
Antiarrhythmic
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.
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.
Side effects
The major adverse effect associated with the use of ibutilide
is the risk of torsades de pointes due to QT prolongation.
Other reported adverse cardiovascular
events (all 2%) include hypotension and hypertension,
bradycardia and tachycardia, and varying degrees
of A-V block. The incidence of noncardiac adverse
events with the exception of nausea does not differ
from that of placebo.
Drug interactions
Ibutilide has significant drug interactions.
Precautions
Contraindications to the use of ibutilide include baseline
prolongation of the QT interval, use of other QTprolonging
drugs, history of torsades de pointes, hypersensitivity
to ibutilide, uncorrected hypokalemia or
hypomagnesemia, and pregnancy or breast-feeding.
Check Digit Verification of cas no
The CAS Registry Mumber 122647-32-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,2,6,4 and 7 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 122647-32:
(8*1)+(7*2)+(6*2)+(5*6)+(4*4)+(3*7)+(2*3)+(1*2)=109
109 % 10 = 9
So 122647-32-9 is a valid CAS Registry Number.
InChI:InChI=1/C20H36N2O3S.C4H4O4/c1-4-6-7-8-9-16-22(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/h12-15,20-21,23H,4-11,16-17H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
122647-32-9Relevant articles and documents
A novel synthesis of ibutilide fumarate
Wang, Tao,Tian, Rui,Xiao, Bin,Shen, Yi,Zhou, Hui,Li, Qingeng
, p. 423 - 426 (2011)
A novel protocol for the synthesis of Ibutilide Fumarate (raceme) was achieved from 2-pyrrolidinone with an overall yield of 15%. The core structure was constructed in one step based on Friedel-Crafts acylation with an acyl chloride containing an amino hydrochloride.
