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Details

Stereochemistry RACEMIC
Molecular Formula C20H36N2O3S
Molecular Weight 384.576
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IBUTILIDE

SMILES

CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1

InChI

InChIKey=ALOBUEHUHMBRLE-UHFFFAOYSA-N
InChI=1S/C20H36N2O3S/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/h12-15,20-21,23H,4-11,16-17H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C20H36N2O3S
Molecular Weight 384.576
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Ibutilide is a 'pure' class III antiarrhythmic drug, used intravenously against atrial flutter and fibrillation. At a cellular level it exerts two main actions: induction of a persistent Na+ current sensitive to dihydropyridine Ca2+ channel blockers and potent inhibition of the cardiac rapid delayed rectifier K+ current, by binding within potassium channel pores. In other words, Ibutilide binds to and alters the activity of hERG potassium channels, delayed inward rectifier potassium (IKr) channels and L-type (dihydropyridine sensitive) calcium channels. Ibutilide is indicated for the rapid conversion of atrial fibrillation or atrial flutter of recent onset to sinus rhythm. Ibutilide is marketed as Corvert by Pfizer.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.9 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CORVERT

Cmax

ValueDoseCo-administeredAnalytePopulation
5.8 μg/L
1 mg single, intravenous
IBUTILIDE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
177 μg × min/L
1 mg single, intravenous
IBUTILIDE plasma
Homo sapiens
13.2 μg × h/L
1 mg single, intravenous
IBUTILIDE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
9.1 h
1 mg single, intravenous
IBUTILIDE plasma
Homo sapiens
12.4 h
1 mg single, intravenous
IBUTILIDE serum
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Atrial Fibrillation 60 kg or more: 1 mg IV over 10 minutes; if arrhythmia persists 10 minutes after the end of the first infusion, repeat once. Less than 60 kg: 0.01 mg/kg IV over 10 minutes; if arrhythmia persists 10 minutes after the end of the first infusion, repeat once.
Route of Administration: Intravenous
In Vitro Use Guide
Ibutilide at the 10(-5) M effective refractory periods at 1 and 3 Hz increased by 18-32 ms, conduction times measured at 3 Hz increased by 27-30% and atrial rate decreased by 19-32% in isolated rabbit myocardium.
Substance Class Chemical
Record UNII
2436VX1U9B
Record Status Validated (UNII)
Record Version