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Details

Stereochemistry RACEMIC
Molecular Formula C20H36N2O3S
Molecular Weight 384.5783
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IBUTILIDE

SMILES

CCCCCCCN(CC)CCCC(c1ccc(cc1)NS(=O)(=O)C)O

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 384.5783
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/cdi/ibutilide.html

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

Curator's Comment:: # Pfizer

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q02641
Gene ID: 782.0
Gene Symbol: CACNB1
Target Organism: Homo sapiens (Human)
Target ID: CHEMBL240
0.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CORVERT

Approved Use

indicated for the rapid conversion of atrial fibrillation or atrial flutter of recent onset to sinus rhythm.

Launch Date

8.2002241E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.8 μg/L
1 mg single, intravenous
dose: 1 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IBUTILIDE unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
177 μg × min/L
1 mg single, intravenous
dose: 1 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IBUTILIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
13.2 μg × h/L
1 mg single, intravenous
dose: 1 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IBUTILIDE unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.1 h
1 mg single, intravenous
dose: 1 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IBUTILIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
12.4 h
1 mg single, intravenous
dose: 1 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IBUTILIDE unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 mg single, intravenous
Highest studied dose
Dose: 1 mg
Route: intravenous
Route: single
Dose: 1 mg
Sources:
healthy, adult
n = 8
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 8
Sources:
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Disc. AE: Extrasystoles ventricular, Non-sustained ventricular tachycardia...
Other AEs: Chest pain, Bradycardia...
AEs leading to
discontinuation/dose reduction:
Extrasystoles ventricular (3.7%)
Non-sustained ventricular tachycardia (3.4%)
Non-sustained ventricular tachycardia (3.5%)
Polymorphic ventricular tachycardia (1.8%)
Other AEs:
Chest pain (2.6%)
Bradycardia (1.4%)
Hypotension (2.6%)
Sinus bradycardia (1.2%)
Heart arrest (1%)
Headache (4.1%)
Procedural complication (1.9%)
Nausea (4.8%)
Dizziness (1.8%)
Diarrhea (1.8%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Heart arrest 1%
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Sinus bradycardia 1.2%
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Bradycardia 1.4%
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Diarrhea 1.8%
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Dizziness 1.8%
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Polymorphic ventricular tachycardia 1.8%
Disc. AE
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Procedural complication 1.9%
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Chest pain 2.6%
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Hypotension 2.6%
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Non-sustained ventricular tachycardia 3.4%
Disc. AE
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Non-sustained ventricular tachycardia 3.5%
Disc. AE
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Extrasystoles ventricular 3.7%
Disc. AE
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Headache 4.1%
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Nausea 4.8%
1 mg 1 times / 10 min multiple, intravenous
Recommended
Dose: 1 mg, 1 times / 10 min
Route: intravenous
Route: multiple
Dose: 1 mg, 1 times / 10 min
Sources:
unhealthy, adult
n = 776
Health Status: unhealthy
Condition: atrial flutter or atrial fibrillation
Age Group: adult
Population Size: 776
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Acute renal failure after ibutilide.
1999 Feb 6
Usefulness of ibutilide in facilitating successful external cardioversion of refractory atrial fibrillation.
1999 Nov 1
Termination of recent-onset atrial fibrillation/flutter in the emergency department: a sequential approach with intravenous ibutilide and external electrical cardioversion.
2000 Aug 1
Drug-induced QT prolongation in women during the menstrual cycle.
2001 Mar 14
[Severe ibutilide-induced arrhythmia in patients with heart failure].
2001 Oct 10
Comparison of verapamil and ibutilide for the suppression of immediate recurrences of atrial fibrillation after transthoracic cardioversion.
2002 Jul
Conversion of recent-onset atrial fibrillation or flutter with ibutilide after amiodarone has failed.
2002 Jul
Prediction of hERG potassium channel affinity by traditional and hologram qSAR methods.
2003 Aug 18
The role of amiodarone in recent-onset atrial fibrillation after ibutilide has failed to restore sinus rhythm.
2007
Autonomic tone attenuates drug-induced QT prolongation.
2007 Sep
Relationship among amiodarone, new class III antiarrhythmics, miscellaneous agents and acquired long QT syndrome.
2008
Pharmacokinetics of ibutilide in patients with heart failure due to left ventricular systolic dysfunction.
2008 Dec
Pharmacology of the short QT syndrome N588K-hERG K+ channel mutation: differential impact on selected class I and class III antiarrhythmic drugs.
2008 Nov
Effects of ibutilide on inhibiting heart rate and rapidly terminating atrial flutter in canine.
2011 Apr
Patents

Patents

Sample Use Guides

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
Created
by admin
on Sat Jun 26 16:22:51 UTC 2021
Edited
by admin
on Sat Jun 26 16:22:51 UTC 2021
Record UNII
2436VX1U9B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IBUTILIDE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
IBUTILIDE [VANDF]
Common Name English
IBUTILIDE [INN]
Common Name English
IBUTILIDE [WHO-DD]
Common Name English
IBUTILIDE [MI]
Common Name English
METHANESULFONAMIDE, N-(4-(4-(ETHYLHEPTYLAMINO)-1-HYDROXYBUTYL)PHENYL)-
Systematic Name English
N-(4-(4-(ETHYL(HEPTYL)AMINO)-1-HYDROXYBUTYL)PHENYL)METHANESULFONAMIDE
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000175426
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
NCI_THESAURUS C47793
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
WHO-ATC C01BD05
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
NCI_THESAURUS C93038
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
WHO-VATC QC01BD05
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C72581
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
DRUG CENTRAL
1412
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
WIKIPEDIA
IBUTILIDE
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
MESH
C067192
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
DRUG BANK
DB00308
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
ChEMBL
CHEMBL533
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
RXCUI
41289
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY RxNorm
INN
6642
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
FDA UNII
2436VX1U9B
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
IUPHAR
7200
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
PUBCHEM
60753
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
MERCK INDEX
M6191
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY Merck Index
EVMPD
SUB08102MIG
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
HSDB
7926
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
CAS
122647-31-8
Created by admin on Sat Jun 26 16:22:52 UTC 2021 , Edited by admin on Sat Jun 26 16:22:52 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC