IBUTILIDE FUMARATE

Details

Stereochemistry	RACEMIC
Molecular Formula	2C20H36N2O3S.C4H4O4
Molecular Weight	885.225
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1.CCCCCCCN(CC)CCCC(O)C2=CC=C(NS(C)(=O)=O)C=C2

InChI

InChIKey=PCIOHQNIRPWFMV-WXXKFALUSA-N

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)/b;;2-1+

HIDE SMILES / InChI

Molecular Formula	C20H36N2O3S
Molecular Weight	384.576
Charge	0
Count

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

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00308
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Voltage-gated L-type calcium channel alpha-1C subunit 44 Target ID: CHEMBL1940 Sources: http://www.drugbank.ca/drugs/DB00308	Activator 1447
Voltage-dependent L-type calcium channel subunit beta-1 2 Target ID: Q02641 Gene ID: 782.0 Gene Symbol: CACNB1 Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00308	Activator 1447
HERG 99 Target ID: CHEMBL240 Sources: http://www.drugbank.ca/drugs/DB00308	Inhibitor 8504	0.9 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atrial fibrillation 131 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20-491S003.pdf	Primary		Approved 8583	CORVERT Approved Use indicated for the rapid conversion of atrial fibrillation or atrial flutter of recent onset to sinus rhythm. Launch Date 1995

C_max

Value	Dose	Co-administered	Analyte	Population
5.8 μg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19025427	1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered:		IBUTILIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
177 μg × min/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18035195	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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19025427	1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered:		IBUTILIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
9.1 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18035195	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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19025427	1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered:		IBUTILIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
1 mg single, intravenous Highest studied dose Dose: 1 mg Route: intravenous Route: single Dose: 1 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18035195/	healthy, adult Health Status: healthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/18035195/	Sources: https://pubmed.ncbi.nlm.nih.gov/18035195/
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf

AEs

AE	Significance	Dose	Population
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf
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: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.pfizer.ca/sites/default/files/201904/Corvert_PM_222103_29Mar2019_E.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946		substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12688833/ Page: 2.0	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12688833/ Page: 2.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.karger.com/Article/Pdf/111932

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY512832	https://www.001chemical.com/chem/122647-31-8
3B Scientific (Wuhan) Corp	3B2-1373	http://www.3bsc.com/index/pro_info.php?id=55089
AHH Chemical co.,ltd	MT-52774	http://www.ahhchemical.com/product/MT-52774.html
AK Scientific, Inc. (AKSCI)	71782	http://www.aksci.com/item_detail.php?cat=71782
AvaChem Scientific	2455B	http://www.avachem.com/productSearch.asp?2455B
BLD Pharm	BD134288	http://www.bldpharm.com/products/122647-31-8.html
BOC Sciences	122647-31-8	https://www.bocsci.com/ibutilide-cas-122647-31-8-item-56187.html
ChemMol	49421154	http://www.chemmol.com/chemmol/49421154.html
eNovation Chemicals	D674346	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674346
Finetech	FT-0631106	http://www.finetechnology-ind.com/prod/detail/pub/122647-31-8.html
Hairui	HR123088	http://www.hairuichem.com/en/product/122647-31-8.html
mcule	MCULE-5393489002	https://mcule.com/MCULE-5393489002/
Molcore	MC512832	https://www.molcore.com/product/122647-31-8
OChem	23480	http://www.ocheminc.com/index.php?act=psearch&pid=647I318
Sinfoo Biotech	S007749	http://www.sinfoobiotech.com/product/1011147
Smolecule	S530325	http://www.smolecule.com/products/s530325
Smolecule	S580811	https://www.smolecule.com/products/s580811
THE BioTek	bt-269897	https://www.thebiotek.com/product/inhibitors/bt-269897
THE BioTek	bt-302102	https://www.thebiotek.com/product/others/bt-302102

PubMed

Title	Date	PubMed
Effects of ibutilide on inhibiting heart rate and rapidly terminating atrial flutter in canine.	2011-04	20972643
Pharmacokinetics of ibutilide in patients with heart failure due to left ventricular systolic dysfunction.	2008-12	19025427
Pharmacology of the short QT syndrome N588K-hERG K+ channel mutation: differential impact on selected class I and class III antiarrhythmic drugs.	2008-11	18724381
Relationship among amiodarone, new class III antiarrhythmics, miscellaneous agents and acquired long QT syndrome.	2008	18651412
Autonomic tone attenuates drug-induced QT prolongation.	2007-09	17666066
The role of amiodarone in recent-onset atrial fibrillation after ibutilide has failed to restore sinus rhythm.	2007	17284902
Use of ibutilide in cardioversion of patients with atrial fibrillation or atrial flutter treated with class IC agents.	2004-08-18	15312873
Structural determinants of HERG channel block by clofilium and ibutilide.	2004-08	15266014
Prediction of hERG potassium channel affinity by traditional and hologram qSAR methods.	2003-08-18	12873512
Ibutilide-induced long QT syndrome and torsade de pointes.	2002-11-09	12424513
Comparison of verapamil and ibutilide for the suppression of immediate recurrences of atrial fibrillation after transthoracic cardioversion.	2002-07	12232564
Conversion of recent-onset atrial fibrillation or flutter with ibutilide after amiodarone has failed.	2002-07	12122531
[Severe ibutilide-induced arrhythmia in patients with heart failure].	2001-10-10	11706492
Drug-induced QT prolongation in women during the menstrual cycle.	2001-03-14	11255387
Termination of recent-onset atrial fibrillation/flutter in the emergency department: a sequential approach with intravenous ibutilide and external electrical cardioversion.	2000-08-01	10959017
Usefulness of ibutilide in facilitating successful external cardioversion of refractory atrial fibrillation.	1999-11-01	10569674
Acute renal failure after ibutilide.	1999-02-06	9989724

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 Created by `admin` on `Mon Mar 31 18:25:48 GMT 2025` Edited by `admin` on `Mon Mar 31 18:25:48 GMT 2025`
Record UNII	9L5X4M5L6I
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

IBUTILIDE FUMARATE

Official Name

English

CORVERT

Preferred Name

English

METHANESULFONAMIDE, N-(4-(4-(ETHYLHEPTYLAMINO)-1-HYDROXYBUTYL)PHENYL)-, (±)-, (E)-2-BUTENEDIOATE (2:1) (SALT)

Common Name

English

IBUTILIDE FUMARATE [MI]

Common Name

English

(±)-4'-(4-(ETHYLHEPTYLAMINO)-1-HYDROXYBUTYL)METHANESULFONANILIDE FUMARATE (2:1) (SALT)

Common Name

English

IBUTILIDE FUMARATE [ORANGE BOOK]

Common Name

English

IBUTILIDE FUMARATE [USP MONOGRAPH]

Common Name

English

IBUTILIDE FUMARATE [USAN]

Common Name

English

Ibutilide fumarate [WHO-DD]

Common Name

English

N-(4-(4-(ETHYLHEPTYLAMINO)-1-HYDROXYBUTYL)PHENYL)METHANESULFONAMIDE (E)-2-BUTENEDIOATE (2:1 SALT)

Common Name

English

IBUTILIDE FUMARATE [USP-RS]

Common Name

English

IBUTILIDE FUMARATE [VANDF]

Common Name

English

U-70226E

Code

English

IBUTILIDE FUMARATE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47793