Ibutilide fumarate | CAS#122647-32-9 | antiarrhythmic agent

MedKoo Cat#: 318051 | Name: Ibutilide fumarate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ibutilide fumarate is a Class III antiarrhythmic agent that is indicated for acute cardioconversion of atrial fibrillation and atrial flutter of a recent onset to sinus rhythm. It exerts its antiarrhythmic effect by induction of slow inward sodium current, which prolongs action potential and refractory period (physiology) of myocardial cells.

Chemical Structure

Ibutilide fumarate

CAS#122647-32-9

Theoretical Analysis

MedKoo Cat#: 318051

Name: Ibutilide fumarate

CAS#: 122647-32-9

Chemical Formula: C20H36N2O3S

Exact Mass: 0.0000

Molecular Weight: 384.58

Elemental Analysis: C, 62.46; H, 9.44; N, 7.28; O, 12.48; S, 8.34

Price and Availability

Size	Price	Availability
25mg	USD 285.00	2 Weeks
50mg	USD 500.00	2 Weeks
100mg	USD 850.00	2 Weeks

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Synonym

Ibutilide fumarate, Corvert, Ibutilida, Ibutilidum

IUPAC/Chemical Name

Methanesulfonamide, N-(4-(4-(ethylheptylamino)-1-hydroxybutyl)phenyl)-, (+-)-, (E)-2-butenedioate (2:1) (salt)

InChi Key

ALOBUEHUHMBRLE-UHFFFAOYSA-N

InChi Code

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

SMILES Code

CS(=O)(NC1=CC=C(C(O)CCCN(CC)CCCCCCC)C=C1)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ibutilide (U70226E) fumarate, an action potential-prolonging antiarrhythmic, is a potent blocker of the rapidly activating delayed rectifier K+ current (IKr) in AT-1 cells.

In vitro activity:

Ibutilide blocked IKr in cells expressing HERG+MDR1*1 to the same extent as cells expressing HERG alone (IC50: 22.5±0.9 vs 27.4±2.5 nM; P>0.05). This nanomolar block indicates that CHO cells take up ibutilide. However, cells expressing MDR1*7 showed a marked resistance to ibutilide (IC50: 105.3±1.42 nM vs 27.4±2.5 nM; P<0.0001). These data (Figures 2 and 3) suggest that the alanine-to-serine change generates a protein with the ability to enhance efflux of ibutilide. Reference: Pharmacogenomics J. 2009 Jun;9(3):194-201. https://pubmed.ncbi.nlm.nih.gov/19204737/

In vivo activity:

Pre-treatment of RNC with the cardioconversion drug ibutilide decreased the percentage of TUNEL positive cells by half (Fig 1A and 1B). These findings confirm tunicamycin treatment induces apoptosis in RNC (rat neonatal cardiomyocytes) and pre-treatment with ibutilide attenuates the extent of apoptosis. Reference: PLoS One. 2017 Apr 11;12(4):e0173469. https://pubmed.ncbi.nlm.nih.gov/28399139/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	78.01
	DMSO	41.4	107.70
	Ethanol	5.0	13.00
	PBS (pH 7.2)	1.0	2.26
	Water	47.1	122.55

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 384.58 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. McBride BF, Yang T, Roden DM. Influence of the G2677T/C3435T haplotype of MDR1 on P-glycoprotein trafficking and ibutilide-induced block of HERG. Pharmacogenomics J. 2009 Jun;9(3):194-201. doi: 10.1038/tpj.2009.1. Epub 2009 Feb 10. PMID: 19204737; PMCID: PMC3775644. 2. Yang T, Snyders DJ, Roden DM. Ibutilide, a methanesulfonanilide antiarrhythmic, is a potent blocker of the rapidly activating delayed rectifier K+ current (IKr) in AT-1 cells. Concentration-, time-, voltage-, and use-dependent effects. Circulation. 1995 Mar 15;91(6):1799-806. doi: 10.1161/01.cir.91.6.1799. PMID: 7882490. 3. Wang Y, Xuan L, Cui X, Wang Y, Chen S, Wei C, Zhao M. Ibutilide treatment protects against ER stress induced apoptosis by regulating calumenin expression in tunicamycin treated cardiomyocytes. PLoS One. 2017 Apr 11;12(4):e0173469. doi: 10.1371/journal.pone.0173469. PMID: 28399139; PMCID: PMC5388464. 4. Wang Y, Wang YL, Huang X, Yang Y, Zhao YJ, Wei CX, Zhao M. Ibutilide protects against cardiomyocytes injury via inhibiting endoplasmic reticulum and mitochondrial stress pathways. Heart Vessels. 2017 Feb;32(2):208-215. doi: 10.1007/s00380-016-0891-1. Epub 2016 Sep 17. Erratum in: Heart Vessels. 2017 Feb;32(2):216. PMID: 27639990; PMCID: PMC5288448.

In vitro protocol:

In vivo protocol:

1. Wang Y, Xuan L, Cui X, Wang Y, Chen S, Wei C, Zhao M. Ibutilide treatment protects against ER stress induced apoptosis by regulating calumenin expression in tunicamycin treated cardiomyocytes. PLoS One. 2017 Apr 11;12(4):e0173469. doi: 10.1371/journal.pone.0173469. PMID: 28399139; PMCID: PMC5388464. 2. Wang Y, Wang YL, Huang X, Yang Y, Zhao YJ, Wei CX, Zhao M. Ibutilide protects against cardiomyocytes injury via inhibiting endoplasmic reticulum and mitochondrial stress pathways. Heart Vessels. 2017 Feb;32(2):208-215. doi: 10.1007/s00380-016-0891-1. Epub 2016 Sep 17. Erratum in: Heart Vessels. 2017 Feb;32(2):216. PMID: 27639990; PMCID: PMC5288448.

1: Nair M, George LK, Koshy SK. Safety and efficacy of ibutilide in cardioversion of atrial flutter and fibrillation. J Am Board Fam Med. 2011 Jan-Feb;24(1):86-92. doi: 10.3122/jabfm.2011.01.080096. Review. PubMed PMID: 21209348. 2: Doggrell SA, Hancox JC. Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. Review. PubMed PMID: 15926871. 3: Rogers KC, Wolfe DA. Ibutilide: a class III rapidly acting antidysrhythmic for atrial fibrillation or atrial flutter. J Emerg Med. 2001 Jan;20(1):67-71. Review. PubMed PMID: 11165840. 4: Kaufman LJ, Kofalvi AE, Hong RA, Moreno-Cabral CE, Low LL. Cardioversion of atrial fibrillation with ibutilide in an orthotopic heart transplant patient. J Heart Lung Transplant. 1999 Oct;18(10):1018-20. Review. PubMed PMID: 10561113. 5: Granberry MC. Ibutilide: a new class III antiarrhythmic agent. Am J Health Syst Pharm. 1998 Feb 1;55(3):255-60. Review. PubMed PMID: 9492255. 6: Murray KT. Ibutilide. Circulation. 1998 Feb 10;97(5):493-7. Review. PubMed PMID: 9490245. 7: Foster RH, Wilde MI, Markham A. Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. Review. PubMed PMID: 9257085. 8: Pill MW. Ibutilide: a new antiarrhythmic agent for the critical care environment. Crit Care Nurse. 1997 Jun;17(3):19-22. Review. PubMed PMID: 9313408. 9: Kowey PR, VanderLugt JT, Luderer JR. Safety and risk/benefit analysis of ibutilide for acute conversion of atrial fibrillation/flutter. Am J Cardiol. 1996 Oct 17;78(8A):46-52. Review. PubMed PMID: 8903276. 10: Naccarelli GV, Lee KS, Gibson JK, VanderLugt J. Electrophysiology and pharmacology of ibutilide. Am J Cardiol. 1996 Oct 17;78(8A):12-6. Review. PubMed PMID: 8903270. 11: Gowda RM, Khan IA, Punukollu G, Vasavada BC, Sacchi TJ, Wilbur SL. Female preponderance in ibutilide-induced torsade de pointes. Int J Cardiol. 2004 Jun;95(2-3):219-22. Review. PubMed PMID: 15193823. 12: Howard PA. Ibutilide: an antiarrhythmic agent for the treatment of atrial fibrillation or flutter. Ann Pharmacother. 1999 Jan;33(1):38-47. Review. PubMed PMID: 9972384. 13: Obel OA, Camm AJ. The use of drugs for cardioversion of recent onset atrial fibrillation and flutter. Focus on ibutilide. Drugs Aging. 1998 Jun;12(6):461-76. Review. PubMed PMID: 9638394. 14: Strimike CL, Wojcik JM. Stopping atrial fibrillation with ibutilide. Am J Nurs. 1998 Jan;98(1):32-4. Review. PubMed PMID: 9455330. 15: Cropp JS, Antal EG, Talbert RL. Ibutilide: a new class III antiarrhythmic agent. Pharmacotherapy. 1997 Jan-Feb;17(1):1-9. Review. PubMed PMID: 9017761. 16: Ellenbogen KA, Clemo HF, Stambler BS, Wood MA, VanderLugt JT. Efficacy of ibutilide for termination of atrial fibrillation and flutter. Am J Cardiol. 1996 Oct 17;78(8A):42-5. Review. PubMed PMID: 8903275. 1: Nair M, George LK, Koshy SK. Safety and efficacy of ibutilide in cardioversion of atrial flutter and fibrillation. J Am Board Fam Med. 2011 Jan-Feb;24(1):86-92. doi: 10.3122/jabfm.2011.01.080096. Review. PubMed PMID: 21209348. 2: Doggrell SA, Hancox JC. Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. Review. PubMed PMID: 15926871. 3: Rogers KC, Wolfe DA. Ibutilide: a class III rapidly acting antidysrhythmic for atrial fibrillation or atrial flutter. J Emerg Med. 2001 Jan;20(1):67-71. Review. PubMed PMID: 11165840. 4: Kaufman LJ, Kofalvi AE, Hong RA, Moreno-Cabral CE, Low LL. Cardioversion of atrial fibrillation with ibutilide in an orthotopic heart transplant patient. J Heart Lung Transplant. 1999 Oct;18(10):1018-20. Review. PubMed PMID: 10561113. 5: Granberry MC. Ibutilide: a new class III antiarrhythmic agent. Am J Health Syst Pharm. 1998 Feb 1;55(3):255-60. Review. PubMed PMID: 9492255. 6: Murray KT. Ibutilide. Circulation. 1998 Feb 10;97(5):493-7. Review. PubMed PMID: 9490245. 7: Foster RH, Wilde MI, Markham A. Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. Review. PubMed PMID: 9257085. 8: Pill MW. Ibutilide: a new antiarrhythmic agent for the critical care environment. Crit Care Nurse. 1997 Jun;17(3):19-22. Review. PubMed PMID: 9313408. 9: Kowey PR, VanderLugt JT, Luderer JR. Safety and risk/benefit analysis of ibutilide for acute conversion of atrial fibrillation/flutter. Am J Cardiol. 1996 Oct 17;78(8A):46-52. Review. PubMed PMID: 8903276. 10: Naccarelli GV, Lee KS, Gibson JK, VanderLugt J. Electrophysiology and pharmacology of ibutilide. Am J Cardiol. 1996 Oct 17;78(8A):12-6. Review. PubMed PMID: 8903270. 11: Gowda RM, Khan IA, Punukollu G, Vasavada BC, Sacchi TJ, Wilbur SL. Female preponderance in ibutilide-induced torsade de pointes. Int J Cardiol. 2004 Jun;95(2-3):219-22. Review. PubMed PMID: 15193823. 12: Howard PA. Ibutilide: an antiarrhythmic agent for the treatment of atrial fibrillation or flutter. Ann Pharmacother. 1999 Jan;33(1):38-47. Review. PubMed PMID: 9972384. 13: Obel OA, Camm AJ. The use of drugs for cardioversion of recent onset atrial fibrillation and flutter. Focus on ibutilide. Drugs Aging. 1998 Jun;12(6):461-76. Review. PubMed PMID: 9638394. 14: Strimike CL, Wojcik JM. Stopping atrial fibrillation with ibutilide. Am J Nurs. 1998 Jan;98(1):32-4. Review. PubMed PMID: 9455330. 15: Cropp JS, Antal EG, Talbert RL. Ibutilide: a new class III antiarrhythmic agent. Pharmacotherapy. 1997 Jan-Feb;17(1):1-9. Review. PubMed PMID: 9017761. 16: Ellenbogen KA, Clemo HF, Stambler BS, Wood MA, VanderLugt JT. Efficacy of ibutilide for termination of atrial fibrillation and flutter. Am J Cardiol. 1996 Oct 17;78(8A):42-5. Review. PubMed PMID: 8903275.