KB-130015 | CAS#147030-48-6 | hERG1 potassium channel activator

MedKoo Cat#: 531993 | Name: KB-130015

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Description:

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

KB-130015 is an antiarrhythmic agent and a derivative of amiodarone. It inhibits potassium currents induced by acetylcholine or adenosine in isolated guinea pig atrial myocytes (IC50s = 0.82 and 0.57 µM, respectively). KB-130015 activates or inhibits the voltage-gated potassium channel human-ether-a-go-go (hERG), also known as Kv11.1, in HEK293 cells in a voltage-dependent manner. It activates large-conductance calcium-activated potassium (BKCa) channels in HEK293 cells expressing the BKCa subunit Slo1 (EC50 = 20.2 μM). KB-130015 (40 mg/kg) prolongs the duration of electrically stimulated action potentials in guinea pig papillary muscle ex vivo.1 It is also an antagonist of human thyroid hormone receptor α (TRα) and TRβ (IC50s = 2.2 and 4.1 µM, respectively, in reporter assays).

Chemical Structure

KB-130015

CAS#147030-48-6

Theoretical Analysis

MedKoo Cat#: 531993

Name: KB-130015

CAS#: 147030-48-6

Chemical Formula: C18H14I2O4

Exact Mass: 547.8981

Molecular Weight: 548.11

Elemental Analysis: C, 39.44; H, 2.57; I, 46.31; O, 11.68

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 385.00	2 Weeks
10mg	USD 700.00	2 Weeks

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Synonym

KB-130015; KB 130015; KB130015;

IUPAC/Chemical Name

2-[2,6-diiodo-4-[(2-methyl-1-benzofuran-3-yl)methyl]phenoxy]acetic acid

InChi Key

OLIKCJUMYWSDIV-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H14I2O4/c1-10-13(12-4-2-3-5-16(12)24-10)6-11-7-14(19)18(15(20)8-11)23-9-17(21)22/h2-5,7-8H,6,9H2,1H3,(H,21,22)

SMILES Code

O=C(O)COC1=C(I)C=C(CC2=C(C)OC3=C2C=CC=C3)C=C1I

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

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

KB130015 (KB015) is an orally active and potent ThRα and ThRβ (Thyroid Hormone Receptor) inhibitor, with IC50 values of 4.5 and 5.1 μM, respectively.

In vitro activity:

KB130015 and ibutilide in a concentration of 50 microM effectively inhibited the muscarinic potassium current. The effect was concentrationdependent and reversible. The half-maximum effective concentration was 0.8 microM (KB130015) and 2.8 microM (ibutilide). Reference: Med Klin (Munich). 2005 Nov 15;100(11):697-703. https://pubmed.ncbi.nlm.nih.gov/16328176/

In vivo activity:

Using segments of porcine pulmonary arteries, KB130015 induced endothelium-independent vasorelaxation, half-maximal at 43 microM KB130015. Relaxation was inhibited by 1 mM tetraethylammonium, suggesting that KB130015 can activate vascular smooth muscle type BK(Ca) channels under physiological conditions. Reference: Eur J Pharmacol. 2007 Jan 26;555(2-3):185-93. https://pubmed.ncbi.nlm.nih.gov/17134694/

	Solvent	mg/mL	mM
Solubility
	DMSO	10.0	18.24
	Ethanol	10.0	18.24

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 548.11 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. Gessner G, Macianskiene R, Starkus JG, Schönherr R, Heinemann SH. The amiodarone derivative KB130015 activates hERG1 potassium channels via a novel mechanism. Eur J Pharmacol. 2010 Apr 25;632(1-3):52-9. doi: 10.1016/j.ejphar.2010.01.010. Epub 2010 Jan 25. PMID: 20097192; PMCID: PMC2835770. 2. Borchard R, van Bracht M, Wickenbrock I, Prull MW, Pott L, Trappe HJ. Inhibition des muskarinergen Kaliumionenstroms durch das neue Klasse-III-Antiarrhythmikum KB130015 im Vergleich zu Ibutilide [Inhibition of the muscarinic potassium current by KB130015, a new antiarrhythmic agent to treat atrial fibrillation]. Med Klin (Munich). 2005 Nov 15;100(11):697-703. German. doi: 10.1007/s00063-005-1096-z. PMID: 16328176. 3. Gessner G, Heller R, Hoshi T, Heinemann SH. The amiodarone derivative 2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran (KB130015) opens large-conductance Ca2+-activated K+ channels and relaxes vascular smooth muscle. Eur J Pharmacol. 2007 Jan 26;555(2-3):185-93. doi: 10.1016/j.ejphar.2006.10.053. Epub 2006 Oct 28. PMID: 17134694. 4. Bito V, Dauwe D, Verdonck F, Mubagwa K, Sipido KR. The amiodarone derivative KB130015 [2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran] induces an Na+-dependent increase of [Ca2+] in ventricular myocytes. J Pharmacol Exp Ther. 2006 Jan;316(1):162-8. doi: 10.1124/jpet.105.092221. Epub 2005 Sep 16. PMID: 16169937.

In vitro protocol:

In vivo protocol:

. Gessner G, Heller R, Hoshi T, Heinemann SH. The amiodarone derivative 2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran (KB130015) opens large-conductance Ca2+-activated K+ channels and relaxes vascular smooth muscle. Eur J Pharmacol. 2007 Jan 26;555(2-3):185-93. doi: 10.1016/j.ejphar.2006.10.053. Epub 2006 Oct 28. PMID: 17134694. 2. Bito V, Dauwe D, Verdonck F, Mubagwa K, Sipido KR. The amiodarone derivative KB130015 [2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran] induces an Na+-dependent increase of [Ca2+] in ventricular myocytes. J Pharmacol Exp Ther. 2006 Jan;316(1):162-8. doi: 10.1124/jpet.105.092221. Epub 2005 Sep 16. PMID: 16169937.

1: Gessner G, Macianskiene R, Starkus JG, Schönherr R, Heinemann SH. The amiodarone derivative KB130015 activates hERG1 potassium channels via a novel mechanism. Eur J Pharmacol. 2010 Apr 25;632(1-3):52-9. doi: 10.1016/j.ejphar.2010.01.010. Epub 2010 Jan 25. PMID: 20097192; PMCID: PMC2835770. 2: Gessner G, Heller R, Hoshi T, Heinemann SH. The amiodarone derivative 2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran (KB130015) opens large- conductance Ca2+-activated K+ channels and relaxes vascular smooth muscle. Eur J Pharmacol. 2007 Jan 26;555(2-3):185-93. doi: 10.1016/j.ejphar.2006.10.053. Epub 2006 Oct 28. PMID: 17134694. 3: Borchard R, van Bracht M, Wickenbrock I, Prull MW, Pott L, Trappe HJ. Inhibition des muskarinergen Kaliumionenstroms durch das neue Klasse-III- Antiarrhythmikum KB130015 im Vergleich zu Ibutilide [Inhibition of the muscarinic potassium current by KB130015, a new antiarrhythmic agent to treat atrial fibrillation]. Med Klin (Munich). 2005 Nov 15;100(11):697-703. German. doi: 10.1007/s00063-005-1096-z. PMID: 16328176. 4: Bito V, Dauwe D, Verdonck F, Mubagwa K, Sipido KR. The amiodarone derivative KB130015 [2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran] induces an Na+-dependent increase of [Ca2+] in ventricular myocytes. J Pharmacol Exp Ther. 2006 Jan;316(1):162-8. doi: 10.1124/jpet.105.092221. Epub 2005 Sep 16. PMID: 16169937. 5: Doggrell SA, Hancox JC. Dronedarone: an amiodarone analogue. Expert Opin Investig Drugs. 2004 Apr;13(4):415-26. doi: 10.1517/13543784.13.4.415. PMID: 15102590. 6: Quaglino D, Ha HR, Duner E, Bruttomesso D, Bigler L, Follath F, Realdi G, Pettenazzo A, Baritussio A. Effects of metabolites and analogs of amiodarone on alveolar macrophages: structure-activity relationship. Am J Physiol Lung Cell Mol Physiol. 2004 Aug;287(2):L438-47. doi: 10.1152/ajplung.00434.2003. Epub 2004 Apr 9. PMID: 15075249. 7: Brandts B, Borchard R, Macianskiene R, Gendviliene V, Dirkmann D, Van Bracht M, Prull M, Meine M, Wickenbrock I, Mubagwa K, Trappe HJ. Inhibition of G protein-coupled and ATP-sensitive potassium currents by 2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran (KB130015), an amiodarone derivative. J Pharmacol Exp Ther. 2004 Jan;308(1):134-42. doi: 10.1124/jpet.103.057646. Epub 2003 Oct 20. PMID: 14569071. 8: Mubagwa K, Macianskiene R, Viappiani S, Gendviliene V, Carlsson B, Brandts B. KB130015, a new amiodarone derivative with multiple effects on cardiac ion channels. Cardiovasc Drug Rev. 2003 Fall;21(3):216-35. doi: 10.1111/j.1527-3466.2003.tb00117.x. PMID: 12931255. 9: Macianskiene R, Bito V, Raeymaekers L, Brandts B, Sipido KR, Mubagwa K. Action potential changes associated with a slowed inactivation of cardiac voltage-gated sodium channels by KB130015. Br J Pharmacol. 2003 Aug;139(8):1469-79. doi: 10.1038/sj.bjp.0705379. PMID: 12922934; PMCID: PMC1573977. 10: Macianskiene R, Viappiani S, Sipido KR, Mubagwa K. Slowing of the inactivation of cardiac voltage-dependent sodium channels by the amiodarone derivative 2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran (KB130015). J Pharmacol Exp Ther. 2003 Jan;304(1):130-8. doi: 10.1124/jpet.102.042218. PMID: 12490583. 11: Carlsson B, Singh BN, Temciuc M, Nilsson S, Li YL, Mellin C, Malm J. Synthesis and preliminary characterization of a novel antiarrhythmic compound (KB130015) with an improved toxicity profile compared with amiodarone. J Med Chem. 2002 Jan 31;45(3):623-30. doi: 10.1021/jm001126+. PMID: 11806713.