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

KB-130015
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 531993

CAS#: 147030-48-6

Description: 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

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 531993
Name: KB-130015
CAS#: 147030-48-6
Chemical Formula: C18H14I2O4
Exact Mass: 547.90
Molecular Weight: 548.115
Elemental Analysis: C, 39.44; H, 2.57; I, 46.31; O, 11.68

Price and Availability

Size	Price	Availability
5mg	USD 385	2 Weeks
10mg	USD 700	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	10.0	18.24
	Ethanol	10.0	18.24

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:	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.
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.

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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.

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