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M5060

Sigma-Aldrich

E-4031

≥98% (HPLC), lyophilized powder

Synonym(s):

N-[4-[[1-[2-(6-Methyl-2-pyridinyl)ethyl]-4-piperidinyl]carbonyl]phenyl]methanesulfonamide dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C21H27N3O3S · 2HCl
CAS Number:
113559-13-0
Molecular Weight:
474.44
MDL number:
MFCD01754739
UNSPSC Code:
12352207
PubChem Substance ID:
329818000
NACRES:
NA.77

Assay

≥98% (HPLC)

form

lyophilized powder

storage condition

desiccated

technique(s)

cell culture | embryo: suitable

color

white

solubility

H2O: soluble

storage temp.

−20°C

SMILES string

Cl.Cl.Cc1cccc(CCN2CCC(CC2)C(=O)c3ccc(NS(C)(=O)=O)cc3)n1

InChI

1S/C21H27N3O3S.2ClH/c1-16-4-3-5-19(22-16)12-15-24-13-10-18(11-14-24)21(25)17-6-8-20(9-7-17)23-28(2,26)27;;/h3-9,18,23H,10-15H2,1-2H3;2*1H

InChI key

ZQBNWMFBOSOOLX-UHFFFAOYSA-N

Application

E-4031 has been used as:
  • human ether-a-go-go-related gene (hERG) blocker in human-induced pluripotent stem cell-derived cardiomyocytes (hiPSC-CMs)
  • IKr blocker in long QT syndrome (LQTS) induced pluripotent stem (iPSCs) embryoid bodies
  • IKr blocker in rat ventricular myocytes

Biochem/physiol Actions

E-4031 is a antiarrhythmic drug and belongs to the class III type. It is a methanesulfonanilide compound and is effective in treating arrhythmia and modulates ventricular fibrillation. E-4031 mediates the prolongation of action potential duration (APD) in transgenic long-QT type 1 (LQT1) rabbits. An isoleucine mutation in human ether-a-go-go-related gene (hERG) abolishes its interaction with E-4031.
E-4031 selectively blocks hERG K+ channels.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Susann Björk et al.
Frontiers in physiology, 8, 884-884 (2017-11-23)
Current cardiac drug safety assessments focus on hERG channel block and QT prolongation for evaluating arrhythmic risks, whereas the optogenetic approach focuses on the action potential (AP) waveform generated by a monolayer of human cardiomyocytes beating synchronously, thus assessing the
Masataka Fujiwara et al.
PloS one, 6(2), e16734-e16734 (2011-03-03)
Induced pluripotent stem cells (iPSCs) are novel stem cells derived from adult mouse and human tissues by reprogramming. Elucidation of mechanisms and exploration of efficient methods for their differentiation to functional cardiomyocytes are essential for developing cardiac cell models and
Dissociation of E-4031 from the HERG channel caused by mutations of an amino acid results in greater block at high stimulation frequency
Ishii K, et al.
Cardiovascular Research, 57(3), 651-659 (2003)
Impaired inactivation of L-Type Ca2+ current as a potential mechanism for variable arrhythmogenic liability of HERG K+ channel blocking drugs
Kim JG, et al.
PLoS ONE, 11(3), e0149198-e0149198 (2016)
Min Li et al.
Journal of pharmacological sciences, 134(2), 75-85 (2017-06-16)
Human induced pluripotent stem cell (hiPSC)-derived cardiomyocytes hold great potentials to predict pro-arrhythmic risks in preclinical cardiac safety screening, although the hiPSC cardiomyocytes exhibit rather immature functional and structural characteristics, including spontaneous activity. Our physiological characterization and mathematical simulation showed
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