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SML2938

Sigma-Aldrich

Vernakalant hydrochloride

≥98% (HPLC)

Synonym(s):

(3R)-1-((1R,2R)-2-(2-(3,4-Dimethoxyphenyl)ethoxy)cyclohexyl)pyrrolidin-3-ol hydrochloride, (3R)-1-[(1R,2R)-2-[2-(3,4-Dimethoxyphenyl)ethoxy]cyclohexyl]-3-pyrrolidinol hydrochloride, RSD 1235, RSD-1235, RSD1235

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About This Item

Empirical Formula (Hill Notation):
C20H31NO4 · HCl
CAS Number:
748810-28-8
Molecular Weight:
385.93
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

InChI

1S/C20H31NO4.ClH/c1-23-19-8-7-15(13-20(19)24-2)10-12-25-18-6-4-3-5-17(18)21-11-9-16(22)14-21;/h7-8,13,16-18,22H,3-6,9-12,14H2,1-2H3;1H/t16-,17-,18-;/m1./s1

InChI key

JMHYCBFEEFHTMK-IIUXMCBISA-N

Biochem/physiol Actions

Vernakalant is a multiple ion channel blocker that exerts in vivo anti-fibrillatory (anti-arrhythmic) efficacy (ED50 = 1.5 μmol/kg/min iv. against ischemia-induced arrhythmias in rats) via atrial-selective Kv1.5 blockage (hKv1.5/rKv4.2/rKv4.3 IC50 = 13/38/30 μM at 1Hz & -80 to 60 mV in 200 (Kv1.5) or 400 (Kv4) msec) as well as potential- and rate-dependent Nav1.5 blockade (inward Na current INa IC50 = 9 μM/20 Hz & -80 mV, 31 μM/1Hz & -60 mV, 107 μM/1Hz & -120 mV using HEK hNav1.5 cells).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Toshiki Chiba et al.
Journal of pharmacological sciences, 130(3), 170-176 (2016-04-02)
Electrical remodeling plays a pivotal role in maintaining the reentry during atrial fibrillation. In this study, we assessed influence of electrical remodeling on pharmacological manipulation of the atrial refractoriness in rabbits. We used an atrial electrical remodeling model of the
Gerrit Frommeyer et al.
Journal of cardiovascular medicine (Hagerstown, Md.), 18(9), 663-668 (2017-07-12)
Current guidelines recommend vernakalant for pharmacologic cardioversion of recent-onset atrial fibrillation. However, this drug is not established as chronic therapy. In total, 15 rabbit hearts were Langendorff-perfused. A burst pacing protocol-induced atrial fibrillation in 7 of 15 hearts at baseline
Jonas Goldin Diness et al.
Circulation. Arrhythmia and electrophysiology, 10(10) (2017-10-12)
Evidence has emerged that small-conductance Ca2+-activated K+ (SK) channels constitute a new target for treatment of atrial fibrillation (AF). SK channels are predominantly expressed in the atria as compared with the ventricles. Various marketed antiarrhythmic drugs are limited by ventricular
Gerrit Frommeyer et al.
Europace : European pacing, arrhythmias, and cardiac electrophysiology : journal of the working groups on cardiac pacing, arrhythmias, and cardiac cellular electrophysiology of the European Society of Cardiology, 19(5), 866-873 (2016-10-06)
The antiarrhythmic drug vernakalant exerts antiarrhythmic effects in atrial fibrillation. Recent experimental data suggest interactions with the late sodium current and antiarrhythmic effects in ventricular arrhythmias. We aimed at investigating whether treatment with vernakalant reduces polymorphic ventricular tachycardia (VT) in
Rong Chen et al.
Biochemistry, 57(18), 2704-2710 (2018-04-14)
Molecular dynamics simulations are employed to determine the inhibitory mechanisms of three drugs, 5-(4-phenoxybutoxy)psoralen (PAP-1), vernakalant, and flecainide, on the voltage-gated K+ channel Kv1.5, a target for the treatment of cardiac arrhythmia. At neutral pH, PAP-1 is neutral, whereas the
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