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SML0353

Sigma-Aldrich

Azimilide dihydrochloride

≥97% (HPLC)

Synonym(s):

1-[[[5-(4-Chlorophenyl)-2-furanyl]methylene]amino]-3-[4-(4-methyl-1-piperazinyl)butyl]-2,4-imidazolidinedione dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C23H28ClN5O3 · 2HCl
CAS Number:
149888-94-8
Molecular Weight:
530.88
UNSPSC Code:
12352200
PubChem Substance ID:
329825356
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 1 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

Cl.Cl.CN1CCN(CCCCN2C(=O)CN(\N=C/c3ccc(o3)-c4cccc(Cl)c4)C2=O)CC1

InChI

1S/C23H28ClN5O3.2ClH/c1-26-11-13-27(14-12-26)9-2-3-10-28-22(30)17-29(23(28)31)25-16-20-7-8-21(32-20)18-5-4-6-19(24)15-18;;/h4-8,15-16H,2-3,9-14,17H2,1H3;2*1H/b25-16-;;

InChI key

SUHOTCCGXXEWJN-DSHYBBOZSA-N

Application

Azimilide dihydrochloride may be used in the electrophysiology experiments with human ether-a-go-go-related gene 1a (HERG1a) subunit.

Biochem/physiol Actions

Azimilide is an inhibitor of human ether-a-go-go-related gene (HERG) channel. It displays a decrease in inhibitory effect in acidic pH conditions.
Azimilide is an investigational class III anti-arrhythmic drug that blocks fast and slow components of the delayed rectifier cardiac potassium channels. It inhibits KV7.1 and KV11.1 potassium channels. Azimilide′s block of K+ currents is relatively selective for IKr over IKs: It potently blocks the rapidly activating component of the delayed rectifier, IKr (IC50 0.4 mM), and inhibits IKs (IC50 3 mM) with nearly 10-fold less potency. At 10 mM, it does not block the inward rectifier K+ current. It blocks (10 mM) the L-type Ca2+ current (ICa) in a use-dependent manner.

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Philippe Chevalier et al.
Journal of cardiovascular pharmacology, 50(6), 629-632 (2007-12-20)
The effects of chronic oral azimilide therapy on the ventricular defibrillation threshold (DFT) during ischemia are unknown. The effects of azimilide on defibrillation efficacy under ischemic condition were investigated in a closed-chest animal model. Azimilide (20 mg/kg/d) was administered orally
Congrong Lin et al.
Cardiology, 108(1), 18-27 (2006-09-09)
Hyperkalemia is a potentially life-threatening disorder frequently occurring in hospitalized patients. The ischemic myocardium releases potassium into the extracellular space which can cause regional hyperkalemia. These changes may modify the effects of anti-arrhythmic drugs acting on the rapid component of
Irina Savelieva et al.
Clinical cardiology, 31(3), 102-108 (2008-04-03)
Antiarrhythmic drugs are an essential tool in the management of atrial fibrillation (AF). Although we are already on the threshold of a large expansion in the use of ablation therapies, these will not, however, be appropriate for all patients, and
S Sharma
The Journal of the Association of Physicians of India, 55 Suppl, 43-46 (2008-03-29)
The treatment of cardiac arrhythmias has undergone a sea change with the advent of catheter ablative procedures (radiofrequency ablation) and use of implantable cardioverter defibrillator (ICD). The antiarrhythmic drugs at times are used to prevent device related arrhythmia rather than
Qian Yang et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 46(1), 12-18 (2011-04-07)
Due to the complicated pathogenesis of cardiac arrhythmia, the safe and effective therapeutic strategies for cardiac arrhythmia remain an urgent medical problems in the recent years. In this paper, we introduced the research practice of anti-arrhythmic agents targeting on potassium
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