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C1618

Sigma-Aldrich

Cibenzoline succinate

≥98% (HPLC), solid

Synonym(s):

2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole succinate, Cibenol, Cipralan, Exacor

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About This Item

Empirical Formula (Hill Notation):
C18H18N2 ·C4H6O4
CAS Number:
100678-32-8
Molecular Weight:
380.44
MDL number:
MFCD00941423
UNSPSC Code:
12352200
PubChem Substance ID:
24892426
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated

color

white to brown

solubility

H2O: ≥5 mg/mL

storage temp.

2-8°C

SMILES string

OC(=O)CCC(O)=O.C1CN=C(N1)C2CC2(c3ccccc3)c4ccccc4

InChI

1S/C18H18N2.C4H6O4/c1-3-7-14(8-4-1)18(15-9-5-2-6-10-15)13-16(18)17-19-11-12-20-17;5-3(6)1-2-4(7)8/h1-10,16H,11-13H2,(H,19,20);1-2H2,(H,5,6)(H,7,8)

InChI key

XFUIOIWYMHEPIE-UHFFFAOYSA-N

General description

Cibenzoline also called (±)-2-(2,2-diphenylcyclopropyl)-2-imidazoline succinate, is generally used in stereo combination of R(+) and S(−) forms. It also exhibits anticholinergic activity.. Cibenzoline is known to improve left ventricular diastolic dysfunction by reducing left ventricular pressure gradient.

Biochem/physiol Actions

Cibenzoline is a class IA antiarrhythmic drug. Cibenzoline (μM concentrations) blocks ATP-sensitive K channels in heart and pancreatic cells. Cibenzoline interacts with the channel pore-forming subunit of the K(ATP) channel (Kir6.2) from the cytoplasmic side. Cibenzoline also inhibits the delayed rectifier K current [I(Kr)] in sino-atrial node cells.

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

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

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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Stereoselective metabolism of cibenzoline, an antiarrhythmic drug, by human and rat liver microsomes: possible involvement of CYP2D and CYP3A
Niwa T, et al.
Drug Metabolism and Disposition, 28(9), 1128-1134 (2000)
Perciliz L Tan et al.
Investigative ophthalmology & visual science, 58(3), 1570-1576 (2017-03-11)
Genome-wide association (GWAS) and sequencing studies for AMD have highlighted the importance of coding variants at loci that encode components of the complement pathway. However, assessing the contribution of such alleles to AMD, especially when they are rare, remains coarse
Impact of chronic use of cibenzoline on left ventricular pressure gradient and left ventricular remodeling in patients with hypertrophic obstructive cardiomyopathy
Hamada M, et al.
Journal of Cardiology, 67(3), 279-286 (2016)
Cibenzoline for left ventricular outflow tract obstruction in tako-tsubo cardiomyopathy and hypertrophic cardiomyopathy
Anan R
Journal of Cardiology Cases, 11(6), 158-159 (2015)

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