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Merck
CN

C1618

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
NACRES:
NA.77
PubChem Substance ID:
24892426
UNSPSC Code:
12352200
MDL number:
MFCD00941423

Key Documents

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InChI key

XFUIOIWYMHEPIE-UHFFFAOYSA-N

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)

assay

≥98% (HPLC)

form

solid

storage condition

desiccated

color

white to brown

solubility

H2O: ≥5 mg/mL

storage temp.

2-8°C

Quality Level

100

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.
Cibenzoline succinate inhibits ATP-sensitive K+ channels; class IA antiarrhythmic.

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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000477381
0000477383
0000457721
0000457721
0000253418

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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)
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)
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)

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