2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole; butanedioic acid

• ChemBase ID: 153936
• Molecular Formular: C22H24N2O4
• Molecular Mass: 380.43696
• Monoisotopic Mass: 380.17360726
• SMILES: c1ccc(cc1)C1(CC1C1=NCCN1)c1ccccc1.C(CC(=O)O)C(=O)O
• Canonical SMILES: c1ccc(cc1)C1(CC1C1=NCCN1)c1ccccc1.OC(=O)CCC(=O)O
• InChI: 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)
• InChIKey: XFUIOIWYMHEPIE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole; butanedioic acid
• IUPAC Traditional name: cibenzoline; succinic acid
• Synonyms: 2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole succinate; Cibenol; Cipralan; Exacor; Cibenzoline succinate; Cibenzoline 琥珀酸盐

Database IDs

• CAS Number: 100678-32-8
• MDL Number: MFCD00941423
• PubChem SID: 24892426; 162248075
• PubChem CID: 57952

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.5896941
• LogD (pH = 7.4): 0.6862473
• Log P: 3.0037708
• Molar Refractivity: 91.4547 cm^3
• Polarizability: 31.341692 Å^3
• Polar Surface Area: 24.39 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥5 mg/mL
• Apperance: white to off-white solid

Safety Information

• RTECS: EJ9960100
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (NMR)
• Empirical Formula (Hill Notation): C18H18N2 ·C4H6O4

DETAILS

Sigma Aldrich - C1618

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.