Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0318)
Drug Name
Cibenzoline
Synonyms
Cibenzolina; Cibenzolina [INN-Spanish]; Cibenzoline; Cibenzoline (INN); Cibenzoline [INN]; Cibenzolinum; Cibenzolinum [INN-Latin]; Cifenline; Cifenline (USAN); Cifenline [USAN]; Ro 22-7796; Ro 227796; UP 33901; (+-)-2-(2,2-Diphenylcyclopropyl)-2-imidazoline; 1H-Imidazole, 2-(2,2-diphenylcyclopropyl)-4,5-dihydro-, (+-)-; 2-(2,2-Diphenyl-cyclopropyl)-4,5-dihydro-1H-imidazole; 2-(2,2-diphenylcyclopropyl)-2-imidazoline; 2-(2,2-diphenylcyclopropyl)-4,5-dihydro-1H-imidazole; 53267-01-9; C18H18N2; CHEMBL87045; EINECS 258-453-7
Indication Atrial fibrillation [ICD11: BC81] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 262.3 Topological Polar Surface Area 24.4
Heavy Atom Count 20 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
2747
ChEBI ID
CHEBI:135083
CAS Number
53267-01-9
Formula
C18H18N2
Canonical SMILES
C1CN=C(N1)C2CC2(C3=CC=CC=C3)C4=CC=CC=C4
InChI
1S/C18H18N2/c1-3-7-14(8-4-1)18(15-9-5-2-6-10-15)13-16(18)17-19-11-12-20-17/h1-10,16H,11-13H2,(H,19,20)
InChIKey
IPOBOOXFSRWSHL-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
2-(2,2-diphenylcyclopropyl)-1H-imidazole DM003160
135070
Unclear 1 [3]
4,5-dehydrocibenzoline DM003157 N. A. Oxidation - Hydrolyzationn 1 [2]
Cibenzoline Metabolite M3 DM003158 N. A. Oxidation - Hydrolyzationn 1 [2]
Cibenzoline Metabolite M4 DM003159 N. A. Oxidation - Hydrolyzationn 1 [2]
p-hydroxycibenzoline DM003156
196604
Oxidation - Hydrolyzationn 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003606 Cibenzoline p-hydroxycibenzoline Oxidation - Hydrolyzationn CYP2D6 [2]
MR003607 Cibenzoline 4,5-dehydrocibenzoline Oxidation - Hydrolyzationn CYP3A4 [2]
MR003608 Cibenzoline Cibenzoline Metabolite M3 Oxidation - Hydrolyzationn CYP3A4 [2]
MR003609 Cibenzoline Cibenzoline Metabolite M4 Oxidation - Hydrolyzationn CYP3A4 [2]
MR003610 Cibenzoline 2-(2,2-diphenylcyclopropyl)-1H-imidazole Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 ClinicalTrials.gov (NCT00540787) A Comparison of Antiarrhythmic Drug Therapy and Radio Frequency Catheter Ablation in Patients With Paroxysmal Atrial Fibrillation.
2 Stereoselective metabolism of cibenzoline, an antiarrhythmic drug, by human and rat liver microsomes: possible involvement of CYP2D and CYP3A. Drug Metab Dispos. 2000 Sep;28(9):1128-34.
3 Biotransformation of cibenzoline to 2-(2,2-diphenylcyclopropyl)-1H-imidazole

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