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

General Information of Drug (ID: DR0575)
Drug Name
Encainide
Synonyms
Encainida; Encainida [Spanish]; Encainide; Encainide [French]; Encainide [INN:BAN]; Encainidum; Encainidum [Latin]; Enkaid; MJ 9067; MJ-9067; PJWPNDMDCLXCOM-UHFFFAOYSA-N; (+-)-4-Methoxy-N-(2-(2-(1-methyl-2-piperidinyl)ethyl)phenyl)benzamide; 37612-13-8; 4-Methoxy-N-(2-(2-(1-methylpiperidin-2-yl)ethyl)phenyl)benzamide; 4-methoxy-N-{2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl}benzamide; 66778-36-7; BRN 0497572; Benzamide, 4-methoxy-N-[2-[2-(1-methyl-2-piperidinyl)ethyl]phenyl]-; CHEBI:4788
Indication Cardiac arrhythmia [ICD11: BC65] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 352.5 Topological Polar Surface Area 41.6
Heavy Atom Count 26 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
48041
PubChem SID
9192 ; 6165533 ; 7979158 ; 8180518 ; 12012630 ; 15373859 ; 34712961 ; 46504470 ; 48415942 ; 49877070 ; 50064743 ; 57313176 ; 80562377 ; 96024590 ; 99313642 ; 104354474 ; 117563414 ; 124896651 ; 125749069 ; 126666719 ; 128926702 ; 134223157 ; 134337811 ; 135007178 ; 135049140 ; 137231478 ; 142970991 ; 162518740 ; 163693531 ; 163852995 ; 172892145 ; 179225703 ; 184536609 ; 184547004 ; 194147897 ; 196396473 ; 203084558 ; 223669045 ; 224787244 ; 225384108 ; 226471947 ; 241066723 ; 249965307 ; 252345471
ChEBI ID
CHEBI:4788
CAS Number
66778-36-7
TTD Drug ID
D06PAZ
Formula
C22H28N2O2
Canonical SMILES
CN1CCCCC1CCC2=CC=CC=C2NC(=O)C3=CC=C(C=C3)OC
InChI
1S/C22H28N2O2/c1-24-16-6-5-8-19(24)13-10-17-7-3-4-9-21(17)23-22(25)18-11-14-20(26-2)15-12-18/h3-4,7,9,11-12,14-15,19H,5-6,8,10,13,16H2,1-2H3,(H,23,25)
InChIKey
PJWPNDMDCLXCOM-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
N-desmethylencainide DM006609
48041
Oxidation - Demethylation 1 [3]
O-desmethylencainide DM006606
54736
Oxidation - Demethylation 1 [3] , [4]
3-methoxy-O-desmethylencainide DM006607
54737
Conjugation - Methylationn 2 [3]
N,O-didesmethylencainide DM006608 N. A. Oxidation - Demethylation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007125 Encainide O-desmethylencainide Oxidation - Demethylation CYP2D6 [3], [4]
MR007128 Encainide N-desmethylencainide Oxidation - Demethylation Unclear [3]
MR007129 N-desmethylencainide N,O-didesmethylencainide Oxidation - Demethylation Unclear [3]
MR007126 O-desmethylencainide 3-methoxy-O-desmethylencainide Conjugation - Methylationn Unclear [3]
MR007127 O-desmethylencainide N,O-didesmethylencainide Oxidation - Demethylation 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]
References
1 New antiarrhythmic drugs: tocainide, mexiletine, flecainide, encainide, and amiodarone. Mayo Clin Proc. 1987 Nov;62(11):1033-50.
2 Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Clin Pharmacokinet. 2000 Feb;38(2):111-80.
3 Oxidative metabolism of encainide: polymorphism, pharmacokinetics and clinical considerations
4 Polymorphism of human cytochrome P450 2D6 and its clinical significance: Part I. Clin Pharmacokinet. 2009;48(11):689-723.

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