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

General Information of Drug (ID: DR0700)
Drug Name
Flecainide acetate
Synonyms
Flecaine; Flecainida; Flecainida [INN-Spanish]; Flecainide [INN:BAN]; Flecainidum; Flecainidum [INN-Latin]; flecainide; (+)-Flecainide; (+-)-Flecainide; 54143-55-4; Benzamide, N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)-; C17H20F6N2O3; CCRIS 313; CHEBI:75984; CHEMBL652; DSSTox_CID_3054; DSSTox_GSID_23054; DSSTox_RID_76854; N-(2-Piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide; N-(piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide; DJBNUMBKLMJRSA-UHFFFAOYSA-N; NCGC00015443-06; FLECAINIDE MONOACETATE; Flecainide (acetate); Flecainide acetate; Flecainide acetate salt; 54143-56-5; CHEBI:5091; EINECS 258-997-5; MFCD00214290; MLS000069675; N-(2-Piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide monoacetate; N-(2-Piperidylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide monoacetate; N-(Piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide monoacetate; R 818; R-818; EN300-51344; SMR000058451; n-(piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide acetate
Indication Ventricular tachyarrhythmia [ICD11: BC71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 474.4 Topological Polar Surface Area 96.9
Heavy Atom Count 32 Rotatable Bond Count 7
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
41022
ChEBI ID
CHEBI:5091
CAS Number
54143-56-5
TTD Drug ID
D03DAP
Formula
C19H24F6N2O5
Canonical SMILES
CC(=O)O.C1CCNC(C1)CNC(=O)C2=C(C=CC(=C2)OCC(F)(F)F)OCC(F)(F)F
InChI
1S/C17H20F6N2O3.C2H4O2/c18-16(19,20)9-27-12-4-5-14(28-10-17(21,22)23)13(7-12)15(26)25-8-11-3-1-2-6-24-11;1-2(3)4/h4-5,7,11,24H,1-3,6,8-10H2,(H,25,26);1H3,(H,3,4)
InChIKey
RKXNZRPQSOPPRN-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
Meta-O-dealkylated flecainide DM000186
134295
Oxidation - Meta-O-Dealkylation 1 [3] , [2]
Meta-O-dealkylated lactam DM000187
10472784
Oxidation - Meta-O-Dealkylation 1 [3] , [2]
Unclear DM009999 N. A. Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001051 Flecainide acetate Meta-O-dealkylated flecainide Oxidation - Meta-O-Dealkylation CYP2D6 ... [3], [2]
MR001052 Flecainide acetate Meta-O-dealkylated lactam Oxidation - Meta-O-Dealkylation CYP2D6 ... [3], [2]
MR001049 Meta-O-dealkylated flecainide . Unclear Unclear [4]
MR001050 Meta-O-dealkylated lactam . Unclear Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
References
1 Flecainide Acetate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Flecainide: current status and perspectives in arrhythmia management. World J Cardiol. 2015 Feb 26;7(2):76-85.
3 Effects of CYP2D6 genotypes on age-related change of flecainide metabolism: involvement of CYP1A2-mediated metabolism. Br J Clin Pharmacol. 2009 Jul;68(1):89-96.
4 Metabolism of flecainide Am J Cardiol. 1984 Feb 27;53(5):41B-51B. doi: 10.1016/0002-9149(84)90501-0.

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