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

General Information of Drug (ID: DR1607)
Drug Name
Tocainide
Synonyms
Taquidil; Tocainida; Tocainida [INN-Spanish]; Tocainide [USAN:BAN:INN]; Tocainidum; Tocainidum [INN-Latin]; Tonocard; W-36095; Alanyl-2,6-xylidide; Astra W 36095; N-(2,6-dimethylphenyl)alaninamide; tocainide; 2',6'-Propionoxylidide, 2-amino-; 2-AMINO-N-(2,6-DIMETHYLPHENYL)PROPANAMIDE; 2-Amino-2',6'-propionoxylidide; 2-Amino-N-(2,6-dimethylphenyl)propionamid; 41708-72-9; BRN 2416564; C11H16N2O; CHEBI:9611; EINECS 255-505-0; N1-(2,6-dimethylphenyl)alaninamide; Propanamide, 2-amino-N-(2,6-dimethylphenyl)-; SMR000466388
Indication Ventricular tachyarrhythmia [ICD11: BC71] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 192.26 Topological Polar Surface Area 55.1
Heavy Atom Count 14 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
38945
PubChem SID
9351 ; 6596767 ; 7980808 ; 8175799 ; 11467055 ; 11468175 ; 11486810 ; 14797358 ; 26719896 ; 26755668 ; 34704899 ; 46386772 ; 46505385 ; 47207830 ; 47647789 ; 47945105 ; 48095800 ; 48170709 ; 49681729 ; 49699394 ; 50025969 ; 50111018 ; 50209485 ; 56313712 ; 56459344 ; 57312259 ; 85788915 ; 90341559 ; 92308356 ; 92714653 ; 92729958 ; 103990696 ; 104234273 ; 104330445 ; 117572998 ; 119526024 ; 124658847 ; 124800068 ; 125536952 ; 126623963 ; 127569462 ; 134337809 ; 135002146 ; 135111575 ; 135251693 ; 137231400 ; 142472715 ; 145355976 ; 160964390 ; 162022110
ChEBI ID
CHEBI:9611
CAS Number
41708-72-9
TTD Drug ID
D01PJR
Formula
C11H16N2O
Canonical SMILES
CC1=C(C(=CC=C1)C)NC(=O)C(C)N
InChI
1S/C11H16N2O/c1-7-5-4-6-8(2)10(7)13-11(14)9(3)12/h4-6,9H,12H2,1-3H3,(H,13,14)
InChIKey
BUJAGSGYPOAWEI-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
2,6-xylidine DM000340
6896
Hydrolysis - Amide Hydrolysis 1 [3]
Lactoxylidide DM006297
161622
Unclear 1 [4]
Tocainide Carbam Oyl 073-D-Glucuronide DM006292 N. A. Unclear 1 [4]
Tocainide Carbaminic Acid DM006290 N. A. Unclear 1 [5]
Tocainide metabolite M4 DM006294
23553149
Unclear 1 [3]
Tocainide metabolite M5 DM006296 N. A. Unclear 1 [3]
Tocainide metabolite M6 DM006293
3080929
Unclear 2 [3]
TOCG DM006291 N. A. Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006755 Tocainide Tocainide Carbaminic Acid Unclear Unclear [5]
MR006757 Tocainide Tocainide Carbam Oyl 073-D-Glucuronide Unclear Unclear [4]
MR006759 Tocainide Tocainide metabolite M4 Unclear Unclear [3]
MR006760 Tocainide Tocainide metabolite M3 Hydrolysis - Amide Hydrolysis Unclear [3]
MR006761 Tocainide Tocainide metabolite M5 Unclear Unclear [3]
MR006762 Tocainide Lactoxylidide Unclear Unclear [4]
MR006758 Tocainide Carbam Oyl 073-D-Glucuronide Tocainide metabolite M6 Unclear Unclear [3]
MR006756 Tocainide Carbaminic Acid TOCG Unclear Unclear [5]
⏷ Show the Full List of 8 MR(s)
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]
References
1 Tocainide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The effect of tocainide on theophylline metabolism. Br J Clin Pharmacol. 1993 Apr;35(4):437-40.
3 Metabolism of tocainide in the rat
4 On the kinetics and dynamics of tocainide and its metabolites
5 Tocainide kinetics and metabolism: effects of phenobarbital and substrates of glucuronyl transferase

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