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

General Information of Drug (ID: DR1079)
Drug Name
Mexiletine hydrochloride
Synonyms
Mexiletina; Mexiletina [INN-Spanish]; Mexiletine; Mexiletine [INN:BAN]; Mexiletinum; Mexiletinum [INN-Latin]; Mexilitine; Mexityl; VLPIATFUUWWMKC-UHFFFAOYSA-N; 1-(2',6'-Dimethylphenoxy)-2-aminopropane; 1-(2,6-Dimethylphenoxy)-2-propanamine; 1-(2,6-dimethylphenoxy)propan-2-amine; 1-Methyl-2-(2,6-xylyloxy)ethylamine; 2-(2-aminopropoxy)-1,3-dimethylbenzene; 2-Propanamine, 1-(2,6-dimethylphenoxy)-; 31828-71-4; BRN 2092205; CHEBI:6916; CHEMBL558; EINECS 250-825-7; ETHYLAMINE, 1-METHYL-2-(2,6-XYLYLOXY)-; KO1173; KO 1173; Ko 1173 Cl; Mexiletene hydrochloride; Mexiletine (hydrochloride); Mexiletine HCL; Mexiletine hydrochloride; (S)-1-(2,6-Dimethylphenoxy)propan-2-amine hydrochloride; 1-(2,6-Dimethylphenoxy)-2-propanamine hydrochloride; 1-(2,6-Xylyloxy)-2-aminopropane hydrochloride; 1-(2,6-dimethylphenoxy)propan-2-amine hydrochloride; 2-Propanamine, 1-(2,6-dimethylphenoxy)-, hydrochloride; DSSTox_CID_25783; DSSTox_GSID_45783; DSSTox_RID_81125; EINECS 226-362-1; MFCD00216024; NCGC00094121-01
Indication Ventricular tachyarrhythmia [ICD11: BC71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 215.72 Topological Polar Surface Area 35.2
Heavy Atom Count 14 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
21467
ChEBI ID
CHEBI:6917
CAS Number
5370-01-4
TTD Drug ID
D0X0RI
Formula
C11H18ClNO
Canonical SMILES
CC1=C(C(=CC=C1)C)OCC(C)N.Cl
InChI
1S/C11H17NO.ClH/c1-8-5-4-6-9(2)11(8)13-7-10(3)12;/h4-6,10H,7,12H2,1-3H3;1H
InChIKey
NFEIBWMZVIVJLQ-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-hydroxymexiletine DM004409
93285
Oxidation - 2-hydroxylation 1 [6]
M-hydroxy ME DM004413
3035569
Unclear 1 [7]
p-hydroxymexiletine DM004411
93286
Oxidation - Hydrolyzationn 1 [6]
Deamino HMME DM004410
85909061
Unclear 2 [8]
Deamino pHME DM004412
10420209
Unclear 2 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004735 Mexiletine hydrochloride 2-hydroxymexiletine Oxidation - 2-hydroxylation CYP1A2 ... [6]
MR004737 Mexiletine hydrochloride p-hydroxymexiletine Oxidation - Hydrolyzationn CYP1A2 ... [6]
MR004739 Mexiletine hydrochloride M-hydroxy ME Unclear Unclear [7]
MR004736 2-hydroxymexiletine Deamino HMME Unclear Unclear [8]
MR004738 p-hydroxymexiletine Deamino pHME Unclear Unclear [8]
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 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
References
1 Mexiletine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Inhibition of human liver cytochrome P-450 1A2 by the class IB antiarrhythmics mexiletine, lidocaine, and tocainide. J Pharmacol Exp Ther. 1999 May;289(2):853-8.
3 Role of specific cytochrome P450 enzymes in the N-oxidation of the antiarrhythmic agent mexiletine. Xenobiotica. 2003 Jan;33(1):13-25.
4 Impact of CYP2D6*10 on mexiletine pharmacokinetics in healthy adult volunteers. Eur J Clin Pharmacol. 2003 Sep;59(5-6):395-9.
5 Pharmacokinetic and pharmacodynamic interaction between mexiletine and propafenone in human beings. Clin Pharmacol Ther. 2000 Jul;68(1):44-57.
6 Involvement of CYP1A2 in mexiletine metabolism. Br J Clin Pharmacol. 1998 Jul;46(1):55-62.
7 [Thyroid neoplasms and HL-A system]
8 Inhibition kinetics of theophylline metabolism by mexiletine and its metabolites

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