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

General Information of Drug (ID: DR1343)
Drug Name
Procainamide hydrochloride
Synonyms
Procainamida; Procainamida [INN-Spanish]; Procainamide [INN:BAN]; Procainamidum; Procainamidum [INN-Latin]; Procainamide (hydrochloride); Procainamide Hcl; Procaine amide hydrochloride; Procainhydrochlorid; Procaini hydrochloridum; Procainii chloridum; Procamide hydrochloride; Procan SR; Procan-SR hydrochloride; Procapan hydrochloride; Procardyl hydrochloride; Promide hydrochloride; Supicane amide hydrochloride; procainamide hydrochloride; 4-amino-N-[2-(diethylamino)ethyl]benzamide hydrochloride; 614-39-1; CCRIS 7143; UNII-SI4064O0LX; Novocamid hydrochloride; Procaine amide; Procamide; Procapan (free base); 4-Amino-N-(2-(diethylamino)ethyl)benzamide; 4-Amino-N-[2-(diethylamino)ethyl]benzamide; 4-amino-N-(2-diethylaminoethyl)benzamide; UNII-L39WTC366D; p-Amino-N-(2-diethylaminoethyl)benzamide; p-Aminobenzoic diethylaminoethylamide; Biocoryl; Novocainamid; Novocainamide; Novocaine amide; Novocamid; PROCAINAMIDE
Indication Ventricular tachyarrhythmia [ICD11: BC71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 271.78 Topological Polar Surface Area 58.4
Heavy Atom Count 18 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
66068
ChEBI ID
CHEBI:8429
CAS Number
614-39-1
TTD Drug ID
D0U5SI
Formula
C13H22ClN3O
Canonical SMILES
CCN(CC)CCNC(=O)C1=CC=C(C=C1)N.Cl
InChI
1S/C13H21N3O.ClH/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11;/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17);1H
InChIKey
ABTXGJFUQRCPNH-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
Desethylprocainamide DM002973
156868
Oxidation - Deethylation 1 [6]
N-acetyl-3-hydroxyprocainamide DM001675
133158
Oxidation - N-Hydroxylation 1 [2] , [6]
Procainamide 4-hydroxylamine DM002974
125600
Oxidation - Hydroxylation 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002156 Procainamide hydrochloride N-Acetyl-3-hydroxyprocainamide Oxidation - N-Hydroxylation CYP2D6 [2], [6]
MR002157 Procainamide hydrochloride Desethylprocainamide Oxidation - Deethylation Unclear [6]
MR002158 Procainamide hydrochloride Procainamide 4-hydroxylamine Oxidation - Hydroxylation Unclear [6]
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]
N-acetyltransferase 1 (NAT1) DME0050 Homo sapiens
ARY1_HUMAN
2.3.1.5
[3]
N-acetyltransferase 2 (NAT2) DME0051 Homo sapiens
ARY2_HUMAN
2.3.1.5
[4]
RNA cytidine acetyltransferase (hALP) DME0007 Homo sapiens
NAT10_HUMAN
2.3.1.5
[5]
References
1 Procainamide Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Involvement of CYP2D6 activity in the N-oxidation of procainamide in man. Pharmacogenetics. 1999 Dec;9(6):683-96.
3 Longitudinal distribution of arylamine N-acetyltransferases in the intestine of the hamster, mouse, and rat. Evidence for multiplicity of N-acetyltransferases in the intestine. Biochem Pharmacol. 1996 Nov 22;52(10):1613-20.
4 Substrate-dependent regulation of human arylamine N-acetyltransferase-1 in cultured cells. Mol Pharmacol. 2000 Mar;57(3):468-73.
5 Effect of H2-receptor antagonists on rat liver cytosolic acetyl CoA:arylamine N-acetyltransferase activity. Drug Metab Dispos. 1992 Jan-Feb;20(1):74-8.
6 Metabolites of procainamide and practolol inhibit complement components C3 and C4 Biochem J. 1988 Apr 15;251(2):323-6. doi: 10.1042/bj2510323.

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