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

General Information of Drug (ID: DR2295)
Drug Name
Acecainide
Synonyms
ACETANILIDE,; Acetylprocainamide; KEECCEWTUVWFCV-UHFFFAOYSA-N; N-Acetyloprokainamid; N-Acetyloprokainamid [Polish]; N-Acetylprocainamide; 32795-44-1; 4'-((2-(Diethylamino)ethyl)carbamoyl)acetanilide; 4-acetamido-N-[2-(diethylamino)ethyl]benzamide; 910Q707V6F; ASL-601; Acecainida; Acecainida [INN-Spanish]; Acecainide [INN]; Acecainide hydrochloride; Acecainidum; Acecainidum [INN-Latin]; Acekainid; Acekainid [Polish]; BRN 2868559; Benzamide, 4-(acetylamino)-N-(2-(diethylamino)ethyl)-; CHEBI:60728; CHEMBL1097; MLS000069490; NAPA; SMR000059070; UNII-910Q707V6F
Indication Cardiac arrhythmia [ICD11: BC65] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 277.36 Topological Polar Surface Area 61.4
Heavy Atom Count 20 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
4342
ChEBI ID
CHEBI:60728
CAS Number
32795-44-1
TTD Drug ID
D04BQR
Formula
C15H23N3O2
Canonical SMILES
CCN(CC)CCNC(=O)C1=CC=C(C=C1)NC(=O)C
InChI
1S/C15H23N3O2/c1-4-18(5-2)11-10-16-15(20)13-6-8-14(9-7-13)17-12(3)19/h6-9H,4-5,10-11H2,1-3H3,(H,16,20)(H,17,19)
InChIKey
KEECCEWTUVWFCV-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
Desethyl-N-acetylprocainamide DM001678
155689
Oxidation - Desethylation 1 [3]
N-acetyl-3-hydroxyprocainamide DM001675
133158
Unclear 1 [3]
N-acetyl-4-aminobenzoic acid DM001679 N. A. Unclear 1 [3]
N-acetyl-4-aminohippuric acid DM001677 N. A. Unclear 1 [3]
N-acetylprocainamide-N-oxide DM001676 N. A. Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000029 Acecainide N-acetyl-3-hydroxyprocainamide Unclear Unclear [3]
MR000030 Acecainide N-acetylprocainamide-N-oxide Unclear Unclear [3]
MR000031 Acecainide N-acetyl-4-aminohippuric acid Unclear Unclear [3]
MR000032 Acecainide Desethyl-N-acetylprocainamide Oxidation - Desethylation Unclear [3]
MR000033 Acecainide N-acetyl-4-aminobenzoic acid Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [2]
References
1 Acecainide (N-acetylprocainamide). A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in cardiac arrhythmias. Drugs. 1990 May;39(5):720-40.
2 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
3 The implications of procainamide metabolism to its induction of lupus Arthritis Rheum. 1981 Aug;24(8):994-1003. doi: 10.1002/art.1780240803.

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