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

General Information of Drug (ID: DR1361)
Drug Name
Propafenone hydrochloride
Synonyms
Propafenon hydrochlorid; Propafenon hydrochlorid [German]; Propafenone (hydrochloride); Propafenone HCl; Rhythmonorm; Rythmol SR; Rytmonorm; WZ 884; 1-(2-(2-Hydroxy-3-(propylamino)propoxy)phenyl)-3-phenylpropan-1-one hydrochloride; 1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenylpropan-1-one hydrochloride; 1-{2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one hydrochloride; 34183-22-7; EINECS 251-867-9; MLS000069682; SA 79; Arythmol; Baxarytmon; Fenoprain; PROPAFENONE HYDROCHLORIDE; Pronon
Indication Ventricular tachyarrhythmia [ICD11: BC71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 377.9 Topological Polar Surface Area 58.6
Heavy Atom Count 26 Rotatable Bond Count 11
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
36708
ChEBI ID
CHEBI:8466
CAS Number
34183-22-7
TTD Drug ID
D0J2KV
Formula
C21H28ClNO3
Canonical SMILES
CCCNCC(COC1=CC=CC=C1C(=O)CCC2=CC=CC=C2)O.Cl
InChI
1S/C21H27NO3.ClH/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17;/h3-11,18,22-23H,2,12-16H2,1H3;1H
InChIKey
XWIHRGFIPXWGEF-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
(S)-4'-hydroxypropafenone DM003008
154699855
Oxidation - Hydroxylation 1 [4]
(S)-5-hydroxypropafenone DM003006
40565857
Oxidation - Hydroxylation 1 [4]
(S)-N-Despropylpropafenone DM003007
40582745
Oxidation - N-Dealkylation 1 [4]
5-hydroxypropafenone DM003004
107927
Oxidation - 5-Hydroxylation 1 [3] , [5]
N-depropylpropafenone DM003005
128820
Oxidation - N-Dealkylation 1 [3]
Propafenone glucuronide DM003009
185111
Conjugation - Glucuronidation 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002879 Propafenone hydrochloride 5-hydroxypropafenone Oxidation - 5-Hydroxylation CYP2D6 [3], [5]
MR002880 Propafenone hydrochloride N-depropylpropafenone Oxidation - N-Dealkylation CYP1A2 ... [3]
MR002881 Propafenone hydrochloride (S)-5-hydroxypropafenone Oxidation - Hydroxylation CYP2D6 [4]
MR002882 Propafenone hydrochloride (S)-N-Despropylpropafenone Oxidation - N-Dealkylation CYP1A2 ... [4]
MR002883 Propafenone hydrochloride (S)-4'-hydroxypropafenone Oxidation - Hydroxylation CYP2D6 [4]
MR002884 Propafenone hydrochloride Propafenone glucuronide Conjugation - Glucuronidation Unclear [6]
⏷ Show the Full List of 6 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]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Propafenone Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Inhibitory effects of antiarrhythmic drugs on phenacetin O-deethylation catalysed by human CYP1A2. Br J Clin Pharmacol. 1998 Apr;45(4):361-8.
3 Effect of selective serotonin reuptake inhibitors on the oxidative metabolism of propafenone: in vitro studies using human liver microsomes. J Clin Psychopharmacol. 2000 Aug;20(4):428-34.
4 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
5 A rapid HPLC assay for the simultaneous determination of propafenone and its major metabolites in human serum Anal Sci. 2004 Sep;20(9):1307-11. doi: 10.2116/analsci.20.1307.
6 Studies on the metabolism of propafenone. 2nd comm.: studies on the biotransformation in the dog Arzneimittelforschung. 1984;34(9):972-9.

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