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

General Information of Drug (ID: DR0550)
Drug Name
Dronedarone hydrochloride
Synonyms
Dronedarone (Hydrochloride); Dronedarone HCl; Dronedarone HCl (Multaq); Dronedarone hydrochloride; Dronedarone hydrochloride [USAN]; Dronedarone; Dronedarone (INN); Dronedarone [INN]; JQZ1L091Y2; Multaq; N-(2-Butyl-3-(p-(3-(dibutylamino)propoxy)benzoyl)-5-benzofuranyl)methanesulfonamide; N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)-5-benzofuranyl)-methanesulfonamide; N-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]-1-benzofuran-5-yl]methanesulfonamide; N-[2-butyl-3-{4-[3-(dibutylamino)propoxy]benzoyl}-1-benzofuran-5-yl]methanesulfonamide; NCGC00188863-01; SR 33589; SR 33589B; SR33589; UNII-JQZ1L091Y2; 141626-36-0; CHEBI:50659; CHEMBL184412; FA36DV299Q; MFCD00914940; N-(2-Butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)-5-benzofuranyl)methanesulfonamide monohydrochloride; N-(2-Butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)methanesulfonamide hydrochloride; N-(2-butyl-3-{4-[3-(dibutylamino)propoxy]benzoyl}-1-benzofuran-5-yl)methanesulfonamide hydrochloride; UNII-FA36DV299Q; 141625-93-6; 4CH-007232
Indication Atrial fibrillation [ICD11: BC81] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 593.2 Topological Polar Surface Area 97.2
Heavy Atom Count 40 Rotatable Bond Count 18
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
219025
CAS Number
141625-93-6
TTD Drug ID
D05CPV
Formula
C31H45ClN2O5S
Canonical SMILES
CCCCC1=C(C2=C(O1)C=CC(=C2)NS(=O)(=O)C)C(=O)C3=CC=C(C=C3)OCCCN(CCCC)CCCC.Cl
InChI
1S/C31H44N2O5S.ClH/c1-5-8-12-29-30(27-23-25(32-39(4,35)36)15-18-28(27)38-29)31(34)24-13-16-26(17-14-24)37-22-11-21-33(19-9-6-2)20-10-7-3;/h13-18,23,32H,5-12,19-22H2,1-4H3;1H
InChIKey
DWKVCQXJYURSIQ-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
C-dealkyl-dronedarone DM006253
10269014
Oxidation - Dealkylation 1 [6]
N-debutyl-dronedarone DM006246
10255437
Oxidation - N-debutylation 1 [6]
Deaminated N,N-didebutyl-dronedarone DM006247
123819008
Multi-steps Reaction - Deamination; debutylation 2 [5]
Phenol-dronedarone DM006249
70653166
Oxidation - O-dealkylation 2 [5]
Deaminated N,N-didebutyl-dronedarone glucuronide DM006248 N. A. Conjugation - Glucuronidation 3 [5]
N,N'-didebutyl-dronedarone DM006252
10095002
Oxidation - Debutylation 3 [5]
Phenol-dronedarone glucuronide DM006250 N. A. Conjugation - Glucuronidation 3 [5]
Propanoic acid-dronedarone DM006251
71495101
Oxidation - Oxidationn deamination 3 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006701 Dronedarone hydrochloride N-debutyl-dronedarone Oxidation - N-debutylation CYP3A4 ... [6]
MR006708 Dronedarone hydrochloride C-dealkyl-dronedarone Oxidation - Dealkylation Unclear [6]
MR006702 N-debutyl-dronedarone Deaminated N,N-didebutyl-dronedarone Multi-steps Reaction - Deamination; debutylation MAOA [5]
MR006704 N-debutyl-dronedarone Phenol-dronedarone Oxidation - O-dealkylation MAOA [5]
MR006706 N-debutyl-dronedarone Propanoic acid-dronedarone Oxidation - Oxidationn deamination MAOA [5]
MR006707 N-debutyl-dronedarone N,N'-didebutyl-dronedarone Oxidation - Debutylation CYP3A4 [5]
MR006703 Deaminated N,N-didebutyl-dronedarone Deaminated N,N-didebutyl-dronedarone glucuronide Conjugation - Glucuronidation UGT2A1 [5]
MR006705 Phenol-dronedarone Phenol-dronedarone glucuronide Conjugation - Glucuronidation UGT1A1 ... [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 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Monoamine oxidase type A (MAO-A) DME0044 Homo sapiens
AOFA_HUMAN
1.4.3.4
[5]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2A1 (UGT2A1) DME0622 Homo sapiens
UD2A1_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME0049 Homo sapiens
UDB15_HUMAN
2.4.1.17
[5]
⏷ Show the Full List of 8  DME(s)
References
1 Dronedarone Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effect of dronedarone on the pharmacokinetics of carvedilol following oral administration to rats. Eur J Pharm Sci. 2018 Jan 1;111:13-19.
3 Drug safety evaluation of dronedarone in atrial fibrillation. Expert Opin Drug Saf. 2012 Nov;11(6):1023-45.
4 Inactivation of human cytochrome P450 3A4 and 3A5 by dronedarone and N-desbutyl dronedarone. Mol Pharmacol. 2016 Jan;89(1):1-13.
5 DrugBank(Pharmacology-Metabolism):Dronedarone hydrochloride
6 Identification of metabolic pathways and enzyme systems involved in the in vitro human hepatic metabolism of dronedarone, a potent new oral antiarrhythmic drug. Pharmacol Res Perspect. 2014 Jun;2(3):e00044.

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