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

General Information of Drug (ID: DR1071)
Drug Name
Metoprolol succinate
Synonyms
Metohexal; Metoprolol [USAN:INN:BAN]; Metoprololum; Metoprololum [INN-Latin]; Preblok; Presolol; Selo-Zok; Seroken; Spesicor; Spesikor; Beloc- Zok; Metoprolol (Succinate); Metroprolol succinate; Seloken ZOC; Seloken-ZOK; Selozok; Spesicor Dos; Toprol XL; butanedioic acid; succinic acid; (+-)-1-(Isopropylamino)-3-(p-(2-methoxyethyl)phenoxy)-2-propanol succinate (2:1) (salt); 1-(isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol; 2-Propanol, 1-(4-(2-methoxyethyl)phenoxy)-3-((1-methylethyl)amino)-, (+-)-, butanedioate (2:1) (salt); 98418-47-4; H 93/26 succinate; TOPROL-XL; Toprol; dl-Metoprolol; metoprolol; (RS)-Metoprolol; 1-(Isopropylamino)-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol; 37350-58-6; 51384-51-1; CCRIS 4198; CGP 2175; CHEMBL13; HSDB 6531; Beatrolol; Betalok; LOPRESSIDONE; Lopresor; Lopresoretic; Lopressor; Meijoprolol
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 652.8 Topological Polar Surface Area 176
Heavy Atom Count 46 Rotatable Bond Count 21
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
62937
ChEBI ID
CHEBI:6905
CAS Number
98418-47-4
TTD Drug ID
D0I2MK
Formula
C34H56N2O10
Canonical SMILES
CC(C)NCC(COC1=CC=C(C=C1)CCOC)O.CC(C)NCC(COC1=CC=C(C=C1)CCOC)O.C(CC(=O)O)C(=O)O
InChI
1S/2C15H25NO3.C4H6O4/c2*1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3;5-3(6)1-2-4(7)8/h2*4-7,12,14,16-17H,8-11H2,1-3H3;1-2H2,(H,5,6)(H,7,8)
InChIKey
RGHAZVBIOOEVQX-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
Alpha-Hydroxymetoprolol DM004390
114962
Oxidation - Hydrolyzationn 1 [5]
Deisopropylmetoprolol DM004397
92978216
Oxidation - N-dealkylation 1 [6]
H104/83 DM004398 N. A. Unclear 1 [7]
H105/22 DM004394
162181
Unclear 1 [7]
O-Demethylmetoprolol DM004396
40561637
Oxidation - O-dealkylation 1 [6]
H107/04 DM004395 N. A. Unclear 2 [7]
H119/72 DM004391 N. A. Unclear 2 [7]
H119/77 DM004392 N. A. Unclear 3 [7]
H119/68 DM004393 N. A. Unclear 4 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004707 Metoprolol succinate Alpha-Hydroxymetoprolol Oxidation - Hydrolyzationn CYP2D6 [5]
MR004711 Metoprolol succinate H105/22 Unclear Unclear [7]
MR004713 Metoprolol succinate O-Demethylmetoprolol Oxidation - O-dealkylation CYP2D6 ... [6]
MR004714 Metoprolol succinate Deisopropylmetoprolol Oxidation - N-dealkylation CYP2C19 [6]
MR004715 Metoprolol succinate H104/83 Unclear Unclear [7]
MR004708 Alpha-Hydroxymetoprolol H119/72 Unclear Unclear [7]
MR004712 H105/22 H107/04 Unclear Unclear [7]
MR004709 H119/72 H119/77 Unclear Unclear [7]
MR004710 H119/77 H119/68 Unclear Unclear [7]
⏷ Show the Full List of 9 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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
References
1 Metoprolol Succinate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The impact of CYP2D6 mediated drug-drug interaction: a systematic review on a combination of metoprolol and paroxetine/fluoxetine. Br J Clin Pharmacol. 2018 Dec;84(12):2704-2715.
3 Chemical stability-indicating HPLC study of fixed-dosage combination containing metoprolol tartrate and hydrochlorothiazide.
4 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
5 DrugBank(Pharmacology-Metabolism):Metoprolol succinate
6 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
7 Metabolism of metoprolol in the rat in vitro and in vivo

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