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

General Information of Drug (ID: DR1072)
Drug Name
Metoprolol tartrate
Synonyms
Metoproferm; Metoprolin; Metoprolol AL; Metoprolol Atid; Metoprolol Basics; Metoprolol PB; Metoprolol Stada; Metoprolol Verla; Metoprolol acis; Metoprolol tartrate; Metoprolol-GRY; Metoprolol-Wolf; Metoprolol-rpm; Prelis; Proken M; Prolaken; Ritmolol; Selectadril; Selokeen; Selopral; Sigaprolol; Slow lopresor; Slow-Lopresor; Topromel; Vasocardin; 56392-17-7; Beloc; Lanoc; Metop; Minax; Apo-Metoprolol; Arbralene; Azumetop; Beprolo; Bloksan; Bloxan; Cardoxone; Jeprolol; Kapodine; Mepolol; Meto-Isis; Metoberag; Metoberta; Metocard; Metolol; Metomerck
Indication Angina pectoris [ICD11: BA40] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 684.8 Topological Polar Surface Area 217
Heavy Atom Count 48 Rotatable Bond Count 21
Hydrogen Bond Donor Count 8 Hydrogen Bond Acceptor Count 14
Cross-matching ID
PubChem CID
441308
ChEBI ID
CHEBI:6906
CAS Number
56392-17-7
TTD Drug ID
D0I2MK
Formula
C34H56N2O12
Canonical SMILES
CC(C)NCC(COC1=CC=C(C=C1)CCOC)O.CC(C)NCC(COC1=CC=C(C=C1)CCOC)O.C(C(C(=O)O)O)(C(=O)O)O
InChI
1S/2C15H25NO3.C4H6O6/c2*1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3;5-1(3(7)8)2(6)4(9)10/h2*4-7,12,14,16-17H,8-11H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t;;1-,2-/m..1/s1
InChIKey
YGULWPYYGQCFMP-CEAXSRTFSA-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 [3]
H104/83 DM004398 N. A. Unclear 1 [5]
H105/22 DM004394
162181
Unclear 1 [5]
O-Demethylmetoprolol DM004396
40561637
Oxidation - O-dealkylation 1 [3]
H107/04 DM004395 N. A. Unclear 2 [5]
H119/72 DM004391 N. A. Unclear 2 [5]
H119/77 DM004392 N. A. Unclear 3 [5]
H119/68 DM004393 N. A. Unclear 4 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004716 Metoprolol tartrate Alpha-Hydroxymetoprolol Oxidation - Hydrolyzationn CYP2D6 [5]
MR004720 Metoprolol tartrate H105/22 Unclear Unclear [5]
MR004722 Metoprolol tartrate O-Demethylmetoprolol Oxidation - O-dealkylation CYP2D6 ... [3]
MR004723 Metoprolol tartrate Deisopropylmetoprolol Oxidation - N-dealkylation CYP2C19 [3]
MR004724 Metoprolol tartrate H104/83 Unclear Unclear [5]
MR004717 Alpha-Hydroxymetoprolol H119/72 Unclear Unclear [5]
MR004721 H105/22 H107/04 Unclear Unclear [5]
MR004718 H119/72 H119/77 Unclear Unclear [5]
MR004719 H119/77 H119/68 Unclear Unclear [5]
⏷ 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
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [4]
References
1 Metoprolol Tartrate 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 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Metabolism of metoprolol in the rat in vitro and in vivo

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