General
Preferred name
METOPROLOL
Synonyms
METOPROLOL TARTRATE ()
Metoros ()
Metoros LS ()
CGP-2175C ()
Lopressor ()
(±)-Metoprolol (+)-tartrate ()
Toprol ()
H 93/26 Succinate ()
Tensomex ()
Lopresor Sr ()
Betaloc S.A. ()
Betaloc ()
Beloc Cor ()
Arbralene ()
Mepranix 50 ()
Mepranix 100 ()
Toprol Xl ()
Lopresor ()
Metoprolol (tartrate) ()
Metroprolol succinate ()
Toprol XL ()
Selozok ()
Butanedioic acid ()
CGP 2175E ()
METOPROLOL SUCCINATE ()
Metoprolol-(+,-) (+)-tartrate salt ()
Metoprolol-d6 (tartrate) ()
Metoprolol (Succinate) ()
metoprolol succinate CDT,SCOLR ()
METOPROLOL FUMARATE ()
Seloken-zok ()
Metoprolol hemisuccinate ()
Toprol-XL ()
Kapspargo sprinkle ()
H-93/26 ()
(rs)-metoprolol ()
Lopressidone ()
Seroken ()
Beatrolol ()
Dl-metoprolol ()
CGP-2175 ()
Metoprolol slow release ()
Metoprolol hemitartrate ()
Metropress ()
NSC-757105 ()
Selopral ()
Prelis ()
CGP-2175E ()
Beloc ()
Seloken ()
CGP 2175C ()
P&D ID
PD010136
CAS
56392-17-7
37350-58-6
98418-47-4
55250-54-9
51384-51-1
79985-31-2
Tags
drug
natural product
biased GPCR ligand
available
Approved by
FDA
First approval
1989
1992
1978
Drug Status
investigational
approved
Drug indication
Hypertension
Antihypertensive
Anti-Anginal
Anti-Adrenergic (beta-receptor),Antihypertensive,Antihypertensive
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ROE
Metoprolol is mainly excreted via the kidneys. From the eliminated dose, less than 5% is recovered unchanged.[A175141]
PHARMACODYNAMICS
Administration of metoprolol in normal subjects is widely reported to produce a dose-dependent reduction on heart rate and cardiac output.[A175141] This effect is generated due to a decreased cardiac excitability, cardiac output, and myocardial oxygen demand.[T76] In the case of arrhythmias, metoprolol produces its effect by reducing the slope of the pacemaker potential as well as suppressing the rate of atrioventricular conduction.[T451] The Metoprolol Atherosclerosis Prevention in Hypertensives (MAPHY) trial showed a significant improvement in sudden cardiac death and myocardial infarction when patients were given with metoprolol as compared with diuretics. As well, in clinical trials performed in 1990, metoprolol reduces mortality and re-infarction in 17% of the individuals when administered chronically after an episode of myocardial infarction.[A175141]
HALF-LIFE
The immediate release formulations of metoprolol present a half-life of about 3-7 hours.[A175141]
MOA
Metoprolol is a beta-1-adrenergic receptor inhibitor specific to cardiac cells with negligible effect on beta-2 receptors. This inhibition decreases cardiac output by producing negative chronotropic and inotropic effects without presenting activity towards membrane stabilization nor intrinsic sympathomimetics.[A175141]
TOXICITY
Oral administration of metoprolol to rats presents an LD50 in the range of 3090 to 4670 mg/kg. Cases of overdose have reported bradycardia, hypotension, bronchospasm, and cardiac failure. In the case of an overdose, gastric lavage is recommended followed by specific treatment according to symptoms.[FDA label] Metoprolol is not reported to be carcinogenic nor mutagenic nor to impair fertility. The only event registered is the increase of macrophages in pulmonary alveoli and slight biliary hyperplasia. When metoprolol was given for long periods of time on the highest dose, there was evidence of small benign lung tumors.[FDA label]
METABOLISM
Metoprolol goes through significant first-pass hepatic metabolism which covers around 50% of the administered dose.[A175141] The metabolism of metoprolol is mainly driven by the activity of CYP2D6[A175162] and to a lesser extent due to the activity of CYP3A4. The metabolism of metoprolol is mainly represented by reactions of hydroxylation and O-demethylation.[L5530]
ABSORPTION
When metoprolol is administered orally, it is almost completely absorbed in the gastrointestinal tract.[A175141] The maximum serum concentration is achieved 20 min after intravenous administration and 1-2 hours after oral administration. The bioavailability of metoprolol is of 100% when administered intravenously and when administered orally it presents about 50% for the tartrate derivative and 40% for the succinate derivative.[T274] The absorption of metoprolol in the form of the tartrate derivative is increased by the concomitant administration of food.[T274]
INDICATION
Metoprolol is indicated for the treatment of angina, heart failure, myocardial infarction, atrial fibrillation, atrial flutter and hypertension.[A175141]; ; Some off-label uses of metoprolol include supraventricular tachycardia and thyroid storm.[A175141]; ; All the indications of metoprolol are part of cardiovascular diseases. These conditions correspond to a number of diseases that involve the function of the heart and blood vessels. The underlying causes of these conditions are variable and can be due to genetic disposition, lifestyle decisions such as smoking, obesity, diet, and lack of exercise, and comorbidity with other conditions such as diabetes. The cardiovascular diseases are the leading cause of death on a global scale.[L5533]
TOXICITY
Oral administration of metoprolol to rats presents an LD50 in the range of 3090 to 4670 mg/kg. Cases of overdose have reported bradycardia, hypotension, bronchospasm, and cardiac failure. In the case of an overdose, gastric lavage is recommended followed by specific treatment according to symptoms.[FDA label]; ; Metoprolol is not reported to be carcinogenic nor mutagenic nor to impair fertility. The only event registered is the increase of macrophages in pulmonary alveoli and slight biliary hyperplasia. When metoprolol was given for long periods of time on the highest dose, there was evidence of small benign lung tumors.[FDA label]
ABSORPTION
When metoprolol is administered orally, it is almost completely absorbed in the gastrointestinal tract.[A175141] The maximum serum concentration is achieved 20 min after intravenous administration and 1-2 hours after oral administration. The bioavailability of metoprolol is of 100% when administered intravenously and when administered orally it presents about 50% for the tartrate derivative and 40% for the succinate derivative.[T274]; ; The absorption of metoprolol in the form of the tartrate derivative is increased by the concomitant administration of food.[T274]
DESCRIPTION
The approved drug metoprolol is a racemic mixture of two enantiomers. The structure shown here does not specify stereochemistry and represents the mixture. The two enantiomers are represented by PubChem entries CID 157717 and CID 157716.
(GtoPdb)
INDICATION
Metoprolol is indicated for the treatment of angina, heart failure, myocardial infarction, atrial fibrillation, atrial flutter and hypertension.[A175141] Some off-label uses of metoprolol include supraventricular tachycardia and thyroid storm.[A175141] All the indications of metoprolol are part of cardiovascular diseases. These conditions correspond to a number of diseases that involve the function of the heart and blood vessels. The underlying causes of these conditions are variable and can be due to genetic disposition, lifestyle decisions such as smoking, obesity, diet, and lack of exercise, and comorbidity with other conditions such as diabetes. The cardiovascular diseases are the leading cause of death on a global scale.[L5533]
PHARMACODYNAMICS
Administration of metoprolol in normal subjects is widely reported to produce a dose-dependent reduction on heart rate and cardiac output.[A175141] This effect is generated due to a decreased cardiac excitability, cardiac output, and myocardial oxygen demand.[T76] In the case of arrhythmias, metoprolol produces its effect by reducing the slope of the pacemaker potential as well as suppressing the rate of atrioventricular conduction.[T451]; ; The Metoprolol Atherosclerosis Prevention in Hypertensives (MAPHY) trial showed a significant improvement in sudden cardiac death and myocardial infarction when patients were given with metoprolol as compared with diuretics. As well, in clinical trials performed in 1990, metoprolol reduces mortality and re-infarction in 17% of the individuals when administered chronically after an episode of myocardial infarction.[A175141]
DESCRIPTION
Mixed mGlu2 agonist/ mGlu3 antagonist
(Tocris Bioactive Compound Library)
DESCRIPTION
Selective beta1 antagonist
(Tocriscreen Plus)
DESCRIPTION
Beta1-Adrenoceptor antagonist
(LOPAC library)
DESCRIPTION
Metoprolol succinate is a selective β-adrenoceptor antagonist. It is used in treatment of several diseases of the cardiovascular system. It is a drug used in the treatment of patients suffering from hypertension, coronary heart disease, chronic heart failure and arrhythmia.
(BOC Sciences Bioactive Compounds)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
1
Organisms
1
Compound Sets
34
BiasDB
BOC Sciences Bioactive Compounds
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
DrugMatrix
Enamine BioReference Compounds
Guide to Pharmacology
Ki Database
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
NPC Screening Collection
Other bioactive compounds
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
The Spectrum Collection
Tocris Bioactive Compound Library
Tocriscreen Plus
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
131
Molecular Weight
267.18
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
2
Rotatable Bonds
9
Ring Count
1
Aromatic Ring Count
1
cLogP
1.61
TPSA
50.72
Fraction CSP3
0.6
Chiral centers
1.0
Largest ring
6.0
QED
0.71
QED
0.71
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target Type
7-TM Receptors
Selectivity
beta1
Target
Adrenergic Receptor
??1-adrenergic receptor
??-adrenergic receptor
¦Â-adrenergic receptor
Pathway
GPCR/G protein
Neuronal Signaling
Apoptosis
Primary Target
Adrenergic ?1 Receptors
MOA
Adrenergic Receptor antagonist
Antagonist
Biosynthetic Origin
Alkaloid
Therapeutic Indication
Antihypertensive
Therapeutic Class
Cardiovascular
Antihypertensive Agents
Solubility
10 mM in H2O (free soluble)
Source data
