Identification

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Name
Metoprolol
Accession Number
DB00264  (APRD00208)
Type
Small Molecule
Groups
Approved, Investigational
Description

Metoprolol is a selective beta-1 blocker commonly employed as the succinate and tartrate derivatives depending if the formulation is designed to be of immediate release or extended release.2,9 The possibility of the generation of these formulations comes from the lower systemic bioavailability of the succinate derivative.5 To this date, it is one of the preferred beta-blockers in general clinical guidelines and it is widely prescribed in the Netherlands, New Zealand, and the US.3 Metoprolol was developed since 1969 by US Pharmaceutical Holdings I and FDA approved in 1978.8

Structure
Thumb
Synonyms
  • (RS)-Metoprolol
  • 1-(isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol
  • DL-metoprolol
  • Metoprolol
External IDs
CGP-2175
Product Ingredients
IngredientUNIICASInChI Key
Metoprolol fumarateIO1C09Z674119637-66-0BRIPGNJWPCKDQZ-WXXKFALUSA-N
Metoprolol succinateTH25PD4CCB98418-47-4RGHAZVBIOOEVQX-UHFFFAOYSA-N
Metoprolol tartrateW5S57Y3A5L56392-17-7YGULWPYYGQCFMP-CEAXSRTFSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Betaloc Durules Tab 200 mgTablet, extended releaseOralAstra Zeneca1980-12-312009-12-15Canada
Betaloc IV Inj 1 mg/mlSolutionIntravenousAstra Zeneca1987-12-312016-05-12Canada
Betaloc Tab 100 mgTabletOralAstra Zeneca1977-12-312009-12-15Canada
Betaloc Tab 50 mgTabletOralAstra Zeneca1978-12-312009-12-15Canada
Co Metoprolol-L Tablets 100mgTabletOralCobalt LaboratoriesNot applicableNot applicableCanada
Co Metoprolol-L Tablets 50mgTabletOralCobalt LaboratoriesNot applicableNot applicableCanada
KapspargoCapsule, extended release100 mg/1OralSun Pharmaceutical Industries Limited2018-03-15Not applicableUs
KapspargoCapsule, extended release50 mg/1OralSun Pharmaceutical Industries Limited2018-03-15Not applicableUs
KapspargoCapsule, extended release25 mg/1OralSun Pharmaceutical Industries Limited2018-03-15Not applicableUs
KapspargoCapsule, extended release200 mg/1OralSun Pharmaceutical Industries Limited2018-03-15Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ag-metoprolol-LTabletOralAngita Pharma Inc.2018-12-27Not applicableCanada
Ag-metoprolol-LTabletOralAngita Pharma Inc.2018-12-27Not applicableCanada
Ag-metoprolol-LTabletOralAngita Pharma Inc.2018-12-27Not applicableCanada
Apo Metoprolol (type L) Tab 50mgTabletOralApotex Corporation1988-12-31Not applicableCanada
Apo Metoprolol Tab 100mgTabletOralApotex Corporation1984-12-31Not applicableCanada
Apo Metoprolol Tab 50mgTabletOralApotex Corporation1984-12-31Not applicableCanada
Apo-metoprololTabletOralApotex Corporation2002-10-08Not applicableCanada
Apo-metoprolol (type L) Tab 100mgTabletOralApotex Corporation1988-12-31Not applicableCanada
Apo-metoprolol SRTablet, extended releaseOralApotex Corporation2007-07-30Not applicableCanada
Apo-metoprolol SRTablet, extended releaseOralApotex Corporation2007-07-30Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
DutoprolMetoprolol succinate (100 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralAstra Zeneca Lp2011-12-302018-10-11Us
DutoprolMetoprolol succinate (25 mg/1) + Hydrochlorothiazide (12.5 mg/1)TabletOralCovis Pharmaceuticals, Inc.2014-07-012017-01-31Us
DutoprolMetoprolol succinate (100 mg/1) + Hydrochlorothiazide (12.5 mg/1)TabletOralConcordia Pharmaceuticals Inc.2014-07-01Not applicableUs
DutoprolMetoprolol succinate (50 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralAstra Zeneca Lp2006-08-282006-08-28Us
DutoprolMetoprolol succinate (50 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralAstra Zeneca Lp2011-12-302018-10-11Us
DutoprolMetoprolol succinate (50 mg/1) + Hydrochlorothiazide (12.5 mg/1)TabletOralConcordia Pharmaceuticals Inc.2014-07-01Not applicableUs
DutoprolMetoprolol succinate (25 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralAstra Zeneca Lp2006-08-282006-08-28Us
DutoprolMetoprolol succinate (25 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralAstra Zeneca Lp2011-12-302018-10-11Us
DutoprolMetoprolol succinate (25 mg/1) + Hydrochlorothiazide (12.5 mg/1)TabletOralConcordia Pharmaceuticals Inc.2014-07-01Not applicableUs
DutoprolMetoprolol succinate (100 mg/1) + Hydrochlorothiazide (12.5 mg/1)TabletOralCovis Pharmaceuticals, Inc.2014-07-012017-02-28Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
HypertensololMetoprolol tartrate (50 mg/1) + L-Arginine (90 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUs
International/Other Brands
Corvitol (Berlin-Chemie AG / Menarini Group) / Minax (Alphapharm Pty Limited) / Selokeen (AstraZeneca) / TOPROL-XL (Lanett Company, Inc)
Categories
UNII
GEB06NHM23
CAS number
51384-51-1
Weight
Average: 267.3639
Monoisotopic: 267.183443671
Chemical Formula
C15H25NO3
InChI Key
IUBSYMUCCVWXPE-UHFFFAOYSA-N
InChI
InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3
IUPAC Name
1-[4-(2-methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol
SMILES
COCCC1=CC=C(OCC(O)CNC(C)C)C=C1

Pharmacology

Indication

Metoprolol is indicated for the treatment of angina, heart failure, myocardial infarction, atrial fibrillation, atrial flutter and hypertension.1

Some off-label uses of metoprolol include supraventricular tachycardia and thyroid storm.1

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.10

Associated Conditions
Pharmacodynamics

Administration of metoprolol in normal subjects is widely reported to produce a dose-dependent reduction on heart rate and cardiac output.1 This effect is generated due to a decreased cardiac excitability, cardiac output, and myocardial oxygen demand.6 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.7

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.1

Mechanism of action

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.1

TargetActionsOrganism
ABeta-1 adrenergic receptor
antagonist
Humans
NBeta-2 adrenergic receptor
antagonist
Humans
Additional Data Available
Adverse Effects

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

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Absorption

When metoprolol is administered orally, it is almost completely absorbed in the gastrointestinal tract.1 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.5

The absorption of metoprolol in the form of the tartrate derivative is increased by the concomitant administration of food.5

Volume of distribution

The reported volume of distribution of metoprolol is 4.2 L/kg.5 Due to the characteristics of metoprolol, this molecule is able to cross the blood-brain barrier and even 78% of the administered drug can be found in cerebrospinal fluid.11

Protein binding

Metoprolol is not highly bound to plasma proteins and only about 11% of the administered dose is found bound. It is mainly bound to serum albumin.1

Metabolism

Metoprolol goes through significant first-pass hepatic metabolism which covers around 50% of the administered dose.1 The metabolism of metoprolol is mainly driven by the activity of CYP2D63 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.9

Route of elimination

Metoprolol is mainly excreted via the kidneys. From the eliminated dose, less than 5% is recovered unchanged.1

Half life

The immediate release formulations of metoprolol present a half-life of about 3-7 hours.1

Clearance

The reported clearance rate on patients with normal kidney function is 0.8 L/min. In cirrhotic patients, the clearance rate changes to 0.61 L/min.4

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.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.Label

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Metoprolol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Beta-1 adrenergic receptor---(A;A)A AlleleEffect Directly StudiedPatients with this genotype have a greater reduction in blood pressure with metoprolol.Details
Cytochrome P450 2D6CYP2D6*4(A;A)A alleleDirectly Studied EffectPatients with this genotype have reduced metabolism of metoprolol.Details
Beta-1 adrenergic receptor---(C;C) / (C;G)G > CEffect Directly StudiedPatients with this genotype have a greater reduction in blood pressure with metoprolol.Details
Cytochrome P450 2D6CYP2D6*3Not AvailableC alleleADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*6Not Available1707delTADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*7Not Available2935A>CADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*8Not Available1758G>TADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*11Not Available883G>CADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*12Not Available124G>AADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*14ANot Available1758G>AADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*20Not Available1973_1974insGADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*21Not Available2573insCADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all ADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all ADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2ADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*44Not Available2950G>CADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all ADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all ADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*56Not Available3201C>TADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all ADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*62Not Available4044C>TADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all ADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.ADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all ADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*92Not Available1995delCADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all ADR InferredIncreased risk of slow heart rate (bradycardia)Details
Cytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all ADR InferredIncreased risk of slow heart rate (bradycardia)Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Metoprolol.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Metoprolol.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Metoprolol can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Metoprolol.
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Metoprolol.
1,10-Phenanthroline1,10-Phenanthroline may increase the bradycardic activities of Metoprolol.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Metoprolol.
2,5-Dimethoxy-4-ethylamphetamineThe therapeutic efficacy of Metoprolol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of Metoprolol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
25-desacetylrifapentineThe metabolism of Metoprolol can be increased when combined with 25-desacetylrifapentine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
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Food Interactions
  • Avoid alcohol.
  • Avoid natural licorice.
  • Take with food.

References

Synthesis Reference
US3998790
General References
  1. Morris J, Dunham A: Metoprolol . [PubMed:30422518]
  2. Silberstein SD: Preventive Migraine Treatment. Continuum (Minneap Minn). 2015 Aug;21(4 Headache):973-89. doi: 10.1212/CON.0000000000000199. [PubMed:26252585]
  3. Bahar MA, Kamp J, Borgsteede SD, Hak E, Wilffert B: 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. doi: 10.1111/bcp.13741. Epub 2018 Sep 24. [PubMed:30248178]
  4. Regardh CG, Jordo L, Ervik M, Lundborg P, Olsson R, Ronn O: Pharmacokinetics of metoprolol in patients with hepatic cirrhosis. Clin Pharmacokinet. 1981 Sep-Oct;6(5):375-88. doi: 10.2165/00003088-198106050-00004. [PubMed:7333059]
  5. Frishman W., Cheng-Lai A. and Nawarskas J. (2005). Current cardiovascular drugs (4th ed.). Current medicine LLC. [ISBN:1-57340-221-4]
  6. Jones & Bartlett (2016). 2016 Nurse's drug handbook (15th ed.). Jones and Bartlett Publishers Inc..
  7. Saeb-Parsy K., Assomull R., Khan F., Saeb-Parsy K. and Kelly A. (1990). Instant Pharmacology. Willey. [ISBN:0-471-98598-8]
  8. FDA approvals [Link]
  9. Researchgate publications [Link]
  10. Heart [Link]
  11. FDA reports [Link]
External Links
Human Metabolome Database
HMDB0001932
KEGG Drug
D02358
KEGG Compound
C07202
PubChem Compound
4171
PubChem Substance
46506211
ChemSpider
4027
BindingDB
25756
ChEBI
6904
ChEMBL
CHEMBL13
Therapeutic Targets Database
DAP000481
PharmGKB
PA450480
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Metoprolol
ATC Codes
C07FB02 — Metoprolol and felodipineC07FX05 — Metoprolol and ivabradineC07FX03 — Metoprolol and acetylsalicylic acidC07FB13 — Metoprolol and amlodipineC07AB02 — MetoprololC07BB52 — Metoprolol and thiazides, combinationsC07CB02 — Metoprolol and other diureticsC07BB02 — Metoprolol and thiazides
AHFS Codes
  • 24:24.00 — Beta-adrenergic Blocking Agents
FDA label
Download (69.4 KB)
MSDS
Download (43.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic SciencePharmacokinetic Profile / Plasma Concentrations1
0Unknown StatusTreatmentChronic Stable Angina Pectoris1
1CompletedNot AvailableHealthy Volunteers4
1CompletedNot AvailableHealthy Volunteers / Pharmacokinetics of Mirabegron1
1CompletedNot AvailableNonvalvular Atrial Fibrillation1
1CompletedBasic ScienceAcute Myocardial Infarction (AMI)1
1CompletedBasic ScienceAtopic Dermatitis (AD)1
1CompletedBasic ScienceDrug Biotransformation / Membrane Transport1
1CompletedBasic ScienceDrug Drug Interaction (DDI)1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedDiagnosticCytochrome / Pharmacokinetics1
1CompletedOtherHealthy Male Subjects1
1CompletedOtherHealthy Volunteers1
1CompletedSupportive CareHealthy Volunteers1
1CompletedTreatmentFasting2
1CompletedTreatmentFed1
1CompletedTreatmentHealthy Volunteers4
1CompletedTreatmentHigh Blood Pressure (Hypertension)2
1CompletedTreatmentHigh Blood Pressure (Hypertension) / Peripheral Artery Disease (PAD)1
1CompletedTreatmentPlasmodium Infections1
1CompletedTreatmentPsoriasis1
1CompletedTreatmentTumors, Solid1
1CompletedTreatmentType 2 Diabetes Mellitus2
1Not Yet RecruitingOtherHealthy Volunteers1
1RecruitingTreatmentAtopic Dermatitis (AD)1
1RecruitingTreatmentPhase 11
1TerminatedTreatmentHeart Diseases / Heart Valve Disease / Mitral Valve Insufficiency1
1WithdrawnTreatmentHealthy Volunteers1
1, 2RecruitingTreatmentHematologial Malignancy / Tumors, Solid1
1, 2WithdrawnTreatmentDiabetic Macular Edema (DME)1
2Active Not RecruitingTreatmentType 2 Diabetes Mellitus1
2CompletedPreventionCancer, Breast / Heart Failure1
2CompletedTreatmentAging / Cognitive Impairments / High Blood Pressure (Hypertension)1
2CompletedTreatmentCardiovascular Disease (CVD) / Heart Diseases / High Blood Pressure (Hypertension) / Vascular Diseases1
2CompletedTreatmentCurrent or Recent History of Atrial Fibrillation1
2CompletedTreatmentDiastolic Heart Failure1
2RecruitingOtherHealthy Volunteers / Pre Hypertension1
2RecruitingTreatmentAcute Coronary Syndromes (ACS) / Arterial Hypertension1
2RecruitingTreatmentAnterior Myocardial Infarction / Heart Failure1
2RecruitingTreatmentHypertrophic Cardiomyopathy1
2RecruitingTreatmentInfants, Premature1
2RecruitingTreatmentPrader-Willi Syndrome1
2TerminatedTreatmentBMI >30 kg/m21
2TerminatedTreatmentCardiac Arrest / Sudden Cardiac Death / Ventricular Fibrillation / Ventricular Tachycardia (VT)1
2Unknown StatusBasic SciencePostural Orthostatic Tachycardia Syndrome (POTS)1
2Unknown StatusTreatmentAgeing / Cardiovascular Disease (CVD) / Trauma, Multiple1
2, 3Active Not RecruitingTreatmentMinor burns1
2, 3CompletedPreventionDiabetes Mellitus (DM) / High Blood Pressure (Hypertension)1
2, 3CompletedTreatmentB Thalassemia1
2, 3CompletedTreatmentMitral Valve Insufficiency1
2, 3RecruitingTreatmentHigh Blood Pressure (Hypertension)1
2, 3RecruitingTreatmentHigh Blood Pressure (Hypertension) / Sleep Apnea Syndrome1
2, 3RecruitingTreatmentArrhythmia of ventricular origin1
2, 3RecruitingTreatmentMinor burns3
2, 3WithdrawnTreatmentHigh Blood Pressure (Hypertension)1
2, 3WithdrawnTreatmentNonvalvular Atrial Fibrillation / Recurrences1
3Active Not RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3Active Not RecruitingTreatmentHeart Diseases1
3CompletedPreventionAtherosclerosis / Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / High Blood Pressure (Hypertension) / High Cholesterol / Type 2 Diabetes Mellitus1
3CompletedPreventionAtrial Flutter / Nonvalvular Atrial Fibrillation1
3CompletedPreventionLung Cancers / Nonvalvular Atrial Fibrillation1
3CompletedTreatmentBMI >30 kg/m2 / High Blood Pressure (Hypertension)1
3CompletedTreatmentCardiac Remodeling / Cirrhotic Cardiomyopathy / Liver Cirrhosis1
3CompletedTreatmentCongestive Heart Failure (CHF)1
3CompletedTreatmentHigh Blood Pressure (Hypertension)6
3CompletedTreatmentHigh Blood Pressure (Hypertension) / Peripheral Artery Disease (PAD)1
3CompletedTreatmentNonvalvular Atrial Fibrillation1
3CompletedTreatmentPrimary Arterial Hypertension1
3Not Yet RecruitingTreatmentAcute Coronary Syndromes (ACS) / Ischaemic Heart Diseases / Revascularization1
3TerminatedPreventionCardiovascular Disease (CVD)1
3TerminatedTreatmentCongestive Heart Failure (CHF)1
3TerminatedTreatmentHeart Failure, Congestive and Microalbuminuria / High Blood Pressure (Hypertension) / Microalbuminuria1
3TerminatedTreatmentHeart Failure / Nonvalvular Atrial Fibrillation1
3TerminatedTreatmentHigh Blood Pressure (Hypertension)1
3Unknown StatusTreatmentHeart Failure1
3Unknown StatusTreatmentHigh Blood Pressure (Hypertension)1
3WithdrawnTreatmentCancer, Breast1
4Active Not RecruitingBasic ScienceBlood Pressures1
4Active Not RecruitingPreventionAdrenergic Beta-Receptor Blockader / Cardiomyopathy, Post-surgical / Troponin Levels1
4CompletedNot AvailableAcute Coronary Syndromes (ACS)1
4CompletedBasic ScienceBlood Pressures / Drug Overdose / Overdose of Beta-adrenergic Blocking Drug1
4CompletedBasic ScienceIdiopathic Dilated Cardiomyopathy1
4CompletedBasic ScienceMetabolic Syndromes1
4CompletedDiagnosticDiabetes Mellitus (DM)1
4CompletedDiagnosticHigh Blood Pressure (Hypertension)2
4CompletedHealth Services ResearchJNC 7 Stage 1 or 2 Hypertension1
4CompletedOtherHigh Blood Pressure (Hypertension) / Prehypertension2
4CompletedOtherPolyps, Nasal1
4CompletedPreventionBeta Blocker / Endothelial Function1
4CompletedPreventionGraves´ Disease1
4CompletedPreventionHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4CompletedPreventionNonvalvular Atrial Fibrillation / Surgery, Cardiac1
4CompletedSupportive CareHigh Blood Pressure (Hypertension)1
4CompletedTreatmentAcute Myocardial Infarction (AMI)1
4CompletedTreatmentAdverse Effect of Beta-adrenoreceptor Antagonists / Asthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)1
4CompletedTreatmentAngina Pectoris1
4CompletedTreatmentAortic Valve Insufficiency1
4CompletedTreatmentCongestive Cardiomyopathy1
4CompletedTreatmentHeart Failure / Ventricular Dysfunction, Left1
4CompletedTreatmentHeart Rate and Rhythm Disorders1
4CompletedTreatmentHeart Valve Diseases1
4CompletedTreatmentHigh Blood Pressure (Hypertension)12
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4CompletedTreatmentHypertension,Essential2
4CompletedTreatmentMyocardial Infarction1
4CompletedTreatmentRapid Ventricular Response Atrial Fibrillation1
4Not Yet RecruitingTreatmentAcute Myocardial Infarction (AMI) / Non-ST Elevation Myocardial Infarction (NSTEMI) / ST Elevation Myocardial Infarction1
4Not Yet RecruitingTreatmentCoronary Artery Disease2
4Not Yet RecruitingTreatmentNonvalvular Atrial Fibrillation1
4RecruitingBasic ScienceAcute Coronary Syndromes (ACS)1
4RecruitingOtherInterstitial Cystitis/Painful Bladder Syndrome / Myofascial Pelvic Pain1
4RecruitingTreatmentAcute Myocardial Infarction (AMI) / Non-ST Elevation Myocardial Infarction / ST Elevation Myocardial Infarction1
4RecruitingTreatmentAtrial Flutter / Nonvalvular Atrial Fibrillation1
4RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentMyocardial Infarction1
4RecruitingTreatmentNonvalvular Atrial Fibrillation / Permanent Atrial Fibrillation1
4RecruitingTreatmentSyncope, Vasovagal1
4TerminatedPreventionCardiovascular Disease (CVD) / Osteoarthritis (OA)1
4TerminatedPreventionProphylaxis of cardiomyopathy1
4TerminatedTreatmentAnginal Pain / Cardiac Diseases / High Blood Pressure (Hypertension) / Vascular Diseases1
4TerminatedTreatmentCongestive Heart Failure (CHF)1
4TerminatedTreatmentHigh Blood Pressure (Hypertension)3
4Unknown StatusNot AvailableDiabetes Mellitus (DM) / Endothelial Function / High Blood Pressure (Hypertension)1
4Unknown StatusDiagnosticCoronary Artery Disease1
4Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension) / Sexual Dysfunctions1
4WithdrawnBasic ScienceBlood Pressures1
4WithdrawnBasic ScienceCentral Arterial Pressure1
4WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD) / Heart Failure1
Not AvailableActive Not RecruitingTreatmentNonvalvular Atrial Fibrillation1
Not AvailableCompletedNot AvailableHeart Failure / Nonvalvular Atrial Fibrillation1
Not AvailableCompletedNot AvailableHeart Rate Variability / High Blood Pressure (Hypertension) / Tachycardia1
Not AvailableCompletedNot AvailableHemodialysis Treatment / Pharmacokinetics1
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension)2
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension) / Multiple System Atrophy (MSA) / Progressive autonomic failure1
Not AvailableCompletedPreventionAtherosclerosis / Cardiovascular Disease (CVD) / Cerebral Arteriosclerosis / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / Heart Diseases / High Blood Pressure (Hypertension)1
Not AvailableCompletedPreventionCoronary Heart Disease (CHD) / Nonvalvular Atrial Fibrillation1
Not AvailableCompletedTreatmentCVA (Cerebrovascular Accident) / Intracerebral Hemorrhage / Intracranial Hemorrhages1
Not AvailableCompletedTreatmentChronic Heart Failure (CHF) / Nonvalvular Atrial Fibrillation1
Not AvailableCompletedTreatmentFemale Sexual Dysfunction (FSD) / High Blood Pressure (Hypertension)1
Not AvailableCompletedTreatmentHeart Failure1
Not AvailableCompletedTreatmentHigh Blood Pressure (Hypertension) / Plasma Renin Activity1
Not AvailableCompletedTreatmentSyncope, Vasovagal1
Not AvailableRecruitingNot AvailableObesity, Morbid1
Not AvailableRecruitingOtherCoronary Artery Atherosclerosis1
Not AvailableRecruitingSupportive CareCT Angiography / Heart Failure / Heart Failure, Diastolic / Heart Failure, Systolic / Heart Failure,Congestive / Heart Rate Low / Ischaemic Cardiomyopathy / Non-ischaemic Cardiomyopathy1
Not AvailableRecruitingTreatmentAcute Coronary Syndromes (ACS)1
Not AvailableRecruitingTreatmentDrug Absorption1
Not AvailableRecruitingTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableRecruitingTreatmentNonvalvular Atrial Fibrillation1
Not AvailableTerminatedTreatmentHigh Blood Pressure (Hypertension)2
Not AvailableTerminatedTreatmentHigh Blood Pressure (Hypertension) / Transplant; Failure, Kidney1
Not AvailableUnknown StatusNot AvailableHeart Failure1
Not AvailableUnknown StatusNot AvailableHigh Blood Pressure (Hypertension)1
Not AvailableUnknown StatusNot AvailableMyocardial Ischemia1
Not AvailableWithdrawnNot AvailableCardiac Event Risk1
Not AvailableWithdrawnPreventionMyocardial Ischemia1
Not AvailableWithdrawnTreatmentCentral Aortic Pressure1
Not AvailableWithdrawnTreatmentVentricular Tachycardia (VT)1

Pharmacoeconomics

Manufacturers
  • Novartis pharmaceuticals corp
  • Kv pharmaceutical co
  • Sandoz inc
  • Watson laboratories inc florida
  • Wockhardt ltd
  • Astrazeneca lp
  • Bedford laboratories
  • Hikma farmaceutica (portugal) sa
  • Hospira inc
  • Luitpold pharmaceuticals inc
  • Sagent strides llc
  • Sandoz canada inc
  • Watson laboratories inc
  • Apothecon inc div bristol myers squibb
  • Aurobindo pharma ltd
  • Caraco pharmaceutical laboratories ltd
  • Ipca laboratories ltd
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Purepac pharmaceutical co
  • Solco healthcare us llc
  • Teva pharmaceuticals usa inc
  • Teva pharmaceuticals usa
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apothecon
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Astra Pharma Inc.
  • AstraZeneca Inc.
  • Atlantic Biologicals Corporation
  • Aurobindo Pharma Ltd.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Boca Pharmacal
  • Bryant Ranch Prepack
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • Caremark LLC
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Coupler Enterprises Inc.
  • Dept Health Central Pharmacy
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Emcure Pharmaceuticals Ltd.
  • Eon Labs
  • Ethex Corp.
  • General Injectables and Vaccines Inc.
  • Golden State Medical Supply Inc.
  • Greenstone LLC
  • Heartland Repack Services LLC
  • Hikma Pharmaceuticals
  • Hospira Inc.
  • Ipca Laboratories Ltd.
  • Kaiser Foundation Hospital
  • KV Pharmaceutical Co.
  • Lake Erie Medical and Surgical Supply
  • Legacy Pharmaceuticals Packaging LLC
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medisca Inc.
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mutual Pharmaceutical Co.
  • Mylan
  • Neighborcare Repackaging Inc.
  • Novartis AG
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Qualitest
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sagent Pharmaceuticals
  • Sandhills Packaging Inc.
  • Sandoz
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Stat Scripts LLC
  • Talbert Medical Management Corp.
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • Va Cmop Dallas
  • Vangard Labs Inc.
  • Veratex Corp.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
  • Wockhardt Ltd.
Dosage forms
FormRouteStrength
Tablet, film coatedOral
KitOral
TabletOral
Tablet, extended releaseOral
TabletOral100 mg
TabletOral50 mg
Capsule, extended releaseOral100 mg/1
Capsule, extended releaseOral200 mg/1
Capsule, extended releaseOral25 mg/1
Capsule, extended releaseOral50 mg/1
TabletOral200 mg/1
Tablet, coatedOral100 mg/1
Tablet, coatedOral200 mg/1
Tablet, coatedOral25 mg/1
Tablet, coatedOral50 mg/1
Tablet, extended releaseOral100 mg/1
Tablet, extended releaseOral200 mg/1
Tablet, extended releaseOral25 mg/1
Tablet, extended releaseOral50 mg/1
Tablet, film coated, extended releaseOral100 mg/1
Tablet, film coated, extended releaseOral200 mg/1
Tablet, film coated, extended releaseOral25 mg/1
Tablet, film coated, extended releaseOral25 mg/301
Tablet, film coated, extended releaseOral50 mg/301
Tablet, film coated, extended releaseOral50 mg/1
Tablet, film coated, extended releaseOral190 mg/1
Tablet, film coated, extended releaseOral23.75 mg/1
Tablet, film coated, extended releaseOral47.5 mg/1
Tablet, film coated, extended releaseOral90 mg/1
InjectionIntravenous1 mg/1mL
InjectionIntravenous5 mg/5mL
Injection, solutionIntravenous1 mg/1mL
Injection, solutionIntravenous5 mg/5mL
PowderNot applicable1 g/1g
TabletOral100 mg/1
TabletOral25 mg/1
TabletOral50 mg/1
Tablet, film coatedOral100 1/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral37.5 mg/1
Tablet, film coatedOral50 mg/1
Tablet, film coatedOral75 mg/1
TabletOral
SolutionIntravenous
Prices
Unit descriptionCostUnit
Metoprolol tartrate powder5.51USD g
Lopressor 5 mg/5 ml ampul3.85USD ml
Lopressor hct 100-25 tablet3.21USD tablet
Toprol XL 200 mg 24 Hour tablet3.08USD tablet
Lopressor HCT 100-50 mg tablet3.06USD tablet
Toprol xl 200 mg tablet2.96USD tablet
Lopressor hct 100-50 tablet2.82USD tablet
Lopressor 100 mg tablet2.75USD tablet
Metoprolol Succinate 200 mg 24 Hour tablet2.62USD tablet
Metoprolol succ er 200 mg tablet2.29USD tablet
Lopressor HCT 100-25 mg tablet2.21USD tablet
Lopressor HCT 50-25 mg tablet2.14USD tablet
Lopressor hct 50-25 tablet2.06USD tablet
Toprol XL 100 mg 24 Hour tablet1.93USD tablet
Toprol xl 100 mg tablet1.86USD tablet
Lopressor 50 mg tablet1.81USD tablet
Metoprolol Succinate 100 mg 24 Hour tablet1.53USD tablet
Metoprolol succ er 100 mg tablet1.44USD tablet
Toprol XL 25 mg 24 Hour tablet1.43USD tablet
Toprol XL 50 mg 24 Hour tablet1.43USD tablet
Lopresor 1 mg/ml1.29USD ml
Toprol xl 25 mg tablet1.24USD tablet
Toprol xl 50 mg tablet1.24USD tablet
Metoprolol Succinate 25 mg 24 Hour tablet1.17USD tablet
Metoprolol Succinate 50 mg 24 Hour tablet1.13USD tablet
Metoprolol succ er 50 mg tablet0.9USD tablet
Metoprolol succ er 25 mg tablet0.87USD tablet
Metoprolol tartrate 100 mg tablet0.8USD tablet
Toprol xl 100 mg tablet sa0.8USD tablet
Lopresor 100 mg Tablet0.61USD tablet
Lopresor Sr 200 mg Sustained-Release Tablet0.61USD tablet
Metoprolol tartrate 50 mg tablet0.56USD tablet
Metoprolol tartrate 25 mg tablet0.34USD tablet
Apo-Metoprolol Sr 200 mg Sustained-Release Tablet0.34USD tablet
Lopresor Sr 100 mg Sustained-Release Tablet0.34USD tablet
Sandoz Metoprolol Sr 200 mg Sustained-Release Tablet0.34USD tablet
Lopresor 50 mg Tablet0.3USD tablet
Apo-Metoprolol (Type L) 100 mg Tablet0.23USD tablet
Apo-Metoprolol 100 mg Tablet0.23USD tablet
Mylan-Metoprolol (Type L) 100 mg Tablet0.23USD tablet
Novo-Metoprol (Fc) 100 mg Tablet0.23USD tablet
Novo-Metoprol 100 mg Tablet0.23USD tablet
Nu-Metop 100 mg Tablet0.23USD tablet
Pms-Metoprolol-L 100 mg Tablet0.23USD tablet
Sandoz Metoprolol (Type L) 100 mg Tablet0.23USD tablet
Apo-Metoprolol Sr 100 mg Sustained-Release Tablet0.19USD tablet
Sandoz Metoprolol Sr 100 mg Sustained-Release Tablet0.19USD tablet
Apo-Metoprolol (Type L) 50 mg Tablet0.13USD tablet
Apo-Metoprolol 50 mg Tablet0.13USD tablet
Mylan-Metoprolol (Type L) 50 mg Tablet0.13USD tablet
Novo-Metoprol (Fc) 50 mg Tablet0.13USD tablet
Novo-Metoprol 50 mg Tablet0.13USD tablet
Nu-Metop 50 mg Tablet0.13USD tablet
Pms-Metoprolol-L 50 mg Tablet0.13USD tablet
Sandoz Metoprolol (Type L) 50 mg Tablet0.13USD tablet
Apo-Metoprolol 25 mg Tablet0.07USD tablet
Pms-Metoprolol-L 25 mg Tablet0.07USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US9700530No2017-07-112035-07-09Us
US9504655No2016-11-292035-07-09Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)120 °C'MSDS'
boiling point (°C)398ºC (estimate)'MSDS'
water solubilitySoluble (tartrate form)'MSDS'
logP2.15'MSDS'
Caco2 permeability-4.59ADME Research, USCD
pKa9.7Long W. Agilent Technologies. Separation of Beta Blockers at Low and High pH Using Agilent Poroshell HPH C18
Predicted Properties
PropertyValueSource
Water Solubility0.402 mg/mLALOGPS
logP1.8ALOGPS
logP1.76ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area50.72 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity76.7 m3·mol-1ChemAxon
Polarizability31.9 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9854
Blood Brain Barrier-0.8426
Caco-2 permeable+0.6895
P-glycoprotein substrateSubstrate0.7317
P-glycoprotein inhibitor INon-inhibitor0.8182
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.8418
CYP450 2C9 substrateNon-substrate0.81
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.6527
CYP450 1A2 substrateNon-inhibitor0.7018
CYP450 2C9 inhibitorNon-inhibitor0.8691
CYP450 2D6 inhibitorNon-inhibitor0.7909
CYP450 2C19 inhibitorNon-inhibitor0.9555
CYP450 3A4 inhibitorNon-inhibitor0.9476
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9897
Ames testNon AMES toxic0.9163
CarcinogenicityNon-carcinogens0.9387
BiodegradationNot ready biodegradable0.8544
Rat acute toxicity1.9180 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8368
hERG inhibition (predictor II)Non-inhibitor0.8202
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-0v0c-3248359000-0353ef81c3bc6d7fcfd5
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-014l-2514911000-b5f7785723f1eaf61e6f
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-05ir-1729351100-fb362124379cb4616c5e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01b9-9760000000-90ea4861dda115391e26
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014l-0920000000-b7c75fc96ea4b12a1f40
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0090000000-5e678ec3b5c3302abb3c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0190000000-0ea5b7fc1dda907b176b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-01b9-4940000000-5e4d95fb248589c9af91
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05gi-4900000000-73204756032f7604c22e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05fr-4900000000-597c5d64a09cf1b8f88d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zml-5900000000-ca840796f27bfcb3bd0f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0090000000-9ae9e49826b05fa823f5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0190000000-cfdea758641b8b5c956e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-01b9-3940000000-248e03350c5dfe8e1302
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05gi-4900000000-24d3886dc7605253aeb8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05gi-4900000000-08c6d3455af24f523db2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zmi-5900000000-9b22afca158afbaeb6d1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014l-0920000000-851dcbef33e79ed22643
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0090000000-61bef9702ed80c36d107
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00xr-9830000000-19e036f6e7d1698645ad
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ab9-9500000000-a0c8de4980f1bd246201
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00yi-2900000000-bcd2d1e9320ab40c0cbe
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0kn9-3900000000-a4ead9cd3340096bb484
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0970000000-af48fd7b0dbd70f65107
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014l-0920000000-91f6498b9bb55aeeacd9
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as tyrosols and derivatives. These are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
Tyrosols and derivatives
Direct Parent
Tyrosols and derivatives
Alternative Parents
Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Dialkyl ethers / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Tyrosol derivative / Phenoxy compound / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / 1,2-aminoalcohol / Secondary alcohol / Dialkyl ether / Secondary amine / Secondary aliphatic amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aromatic ether, secondary alcohol, secondary amino compound, propanolamine (CHEBI:6904)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Schafer M, Frischkopf K, Taimor G, Piper HM, Schluter KD: Hypertrophic effect of selective beta(1)-adrenoceptor stimulation on ventricular cardiomyocytes from adult rat. Am J Physiol Cell Physiol. 2000 Aug;279(2):C495-503. [PubMed:10913016]
  2. Staudt A, Mobini R, Fu M, Grosse Y, Stangl V, Stangl K, Thiele A, Baumann G, Felix SB: beta(1)-Adrenoceptor antibodies induce positive inotropic response in isolated cardiomyocytes. Eur J Pharmacol. 2001 Jul 6;423(2-3):115-9. [PubMed:11448474]
  3. Staudt Y, Mobini R, Fu M, Felix SB, Kuhn JP, Staudt A: Beta1-adrenoceptor antibodies induce apoptosis in adult isolated cardiomyocytes. Eur J Pharmacol. 2003 Apr 11;466(1-2):1-6. [PubMed:12679135]
  4. Johnson JA, Zineh I, Puckett BJ, McGorray SP, Yarandi HN, Pauly DF: Beta 1-adrenergic receptor polymorphisms and antihypertensive response to metoprolol. Clin Pharmacol Ther. 2003 Jul;74(1):44-52. [PubMed:12844134]
  5. Liu J, Liu ZQ, Tan ZR, Chen XP, Wang LS, Zhou G, Zhou HH: Gly389Arg polymorphism of beta1-adrenergic receptor is associated with the cardiovascular response to metoprolol. Clin Pharmacol Ther. 2003 Oct;74(4):372-9. [PubMed:14534524]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Zebrack JS, Munger M, Macgregor J, Lombardi WL, Stoddard GP, Gilbert EM: Beta-receptor selectivity of carvedilol and metoprolol succinate in patients with heart failure (SELECT trial): a randomized dose-ranging trial. Pharmacotherapy. 2009 Aug;29(8):883-90. doi: 10.1592/phco.29.8.883. [PubMed:19637941]

Enzymes

Details
1. Cytochrome P450 2D6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Belpaire FM, Wijnant P, Temmerman A, Rasmussen BB, Brosen K: The oxidative metabolism of metoprolol in human liver microsomes: inhibition by the selective serotonin reuptake inhibitors. Eur J Clin Pharmacol. 1998 May;54(3):261-4. [PubMed:9681670]
  2. McGinnity DF, Parker AJ, Soars M, Riley RJ: Automated definition of the enzymology of drug oxidation by the major human drug metabolizing cytochrome P450s. Drug Metab Dispos. 2000 Nov;28(11):1327-34. [PubMed:11038161]
  3. Bahar MA, Kamp J, Borgsteede SD, Hak E, Wilffert B: 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. doi: 10.1111/bcp.13741. Epub 2018 Sep 24. [PubMed:30248178]
  4. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Researchgate publications [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Morris J, Dunham A: Metoprolol . [PubMed:30422518]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Dudley AJ, Bleasby K, Brown CD: The organic cation transporter OCT2 mediates the uptake of beta-adrenoceptor antagonists across the apical membrane of renal LLC-PK(1) cell monolayers. Br J Pharmacol. 2000 Sep;131(1):71-9. [PubMed:10960071]
Details
2. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Takara K, Kakumoto M, Tanigawara Y, Funakoshi J, Sakaeda T, Okumura K: Interaction of digoxin with antihypertensive drugs via MDR1. Life Sci. 2002 Feb 15;70(13):1491-500. [PubMed:11895100]
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Drug created on June 13, 2005 07:24 / Updated on September 21, 2019 03:44