Details
Stereochemistry | RACEMIC |
Molecular Formula | 2C15H25NO3.C4H6O4 |
Molecular Weight | 652.8158 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCC(O)=O.COCCC1=CC=C(OCC(O)CNC(C)C)C=C1.COCCC2=CC=C(OCC(O)CNC(C)C)C=C2
InChI
InChIKey=RGHAZVBIOOEVQX-UHFFFAOYSA-N
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)
Mrtoprolol is a beta-adrenergic receptor blocking agent. In vitro and in vivo animal studies have shown that it has a preferential effect
on beta-1 adrenoreceptors, chiefly located in cardiac muscle. Clinical pharmacology studies have confirmed the beta-blocking activity of metoprolol in man, as shown by (1) reduction in heart rate and cardiac output at rest and upon exercise, (2) reduction of systolic blood pressure upon exercise, (3) inhibition of isoproterenol-induced tachycardia, and (4) reduction of reflex orthostatic tachycardia. Mrtoprolol is indicated for the treatment of hypertension, angina pectoris and myocardial infarction
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL213 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | LOPRESSOR Approved UseHypertension Metoprolol tartrate tablets are indicated for the treatment of hypertension. They may be used alone or in combination with other antihypertensive agents. Angina Pectoris Metoprolol tartrate tablets are indicated in the long-term treatment of angina pectoris. Myocardial Infarction Metoprolol tartrate injection and tablets are indicated in the treatment of hemodynamically stable patients with definite or suspected acute myocardial infarction to reduce cardiovascular mortality. Treatment with intravenous metoprolol tartrate can be initiated as soon as the patient’s clinical condition allows (see DOSAGE AND ADMINISTRATION , CONTRAINDICATIONS , and WARNINGS ). Alternatively, treatment can begin within 3 to 10 days of the acute event (see DOSAGE AND ADMINISTRATION ). Launch Date1978 |
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Primary | LOPRESSOR Approved UseHypertension Metoprolol tartrate tablets are indicated for the treatment of hypertension. They may be used alone or in combination with other antihypertensive agents. Angina Pectoris Metoprolol tartrate tablets are indicated in the long-term treatment of angina pectoris. Myocardial Infarction Metoprolol tartrate injection and tablets are indicated in the treatment of hemodynamically stable patients with definite or suspected acute myocardial infarction to reduce cardiovascular mortality. Treatment with intravenous metoprolol tartrate can be initiated as soon as the patient’s clinical condition allows (see DOSAGE AND ADMINISTRATION , CONTRAINDICATIONS , and WARNINGS ). Alternatively, treatment can begin within 3 to 10 days of the acute event (see DOSAGE AND ADMINISTRATION ). Launch Date1978 |
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Primary | LOPRESSOR Approved UseHypertension Metoprolol tartrate tablets are indicated for the treatment of hypertension. They may be used alone or in combination with other antihypertensive agents. Angina Pectoris Metoprolol tartrate tablets are indicated in the long-term treatment of angina pectoris. Myocardial Infarction Metoprolol tartrate injection and tablets are indicated in the treatment of hemodynamically stable patients with definite or suspected acute myocardial infarction to reduce cardiovascular mortality. Treatment with intravenous metoprolol tartrate can be initiated as soon as the patient’s clinical condition allows (see DOSAGE AND ADMINISTRATION , CONTRAINDICATIONS , and WARNINGS ). Alternatively, treatment can begin within 3 to 10 days of the acute event (see DOSAGE AND ADMINISTRATION ). Launch Date1978 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
76 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10741632/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
METOPROLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
279 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10741632/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
METOPROLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10741632/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
METOPROLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
9 h |
unknown |
METOPROLOL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
90% |
unknown |
METOPROLOL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
5000 mg single, oral Overdose |
unknown, 39 years n = 1 Health Status: unknown Condition: suicide attempt Age Group: 39 years Sex: F Population Size: 1 Sources: |
Disc. AE: Bradycardia... AEs leading to discontinuation/dose reduction: Bradycardia (1 patient) Sources: |
7500 mg single, oral Overdose |
unknown, adult n = 1 Health Status: unknown Age Group: adult Sex: unknown Population Size: 1 Sources: |
Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Bradycardia | 1 patient Disc. AE |
5000 mg single, oral Overdose |
unknown, 39 years n = 1 Health Status: unknown Condition: suicide attempt Age Group: 39 years Sex: F Population Size: 1 Sources: |
Death | grade 5, 1 patient Disc. AE |
7500 mg single, oral Overdose |
unknown, adult n = 1 Health Status: unknown Age Group: adult Sex: unknown Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/27006091/ Page: 16.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/9143866/ Page: 4.0 |
yes [Ki 570 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | yes (co-administration study) Comment: coadministration of quinidine 100 mg and immediate release metoprolol 200 mg tripled the concentration of S-metoprolol and doubled the metoprolol elimination half-life; Coadministration of metoprolol with gefitinib resulted in a 35% increase in the metoprolol area under plasma concentration-time curve from time zero to the time of the last quantifiable concentration; paroxetine increased the AUC of metoprolol three to five times, and significantly decreased systolic blood pressure and heart rate of patients; Page: 3.0 |
|||
minor | ||||
minor | ||||
minor |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Safety, hemodynamic profile, and feasibility of dobutamine stress technetium myocardial perfusion single-photon emission CT imaging for evaluation of coronary artery disease in the elderly. | 2000 Mar |
|
Effect of intravenous metoprolol or intravenous metoprolol plus glucagon on dobutamine-induced myocardial ischemia. | 2000 Nov |
|
Regression of left ventricular mass with captopril and metoprolol, and the effects on glucose and lipid metabolism. | 2001 |
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Comparative effects of three beta blockers (atenolol, metoprolol, and propranolol) on survival after acute myocardial infarction. | 2001 Apr 1 |
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Origins of heart rate variability: autonomic blockade of large magnitude, transient bradycardia in conscious rabbits. | 2001 Feb |
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Effect of beta-blockers on circulating levels of inflammatory and anti-inflammatory cytokines in patients with dilated cardiomyopathy. | 2001 Feb |
|
Sevelamer hydrochloride (Renagel), a phosphate-binding polymer, does not alter the pharmacokinetics of two commonly used antihypertensives in healthy volunteers. | 2001 Feb |
|
Hyperthyroid dementia: clinicoradiological findings and response to treatment. | 2001 Feb 15 |
|
Silent ischemic interval on exercise test is a predictor of response to drug therapy: a randomized crossover trial of metoprolol versus diltiazem in stable angina. | 2001 Jan |
|
Autonomic dysfunction in patients with mild heart failure and coronary artery disease and the effects of add-on beta-blockade. | 2001 Jan |
|
Prognostic implications of intima-media thickness and plaques in the carotid and femoral arteries in patients with stable angina pectoris. | 2001 Jan |
|
Evaluation of a vincristine resistant Caco-2 cell line for use in a calcein AM extrusion screening assay for P-glycoprotein interaction. | 2001 Jan |
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[Rhabdomyolysis as a rare complication of theophylline poisoning]. | 2001 Jan 15 |
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Enantiomeric separation of metoprolol and alpha-hydroxymetoprolol by liquid chromatography and fluorescence detection using a chiral stationary phase. | 2001 Jul 15 |
|
Differing beta-blocking effects of carvedilol and metoprolol. | 2001 Jun |
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Behavioral-independent features of complex heartbeat dynamics. | 2001 Jun 25 |
|
Anti beta1-adrenoceptor autoantibodies analyzed in spontaneously beating neonatal rat heart myocyte cultures-comparison of methods. | 2001 Mar |
|
Does acute-phase beta blockade reduce left atrial appendage function in patients with chronic nonvalvular atrial fibrillation? | 2001 Mar |
|
Effect of metoprolol on cytokine levels in chronic heart failure--a substudy in the Metoprolol Controlled-Release Randomised Intervention Trial in Heart Failure (MERIT-HF). | 2001 Mar |
|
Metoprolol CR/XL in the treatment of chronic heart failure. | 2001 May |
|
Angerlike behavioral state potentiates myocardial ischemia-induced T-wave alternans in canines. | 2001 May |
|
Stereospecific pharmacokinetics and pharmacodynamics of beta-adrenergic blockers in humans. | 2001 May-Aug |
Sample Use Guides
Hypertension
The dosage of Lopressor should be individualized. Lopressor should be taken with or immediately following meals.
The usual initial dosage is 100 mg daily in single or divided doses, whether used alone or added to a diuretic. The dosage may be
increased at weekly (or longer) intervals until optimum blood pressure reduction is achieved. In general, the maximum effect of
any given dosage level will be apparent after 1 week of therapy. The effective dosage range is 100-450 mg per day. Dosages above
450 mg per day have not been studied. While once-daily dosing is effective and can maintain a reduction in blood pressure throughout
the day, lower doses (especially 100 mg) may not maintain a full effect at the end of the 24-hour period, and larger or more frequent
daily doses may be required. This can be evaluated by measuring blood pressure near the end of the dosing interval to determine
whether satisfactory control is being maintained throughout the day. Beta1 selectivity diminishes as the dose of Lopressor is increased.
Angina Pectoris
The dosage of Lopressor should be individualized. Lopressor should be taken with or immediately following meals.
The usual initial dosage is 100 mg daily, given in two divided doses. The dosage may be gradually increased at weekly intervals
until optimum clinical response has been obtained or there is pronounced slowing of the heart rate. The effective dosage range is
100-400 mg per day. Dosages above 400 mg per day have not been studied. If treatment is to be discontinued, the dosage should be
reduced gradually over a period of 1-2 weeks (see WARNINGS).
Myocardial Infarction
Early Treatment: During the early phase of definite or suspected acute myocardial infarction, treatment with Lopressor can be
initiated as soon as possible after the patient’s arrival in the hospital. Such treatment should be initiated in a coronary care or similar
unit immediately after the patient’s hemodynamic condition has stabilized.
Treatment in this early phase should begin with the intravenous administration of three bolus injections of 5 mg of Lopressor each; the
injections should be given at approximately 2-minute intervals. During the intravenous administration of Lopressor, blood pressure,
heart rate, and electrocardiogram should be carefully monitored.
In patients who tolerate the full intravenous dose (15 mg), Lopressor tablets, 50 mg every 6 hours, should be initiated 15 minutes after
the last intravenous dose and continued for 48 hours. Thereafter, patients should receive a maintenance dosage of 100 mg twice daily
(see Late Treatment below).
Patients who appear not to tolerate the full intravenous dose should be started on Lopressor tablets either 25 mg or 50 mg every
6 hours (depending on the degree of intolerance) 15 minutes after the last intravenous dose or as soon as their clinical condition
allows. In patients with severe intolerance, treatment with Lopressor should be discontinued (see WARNINGS).
Late Treatment: Patients with contraindications to treatment during the early phase of suspected or definite myocardial infarction,
patients who appear not to tolerate the full early treatment, and patients in whom the physician wishes to delay therapy for any other
reason should be started on Lopressor tablets, 100 mg twice daily, as soon as their clinical condition allows. Therapy should be
continued for at least 3 months. Although the efficacy of Lopressor beyond 3 months has not been conclusively established, data from
studies with other beta blockers suggest that treatment should be continued for 1-3 years.
Note: Parenteral drug products should be inspected visually for particulate matter and discoloration prior to administration,
whenever solution and container permit.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27300117
0.01 to 0.1 uM metoprolol increased osteoblast proliferation, alkaline phosphatase activity, and calcium mineralization, and promoted the expression of osteogenic genes.
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NCI_THESAURUS |
C29576
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100000091368
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CHEMBL13
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123245-49-8
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C402833
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C29254
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m7498
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DD-24
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ACTIVE MOIETY
SUBSTANCE RECORD