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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
Structure of METOPROLOL SUCCINATE

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)

HIDE SMILES / InChI
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

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LOPRESSOR

Approved Use

Hypertension 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 Date

1978
Primary
LOPRESSOR

Approved Use

Hypertension 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 Date

1978
Primary
LOPRESSOR

Approved Use

Hypertension 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 Date

1978
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
76 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
279 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2.8 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
90%
unknown
METOPROLOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5000 mg single, oral
Overdose
Dose: 5000 mg
Route: oral
Route: single
Dose: 5000 mg
Sources:
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
Dose: 7500 mg
Route: oral
Route: single
Dose: 7500 mg
Sources:
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

AEs

AESignificanceDosePopulation
Bradycardia 1 patient
Disc. AE
5000 mg single, oral
Overdose
Dose: 5000 mg
Route: oral
Route: single
Dose: 5000 mg
Sources:
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
Dose: 7500 mg
Route: oral
Route: single
Dose: 7500 mg
Sources:
unknown, adult
n = 1
Health Status: unknown
Age Group: adult
Sex: unknown
Population Size: 1
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
yes [Ki 570 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical 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

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
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
Comparative effects of three beta blockers (atenolol, metoprolol, and propranolol) on survival after acute myocardial infarction.
2001 Apr 1
Origins of heart rate variability: autonomic blockade of large magnitude, transient bradycardia in conscious rabbits.
2001 Feb
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
[Rhabdomyolysis as a rare complication of theophylline poisoning].
2001 Jan 15
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
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
Patents

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
0.01 to 0.1 uM metoprolol increased osteoblast proliferation, alkaline phosphatase activity, and calcium mineralization, and promoted the expression of osteogenic genes.
Name Type Language
METOPROLOL SUCCINATE
EP   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
2-PROPANOL, 1-(4-(2-METHOXYETHYL)PHENOXY)-3-((1-METHYLETHYL)AMINO)-, (±)-, BUTANEDIOATE (2:1) (SALT)
Common Name English
METOPROLOL SUCCINATE [USP-RS]
Common Name English
METOPROLOL SUCCINATE [VANDF]
Common Name English
TOPROL-XL
Brand Name English
METOPROLOL SUCCINATE [MART.]
Common Name English
H 93/26 SUCCINATE
Code English
(±)-1-(ISOPROPYLAMINO)-3-(P-(2-METHOXYETHYL)PHENOXY)-2-PROPANOL SUCCINATE (2:1) (SALT)
Common Name English
TOPROL
Brand Name English
METOPROLOL SUCCINATE [EP IMPURITY]
Common Name English
SELOZOK
Brand Name English
METOPROLOL SUCCINATE [USP MONOGRAPH]
Common Name English
Metoprolol succinate [WHO-DD]
Common Name English
METOPROLOL SUCCINATE [EP MONOGRAPH]
Common Name English
DUTOPROL COMPONENT METOPROLOL SUCCINATE
Common Name English
SELOKEN-ZOK
Brand Name English
METOPROLOL SUCCINATE COMPONENT OF DUTOPROL
Common Name English
METOPROLOL SUCCINATE [USAN]
Common Name English
METOPROLOL SUCCINATE [MI]
Common Name English
METOPROLOL HEMISUCCINATE
Common Name English
METOPROLOL SUCCINATE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 15:51:12 GMT 2023 , Edited by admin on Fri Dec 15 15:51:12 GMT 2023
Code System Code Type Description
FDA UNII
TH25PD4CCB
Created by admin on Fri Dec 15 15:51:12 GMT 2023 , Edited by admin on Fri Dec 15 15:51:12 GMT 2023
PRIMARY
SMS_ID
100000091368
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PRIMARY
RS_ITEM_NUM
1441298
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PRIMARY
CAS
98418-47-4
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PRIMARY
ChEMBL
CHEMBL13
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PRIMARY
CAS
123245-49-8
Created by admin on Fri Dec 15 15:51:12 GMT 2023 , Edited by admin on Fri Dec 15 15:51:12 GMT 2023
NON-SPECIFIC STOICHIOMETRY
EPA CompTox
DTXSID9048726
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PRIMARY
DAILYMED
TH25PD4CCB
Created by admin on Fri Dec 15 15:51:12 GMT 2023 , Edited by admin on Fri Dec 15 15:51:12 GMT 2023
PRIMARY
MESH
C402833
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PRIMARY
EVMPD
SUB03274MIG
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PRIMARY
RXCUI
221124
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PRIMARY RxNorm
NCI_THESAURUS
C29254
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PRIMARY
MERCK INDEX
m7498
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PRIMARY Merck Index
PUBCHEM
62937
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PRIMARY
USAN
DD-24
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PRIMARY
DRUG BANK
DBSALT000863
Created by admin on Fri Dec 15 15:51:12 GMT 2023 , Edited by admin on Fri Dec 15 15:51:12 GMT 2023
PRIMARY