U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry EPIMERIC
Molecular Formula 2C15H25NO3.C4H6O6
Molecular Weight 684.8146
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METOPROLOL TARTRATE

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.COCCC1=CC=C(OCC(O)CNC(C)C)C=C1.COCCC2=CC=C(OCC(O)CNC(C)C)C=C2

InChI

InChIKey=YGULWPYYGQCFMP-CEAXSRTFSA-N
InChI=1S/2C15H25NO3.C4H6O6/c2*1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3;5-1(3(7)8)2(6)4(9)10/h2*4-7,12,14,16-17H,8-11H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t;;1-,2-/m..1/s1

HIDE SMILES / InChI

Molecular Formula C15H25NO3
Molecular Weight 267.3639
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

2.71296004E11
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

2.71296004E11
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

2.71296004E11
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
Early alterations of polyamine metabolism induced after acute administration of clenbuterol in mouse heart.
1999
MERIT-HF mortality and morbidity data.
2000
Comparative effects of three beta blockers (atenolol, metoprolol, and propranolol) on survival after acute myocardial infarction.
2001 Apr 1
Effect of metoprolol on rest and exercise left ventricular systolic and diastolic function in idiopathic dilated cardiomyopathy.
2001 Feb
Asymptomatic atrial fibrillation: problems of management.
2001 Feb
Selective beta(1)-blockade improves cardiac bioenergetics and function and decreases neuroendocrine activation in rats during early postinfarct remodeling.
2001 Feb 23
Sotalol vs metoprolol for ventricular rate control in patients with chronic atrial fibrillation who have undergone digitalization: a single-blinded crossover study.
2001 Jan
Acute renal ischemia model in dogs: effects of metoprolol.
2001 Jan
Medical and revascularization management in acute coronary syndrome in renal patients.
2001 Jan
Autonomic dysfunction in patients with mild heart failure and coronary artery disease and the effects of add-on beta-blockade.
2001 Jan
Antioxidant properties of carvedilol and metoprolol in heart failure: a double-blind randomized controlled trial.
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
Influence of beta-adrenoceptor antagonists on the pharmacokinetics of rizatriptan, a 5-HT1B/1D agonist: differential effects of propranolol, nadolol and metoprolol.
2001 Jul
Statistical issues relating to international differences in clinical trials.
2001 Jul
Enantiomeric separation of metoprolol and alpha-hydroxymetoprolol by liquid chromatography and fluorescence detection using a chiral stationary phase.
2001 Jul 15
Effect of lipophilicity on in vivo iontophoretic delivery. II. Beta-blockers.
2001 Jun
Effect of ramipril vs amlodipine on renal outcomes in hypertensive nephrosclerosis: a randomized controlled trial.
2001 Jun 6
[Adrenergic beta inhibitors in heart insufficiency: which and when?].
2001 Mar
Anti beta1-adrenoceptor autoantibodies analyzed in spontaneously beating neonatal rat heart myocyte cultures-comparison of methods.
2001 Mar
Extracellular matrix proteins in cardiac fibroblasts derived from rat hearts with chronic pressure overload: effects of beta-receptor blockade.
2001 Mar
Overview of the results of recent beta blocker trials.
2001 May
Metoprolol CR/XL in the treatment of chronic heart failure.
2001 May
Carvedilol in the treatment of chronic heart failure.
2001 May
Metoprolol-paroxetine interaction in human liver microsomes: stereoselective aspects and prediction of the in vivo interaction.
2001 May
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:20:47 UTC 2023
Edited
by admin
on Fri Dec 15 15:20:47 UTC 2023
Record UNII
W5S57Y3A5L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METOPROLOL TARTRATE
EP   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
SELOKEN
Brand Name English
METOPROLOL TARTRATE [USP MONOGRAPH]
Common Name English
METOPROLOL TARTRATE [ORANGE BOOK]
Common Name English
METOPROLOL TARTRATE [USAN]
Common Name English
METOPROLOL TARTRATE [USP-RS]
Common Name English
LOPRESOR
Brand Name English
LOPRESSIDONE COMPONENT METOPROLOL TARTRATE
Common Name English
METOPROLOL TARTRATE [MI]
Common Name English
METROPRESS
Brand Name English
PRELIS
Brand Name English
BELOC
Brand Name English
CGP-2175E
Code English
METOPROLOL HEMITARTRATE
Common Name English
METOPROLOL TARTRATE [EP MONOGRAPH]
Common Name English
METOPROLOL TARTRATE [VANDF]
Common Name English
Metoprolol tartrate [WHO-DD]
Common Name English
(±)-1-(ISOPROPYLAMINO)-3-(P-(2-METHOXYETHYL)PHENOXY)-2-PROPANOL L-(+)-TARTRATE (2:1) (SALT)
Common Name English
METOPROLOL TARTRATE [JAN]
Common Name English
2-PROPANOL, 1-(4-(2-METHOXYETHYL)PHENOXY)-3-((1-METHYLETHYL)AMINO)-, (±)-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (2:1) (SALT)
Common Name English
LOPRESSOR HCT COMPONENT METOPROLOL TARTRATE
Common Name English
LOPRESSOR
Brand Name English
1-ISOPROPYLAMINO-3-(P-(2-METHOXYETHYL)PHENOXY)-2-PROPANOL (2:1) DEXTRO-TARTRATE SALT
Common Name English
BETALOC
Brand Name English
METOPROLOL TARTRATE COMPONENT OF LOPRESSIDONE
Common Name English
METOPROLOL TARTRATE COMPONENT OF LOPRESSOR HCT
Common Name English
METOPROLOL TARTRATE [MART.]
Common Name English
SELOPRAL
Brand Name English
NSC-757105
Code English
Classification Tree Code System Code
CFR 21 CFR 331.11
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
Code System Code Type Description
PUBCHEM
441308
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
FDA UNII
W5S57Y3A5L
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
RS_ITEM_NUM
1441301
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
MERCK INDEX
m7498
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY Merck Index
EVMPD
SUB03275MIG
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
DRUG BANK
DBSALT000862
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
EPA CompTox
DTXSID9037248
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
CAS
56392-17-7
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
RXCUI
203191
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY RxNorm
DAILYMED
W5S57Y3A5L
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
ChEMBL
CHEMBL13
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
ECHA (EC/EINECS)
260-148-9
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
SMS_ID
100000090389
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
NCI_THESAURUS
C29255
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
NSC
757105
Created by admin on Fri Dec 15 15:20:47 UTC 2023 , Edited by admin on Fri Dec 15 15:20:47 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
any spot, apart from the principal spot, is not more intense than the spot in the chromatogram obtained with reference solution (a) (0.5 per cent) and at most 1 such spot is more intense than the spot in the chromatogram obtained with reference solution (b) (0.2 per cent)
CHROMATOGRAPHIC PURITY (TLC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
any spot, apart from the principal spot, is not more intense than the spot in the chromatogram obtained with reference solution (a) (0.5 per cent) and at most 1 such spot is more intense than the spot in the chromatogram obtained with reference solution (b) (0.2 per cent)
CHROMATOGRAPHIC PURITY (TLC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
ORAL BIOAVAILABILITY PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC POOR CYP2D6 METABOLIZERS
PHARMACOKINETIC
HEPATIC IMPAIRMENT
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC