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

Details

Stereochemistry RACEMIC
Molecular Formula C15H25NO3
Molecular Weight 267.3645
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METOPROLOL

SMILES

CC(C)NCC(COc1ccc(cc1)CCOC)O

InChI

InChIKey=IUBSYMUCCVWXPE-UHFFFAOYSA-N
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

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

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
Cost-effectiveness of antihypertensive treatment: metoprolol versus thiazide diuretics.
1993 Jan
Potent and selective human beta(3)-adrenergic receptor antagonists.
1999 Aug
LK 204-545, a highly selective beta1-adrenoceptor antagonist at human beta-adrenoceptors.
1999 Feb 19
Effects of beta-receptor blockade and angiotensin II type I receptor antagonism in isoproterenol-induced heart failure in the rat.
1999 Nov-Dec
MERIT-HF mortality and morbidity data.
2000
Syndrome of inappropriate antidiuretic hormone secretion associated with lisinopril.
2000 Feb
Beta-blockade in adriamycin-induced cardiomyopathy.
2000 Jun
Effect of intravenous metoprolol or intravenous metoprolol plus glucagon on dobutamine-induced myocardial ischemia.
2000 Nov
Syncope in pharmacologically unmasked Brugada syndrome: indication for an implantable defibrillator or an unresolved dilemma?
2001 Apr
Giant R-waves in a patient with an acute inferior myocardial infarction.
2001 Apr
Characterization of beta(1)-selectivity, adrenoceptor-G(s)-protein interaction and inverse agonism of nebivolol in human myocardium.
2001 Apr
Low-dose metoprolol CR/XL and fluvastatin slow progression of carotid intima-media thickness: Main results from the Beta-Blocker Cholesterol-Lowering Asymptomatic Plaque Study (BCAPS).
2001 Apr 3
Quantitative structure-retention and retention-activity relationships of beta-blocking agents by micellar liquid chromatography.
2001 Apr 6
Anti-ischaemic efficacy and tolerability of trimetazidine administered to patients with angina pectoris: results of three studies.
2001 Feb
On glomerular structural alterations in type-1 diabetes. Companions of early diabetic glomerulopathy.
2001 Feb
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
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
Effects of nebivolol on proliferation and apoptosis of human coronary artery smooth muscle and endothelial cells.
2001 Feb 1
Selective beta(1)-blockade improves cardiac bioenergetics and function and decreases neuroendocrine activation in rats during early postinfarct remodeling.
2001 Feb 23
Acute renal ischemia model in dogs: effects of metoprolol.
2001 Jan
Evidence for the binding of beta-adrenoceptor blockers to microsomal Na+/K+-ATPase in guinea pig heart preparations.
2001 Jan
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
Medical and revascularization management in acute coronary syndrome in renal patients.
2001 Jan
Oxygen consumption in patients with hyperthyroidism before and after treatment with beta-blockade versus thyrostatic treatment: a prospective randomized study.
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
Catecholamines stimulate interleukin-6 synthesis in rat cardiac fibroblasts.
2001 Jul
Enantiomeric separation of metoprolol and alpha-hydroxymetoprolol by liquid chromatography and fluorescence detection using a chiral stationary phase.
2001 Jul 15
beta(1)-Adrenoceptor antibodies induce positive inotropic response in isolated cardiomyocytes.
2001 Jul 6
Cardioprotective effect of propranolol from alcohol-induced heart muscle damage as assessed by plasma cardiac troponin-t.
2001 Jun
Beta-blockade in chronic heart failure.
2001 Jun 12
Nebivolol, carvedilol and metoprolol do not influence cardiac Ca(2+) sensitivity.
2001 Jun 22
Metoprolol attenuates postischemic depressed myocardial function in papillary muscles isolated from normal and postinfarction rat hearts.
2001 Jun 22
[Adrenergic beta inhibitors in heart insufficiency: which and when?].
2001 Mar
Effect of beta blockers on mortality and morbidity in persons treated for congestive heart failure.
2001 Mar
Does acute-phase beta blockade reduce left atrial appendage function in patients with chronic nonvalvular atrial fibrillation?
2001 Mar
Extracellular matrix proteins in cardiac fibroblasts derived from rat hearts with chronic pressure overload: effects of beta-receptor blockade.
2001 Mar
Are all beta-blockers the same for chronic heart failure?
2001 Mar
Benefits of beta-blockers in heart failure: a class specific effect?
2001 May
Overview of the results of recent beta blocker trials.
2001 May
Metoprolol-paroxetine interaction in human liver microsomes: stereoselective aspects and prediction of the in vivo interaction.
2001 May
Stereospecific pharmacokinetics and pharmacodynamics of beta-adrenergic blockers in humans.
2001 May-Aug
Calcineurin-GATA4 pathway is involved in beta-adrenergic agonist-responsive endothelin-1 transcription in cardiac myocytes.
2001 Sep 14
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
HSDB   INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
METOPROLOL [INN]
Common Name English
(RS)-METOPROLOL
Common Name English
METOPROLOL [HSDB]
Common Name English
METOPROLOL SLOW RELEASE
Common Name English
BEATROLOL
Brand Name English
METOPROLOL [WHO-DD]
Common Name English
CGP-2175
Code English
METOPROLOL [VANDF]
Common Name English
2-PROPANOL, 1-(4-(2-METHOXYETHYL)PHENOXY)-3-((1-METHYLETHYL)AMINO)-
Systematic Name English
SEROKEN
Brand Name English
METOPROLOL [MART.]
Common Name English
1-(4-(2-METHOXYETHYL)PHENOXY)-3-((1-METHYLETHYL)AMINO)-2-PROPANOL
Systematic Name English
1-(ISOPROPYLAMINO)-3-(4-(2-METHOXYETHYL)PHENOXY)PROPAN-2-OL
Systematic Name English
DL-METOPROLOL
Common Name English
METOPROLOL [USAN]
Common Name English
H-93/26
Code English
METOPROLOL, (+/-)-
Common Name English
METOPROLOL [MI]
Common Name English
(+/-)-METOPROLOL
Common Name English
Classification Tree Code System Code
WHO-ATC C07FX03
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-ATC C07BB52
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
LIVERTOX 631
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-ATC C07BB02
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-ATC C07AB02
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-VATC QC07BB02
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-ATC C07FB02
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-ATC C07CB02
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-VATC QC07AB02
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-ATC C07FX05
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-VATC QC07AB52
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
NDF-RT N0000175556
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-VATC QC07CB02
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-VATC QC07FB02
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
NDF-RT N0000000161
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-ATC C07AB52
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
NCI_THESAURUS C29576
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
FDA ORPHAN DRUG 804320
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-VATC QC07BB52
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
WHO-ATC C07FB13
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
253-483-7
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
ALTERNATIVE
CAS
51384-51-1
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
WIKIPEDIA
METOPROLOL
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
ECHA (EC/EINECS)
257-166-4
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
EPA CompTox
51384-51-1
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
CAS
37350-58-6
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
SUPERSEDED
MESH
D008790
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
LACTMED
Metoprolol
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL13
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
FDA UNII
GEB06NHM23
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
RXCUI
6918
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00264
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
HSDB
6531
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
IUPHAR
553
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
EVMPD
SUB14568MIG
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
MERCK INDEX
M7498
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
1786
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
NCI_THESAURUS
C61845
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
INN
3471
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY
CAS
54163-88-1
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
SUPERSEDED
PUBCHEM
4171
Created by admin on Fri Jun 25 21:30:45 UTC 2021 , Edited by admin on Fri Jun 25 21:30:45 UTC 2021
PRIMARY