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

Details

Stereochemistry RACEMIC
Molecular Formula C22H25F2NO4.ClH
Molecular Weight 441.896
Optical Activity ( + / - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEBIVOLOL HYDROCHLORIDE

SMILES

Cl.[H][C@]1(CCC2=CC(F)=CC=C2O1)[C@H](O)CNC[C@@H](O)[C@@]3([H])CCC4=C(O3)C=CC(F)=C4

InChI

InChIKey=JWEXHQAEWHKGCW-VCVZPGOSSA-N
InChI=1S/C22H25F2NO4.ClH/c23-15-3-7-19-13(9-15)1-5-21(28-19)17(26)11-25-12-18(27)22-6-2-14-10-16(24)4-8-20(14)29-22;/h3-4,7-10,17-18,21-22,25-27H,1-2,5-6,11-12H2;1H/t17-,18-,21-,22+;/m1./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H25F2NO4
Molecular Weight 405.435
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Nebivolol is a competitive and highly selective beta-1 receptor antagonist with mild vasodilating properties, possibly due to an interaction with the L-arginine/nitric oxide pathway. In preclinical studies, nebivolol has been shown to induce endothelium-dependent arterial relaxation in a dose dependent manner, by stimulation of the release of endothelial nitric oxide. Nitric oxide acts to relax vascular smooth muscle cells and inhibits platelet aggregation and adhesion. Activation of β1-receptors by epinephrine increases the heart rate and the blood pressure, and the heart consumes more oxygen. Nebivolol blocks these receptors which reverses the effects of epinephrine, lowering the heart rate and blood pressure. In addition, beta blockers prevent the release of renin, which is a hormone produced by the kidneys which leads to constriction of blood vessels. At high enough concentrations, this drug may also bind beta 2 receptors. Marketed under the brand name BYSTOLIC, Nebivolol is indicated for the treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. The beta-blocking effects of nebivolol reside in the d-isomer. Nebivolol is a racemic combination of Dexnebivolol (d-nebivolol, +SRRR nebivolol) and l-nebivolol (-RSSS nebivolol) that differs chemically from other beta-blockers, with an absolutely symmetrical configuration developing from a central nitrogen atom. D-nebivolol and l-nebivolol divaricate pharmacologically and therapeutically, with a noticeably different profile from that of conventional beta-blockers; for instance, the selective blocking of beta(1)-adrenoceptors is determined almost exclusively by d-nebivolol. Both enantiomers act synergistically with respect to blood pressure reduction: the effect of nebivolol on heart rate is exclusively exerted by d-nebivolol, with these hypotensive effects enhanced by the addition of the l-enantiomer, which in itself does not influence systolic and diastolic blood pressure. Isomer d-nebivolol (SRRR) is a β1 adrenergic receptor blocker and its antipode, l-nebivolol (RSSS) is responsible for endothelium-dependent NO liberation. d-Nebivolol (SRRR) and nebivolol showed combined high affinity and selectivity for inhibition of beta 1-adrenergic receptor coupled accumulation of cAMP in CHO-Hu beta 1 cells (0.41 and 0.42 nM for d-nebivolol and nebivolol, respectively). l-Nebivolol (RSSS) was 1460 times less potent than d-nebivolol in CHO-Hu beta 1 cells. The binding affinities of d-nebivolol and nebivolol for human beta 1-adrenergic binding sites correlated well with their potencies in inhibiting beta 1-adrenergic receptor coupled accumulation of cAMP.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BYSTOLIC

Approved Use

BYSTOLIC is a beta-adrenergic blocking agent indicated for the treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. BYSTOLIC may be used alone or in combination with other antihypertensive agents .

Launch Date

1.19784958E12
Primary
BYSTOLIC

Approved Use

BYSTOLIC is a beta-adrenergic blocking agent indicated for the treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. BYSTOLIC may be used alone or in combination with other antihypertensive agents .

Launch Date

1.1977632E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.48 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEBIVOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
7.76 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEBIVOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEBIVOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
unknown
NEBIVOLOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
acetylsalicylic acid, oral(>100 mg)
Sources: Page: p.8
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.8
Disc. AE: Hyperhidrosis, Pallor...
AEs leading to
discontinuation/dose reduction:
Hyperhidrosis
Pallor
Depressed level of consciousness
Hypokinesia
Hypotension
Sinus bradycardia
Hypoglycemia
Hypokalemia
Respiratory failure
Vomiting
Sources: Page: p.8
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.4
unhealthy
n = 6545
Health Status: unhealthy
Condition: Hypertension
Population Size: 6545
Sources: Page: p.4
Disc. AE: Headache, Nausea...
AEs leading to
discontinuation/dose reduction:
Headache (0.4%)
Nausea (0.2%)
Bradycardia (0.2%)
Sources: Page: p.4
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Co-administed with::
valsartan, oral(80 mg, qd)
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources: Page: p.1
Disc. AE: Disorder fetal...
AEs leading to
discontinuation/dose reduction:
Disorder fetal
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Depressed level of consciousness Disc. AE
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
acetylsalicylic acid, oral(>100 mg)
Sources: Page: p.8
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.8
Hyperhidrosis Disc. AE
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
acetylsalicylic acid, oral(>100 mg)
Sources: Page: p.8
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.8
Hypoglycemia Disc. AE
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
acetylsalicylic acid, oral(>100 mg)
Sources: Page: p.8
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.8
Hypokalemia Disc. AE
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
acetylsalicylic acid, oral(>100 mg)
Sources: Page: p.8
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.8
Hypokinesia Disc. AE
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
acetylsalicylic acid, oral(>100 mg)
Sources: Page: p.8
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.8
Hypotension Disc. AE
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
acetylsalicylic acid, oral(>100 mg)
Sources: Page: p.8
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.8
Pallor Disc. AE
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
acetylsalicylic acid, oral(>100 mg)
Sources: Page: p.8
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.8
Respiratory failure Disc. AE
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
acetylsalicylic acid, oral(>100 mg)
Sources: Page: p.8
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.8
Sinus bradycardia Disc. AE
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
acetylsalicylic acid, oral(>100 mg)
Sources: Page: p.8
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.8
Vomiting Disc. AE
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
acetylsalicylic acid, oral(>100 mg)
Sources: Page: p.8
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.8
Bradycardia 0.2%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.4
unhealthy
n = 6545
Health Status: unhealthy
Condition: Hypertension
Population Size: 6545
Sources: Page: p.4
Nausea 0.2%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.4
unhealthy
n = 6545
Health Status: unhealthy
Condition: Hypertension
Population Size: 6545
Sources: Page: p.4
Headache 0.4%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.4
unhealthy
n = 6545
Health Status: unhealthy
Condition: Hypertension
Population Size: 6545
Sources: Page: p.4
Disorder fetal Disc. AE
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Co-administed with::
valsartan, oral(80 mg, qd)
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources: Page: p.1
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
minor
yes
yes (co-administration study)
Comment: from product label: fluoxetine coadministration led to increased AUC by 8% and Cmax by 3-fold
Page: 17.0
PubMed

PubMed

TitleDatePubMed
Relationship between the sympatholytic action of nebivolol and hypotension.
1992 Jul
[Effect of nebivolol on the level of constitutional, inducible, and total NO-synthase in serum of patients with type II diabetes mellitus].
2002
[Effect of enape combined with nebilet in hypertension].
2002
[Functional and biochemical characteristics of the vasodilator effects of nebivolol in patients with arterial hypertension].
2002
[Assessment of efficacy and safety of nebivolol in patients with stable effort angina].
2002
[Effects of nebivolol on microcirculation, platelet aggregation and blood viscosity in patients with essential hypertension].
2002
[Experience of the use of nebivolol in the treatment of hypertension in postmenopausal women].
2002
[Effect of nebivolol on dynamics of microalbuminuria, renal blood flow and 24-hour blood pressure profile in patients with hypertension].
2002
[Effect of nebivolol on remodeling of the heart and vessels and the state of hemodynamics in patients with hypertension].
2002
Gateways to clinical trials.
2002 Dec
No-dependent vasodilation induced by nebivolol in coronary circulation is not mediated by beta-adrenoceptors or by 5 HT1A-receptors.
2002 Dec
[Beta blocker enhances NO liberation in the endothelium. Vascular tone long-term improvement].
2002 Dec 5
Nebivolol ameliorates nitric oxide deficient hypertension.
2002 Jun 20
[Nebivolol effects on platelet aggregation and anticoagulation system].
2003
[Heart rate control with nebivolol in patients with tachysystolic atrial fibrillation].
2003
[The use of nebivolol in menopausal women with hypertension].
2003
[Dynamics of a 24-h profile of arterial pressure and function of the vascular endothelium in nebivolol treatment of hypertensive patients].
2003
[Pharmacological modulation of NO synthesis in patients with arterial hypertension and endothelial dysfunction].
2003
[Effect of nebivolol on the state of pituitary-gonadal system and lipid peroxidation in young and middle aged men with hypertension].
2003
[Clinical and metabolic effects of cardioselective beta-adrenoblockers nebivolol and metoprolol in patients with hypertension and ischemic heart disease associated with type 2 diabetes].
2003
[Use of nebivolol in patients with mild and moderate hypertension].
2003
[Hemodynamic effects of the beta blocker nebivolol].
2003 Apr
Angiotensin-converting enzyme inhibition but not beta-adrenergic blockade limits transforming growth factor-beta overexpression in acute normotensive anti-thy1 glomerulonephritis.
2003 Apr
Nebivolol prevents vascular NOS III uncoupling in experimental hyperlipidemia and inhibits NADPH oxidase activity in inflammatory cells.
2003 Apr 1
Involvement of the beta3 adrenoceptor in nebivolol-induced vasorelaxation in the rat aorta.
2003 Aug
Comparison of effects on systolic and diastolic left ventricular function of nebivolol versus atenolol in patients with uncomplicated essential hypertension.
2003 Aug 1
Lack of inverse agonistic activity of nebivolol, its D- and L-enantiomers and of in vivo metabolized nebivolol in human myocardium.
2003 Aug 22
Efficacy and tolerability profile of nebivolol vs atenolol in mild-to-moderate essential hypertension: results of a double-blind randomized multicentre trial.
2003 Dec
[Beta blocker improves the endothelial function. Gas-forming blood vessel protection].
2003 Dec 18
Effect of forced titration of nebivolol on response rate in obese hypertensive patients.
2003 Jan
[Influence of the beta-blocker nebivolol on left ventricular function in patients with chronic heart failure].
2003 Jan 15
Beta 1-adrenoceptor selectivity of nebivolol and bisoprolol. A comparison of [3H]CGP 12.177 and [125I]iodocyanopindolol binding studies.
2003 Jan 26
The combination of nebivolol plus pravastatin is associated with a more beneficial metabolic profile compared to that of atenolol plus pravastatin in hypertensive patients with dyslipidemia: a pilot study.
2003 Jun
A comparison of the beta1-selectivity of three beta1-selective beta-blockers.
2003 Jun
Different effect of antihypertensive drugs on conduit artery endothelial function.
2003 Jun
Third-generation beta-blockers stimulate nitric oxide release from endothelial cells through ATP efflux: a novel mechanism for antihypertensive action.
2003 Jun 3
Comparison of the new cardioselective beta-blocker nebivolol with bisoprolol in hypertension: the Nebivolol, Bisoprolol Multicenter Study (NEBIS).
2003 May
Evaluation of the efficacy and tolerability of nebivolol versus lisinopril in the treatment of essential arterial hypertension: a randomized, multicentre, double-blind study.
2003 May
Effects of nebivolol on ischemia-induced metabolic changes in dog hearts.
2003 May
[Initial data on nebivolol in heart failure. Beta blockers strengthen older hearts, too].
2003 May 29
Nebivolol and its 4-keto derivative increase nitric oxide in endothelial cells by reducing its oxidative inactivation.
2003 Nov 19
Beta-blocker treatment of patients with diastolic heart failure and arterial hypertension. A prospective, randomized, comparison of the long-term effects of atenolol vs. nebivolol.
2003 Oct
[Beta-1 blockade plus NO release. Additional organ protection for patients with hypertension].
2003 Oct 2
Long-term treatment with nebivolol improves arterial reactivity and reduces ventricular hypertrophy in spontaneously hypertensive rats.
2003 Sep
[Endothelial dysfunction and metabolic effects of nitric oxide in human].
2003 Sep-Oct
[Nebivolol in the treatment of ischemic heart disease patients with chronic heart failure].
2004
The shift in the "paradigm" of the pharmacology of hypertension.
2004
[Genetic polymorphisms in drug metabolizing enzymes--impact on treatment with beta-blockers].
2004 Apr 8
Antioxidant activity of nebivolol in the rat aorta.
2004 Jan
Comparative effects of a two-week treatment with nebivolol and nifedipine in hypertensive patients suffering from COPD.
2004 Mar-Apr
Patents

Sample Use Guides

Can be taken with and without food. Individualize to the needs of the patient and monitor during up-titration. (2) • Hypertension: Most patients start at 5 mg once daily. Dose can be increased at 2-week intervals up to 40 mg.
Route of Administration: Oral
Nebivolol reduces cell proliferation of human coronary smooth muscle cells (haCSMCs) and endothelial cells (haECs) in a concentration- and time-dependent maner. Nebivolol treatment for 7 days causes significant reduction in cell growth of haCSMCs with IC50 of 6.1 uM, and inhibits accelerated haCSMC proliferation stimulated by growth factors PDGF-BB, bFGF, and TGFβ with IC50 values of 6.8 uM, 6.4 uM and 7.7 uM, repectively. Nebivolol treatment (10-5 M) of haCSMCs for 48 hours induces a moderate apoptosis of 23% and a decrease from 16% to 5% in the number of cells in S-phase. During Nebivolol incubation, NO formation of HaCEs increases, while endothelin-1 transcription and secretion are suppressed.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:20:37 UTC 2023
Edited
by admin
on Wed Jul 05 23:20:37 UTC 2023
Record UNII
JGS34J7L9I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEBIVOLOL HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
BYSTOLIC
Brand Name English
BYVALSON COMPONENT NEBIVOLOL HYDROCHLORIDE
Brand Name English
NEBIVOLOL HYDROCHLORIDE [USP-RS]
Common Name English
(1RS,1'RS)-1,1'-((2RS,2'SR)-BIS(6-FLUORO-3,4-DIHYDRO-2H-1-BENZOPYRAN-2-YL))-2,2'-IMINODIETHANOL HYDROCHLORIDE
Common Name English
NEBIVOLOL HYDROCHLORIDE [ORANGE BOOK]
Common Name English
NEBIVOLOL HYDROCHLORIDE [MART.]
Common Name English
R067555
Code English
2H-1-BENZOPYRAN-2-METHANOL, .ALPHA,.ALPHA.'-(IMINOBIS(METHYLENE))BIS(6-FLUORO-3,4-DIHYDRO-, HYDROCHLORIDE, (.ALPHA.R,.ALPHA.'R,2R,2'S)-REL-
Common Name English
Nebivolol hydrochloride [WHO-DD]
Common Name English
R-067555
Code English
NEBIVOLOL HYDROCHLORIDE [USAN]
Common Name English
NEBIVOLOL HCL
Common Name English
NEBIVOLOL HYDROCHLORIDE COMPONENT OF BYVALSON
Brand Name English
NEBIVOLOL HYDROCHLORIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
Code System Code Type Description
FDA UNII
JGS34J7L9I
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
USAN
QQ-75
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
MERCK INDEX
M7786
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C81656
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
RS_ITEM_NUM
1457833
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
SMS_ID
100000093063
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
EVMPD
SUB14632MIG
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
DRUG BANK
DBSALT001027
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
PUBCHEM
11812257
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
RXCUI
236883
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY RxNorm
DAILYMED
JGS34J7L9I
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
CAS
152520-56-4
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL434394
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
CHEBI
132912
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
MESH
C052753
Created by admin on Wed Jul 05 23:20:37 UTC 2023 , Edited by admin on Wed Jul 05 23:20:37 UTC 2023
PRIMARY
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