Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C22H25F2NO4 |
| Molecular Weight | 405.435 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[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=KOHIRBRYDXPAMZ-YHBROIRLSA-N
InChI=1S/C22H25F2NO4/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/t17-,18-,21-,22+/m1/s1
| 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 |
DescriptionSources: https://www.drugbank.ca/drugs/DB04861 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021742s000_LBL.pdf | http://www.bystolic.com/https://www.drugbank.ca/drugs/DB04861 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021742s000_LBL.pdf | https://www.ncbi.nlm.nih.gov/pubmed/18485134 | https://www.ncbi.nlm.nih.gov/pubmed/9825177 | https://www.ncbi.nlm.nih.gov/pubmed/21283024 | https://www.ncbi.nlm.nih.gov/pubmed/1681809 | https://www.ncbi.nlm.nih.gov/pubmed/1357130
Sources: https://www.drugbank.ca/drugs/DB04861 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021742s000_LBL.pdf | http://www.bystolic.com/https://www.drugbank.ca/drugs/DB04861 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021742s000_LBL.pdf | https://www.ncbi.nlm.nih.gov/pubmed/18485134 | https://www.ncbi.nlm.nih.gov/pubmed/9825177 | https://www.ncbi.nlm.nih.gov/pubmed/21283024 | https://www.ncbi.nlm.nih.gov/pubmed/1681809 | https://www.ncbi.nlm.nih.gov/pubmed/1357130
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.
CNS Activity
Sources: https://link.springer.com/article/10.1007/BF03258299 | https://books.google.ru/books?id=2Q5hCgAAQBAJ&pg=PA188&lpg=PA188&dq=nebivolol retrieved from Pharmacotherapeutics For Advanced Practice Nurse Prescribers By Teri Moser Woo, Marylou V Robinson, p.188 | https://www.ncbi.nlm.nih.gov/pubmed/23128558https://link.springer.com/article/10.1007/BF03258299 | https://books.google.ru/books?id=2Q5hCgAAQBAJ&pg=PA188&lpg=PA188&dq=nebivolol retrieved from Pharmacotherapeutics For Advanced Practice Nurse Prescribers By Teri Moser Woo, Marylou V Robinson, p.188
Curator's Comment: Nebivolol is a highly lipophilic drug and, thus, it may penetrate the central nervous system (CNS) in humans.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 0.7 nM [Ki] | |||
| 0.35 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | BYSTOLIC Approved UseBYSTOLIC 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 Date1.19784958E12 |
|||
| Primary | BYSTOLIC Approved UseBYSTOLIC 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 Date1.1977632E12 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2% |
unknown |
NEBIVOLOL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse 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 Sources: Page: p.8Pallor Depressed level of consciousness Hypokinesia Hypotension Sinus bradycardia Hypoglycemia Hypokalemia Respiratory failure Vomiting |
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%) Sources: Page: p.4Nausea (0.2%) Bradycardia (0.2%) |
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
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 28, 50, 55 |
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
| Title | Date | PubMed |
|---|---|---|
| Effects of D-nebivolol and L-nebivolol on left ventricular systolic and diastolic function: comparison with D-L-nebivolol and atenolol. | 1993 Aug |
|
| Nebivolol: comparison of the effects of dl-nebivolol, d-nebivolol, l-nebivolol, atenolol, and placebo on exercise-induced increases in heart rate and systolic blood pressure. | 1998 Sep |
|
| Beta-blockade with nebivolol enhances the acetylcholine-induced cutaneous vasodilation. | 2001 Apr |
|
| Nebivolol, bucindolol, metoprolol and carvedilol are devoid of intrinsic sympathomimetic activity in human myocardium. | 2001 Aug |
|
| Vascular effects of newer cardiovascular drugs: focus on nebivolol and ACE-inhibitors. | 2001 Dec |
|
| Protective role of nebivolol in hydroxyl radical induced injury. | 2001 Dec |
|
| Nebivolol: endothelium-mediated vasodilating effect. | 2001 Dec |
|
| [Heart and lung disease. Are beta blockers allowed in asthma?]. | 2001 May 24 |
|
| [Pharma-clinics medication of the month. Nebivolol (Nobiten)]. | 2001 Nov |
|
| Endothelial adrenoceptors. | 2001 Nov |
|
| [Beta blockers in heart failure administered with too much reticence. Longevity sacrificed]. | 2001 Nov 29 |
|
| [Nebivolol (nebilet) a beta blocker of the third generation--also for patients with obstructive lung diseases?]. | 2001 Oct |
|
| What drug must be used to avoid the most common hypertensive complications? | 2001 Oct |
|
| [Antihypertensive efficacy and tolerability of nebivolol]. | 2002 |
|
| Nebivolol vs amlodipine as first-line treatment of essential arterial hypertension in the elderly. | 2002 |
|
| Paradoxical pressor effects of beta-blockers in standing elderly patients with mild hypertension: a beneficial side effect. | 2002 Apr 9 |
|
| 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 |
|
| Hyperkalaemia in an elderly diabetic patient. | 2002 Jan |
|
| The pharmacologic treatment of uncomplicated arterial hypertension in patients with airway dysfunction. | 2002 Jan |
|
| [Cardiac protection by beta-1 selective beta blocker. Still better in the 3rd generation?]. | 2002 Jul 11 |
|
| Effects of nebivolol and atenolol on small arteries and microcirculatory endothelium-dependent dilation in hypertensive patients undergoing isometric stress. | 2002 Sep |
|
| Focus on small artery stiffness. | 2002 Sep |
|
| [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 |
|
| 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 |
|
| 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 |
|
| [Beta-1 blockade plus NO release. Additional organ protection for patients with hypertension]. | 2003 Oct 2 |
|
| [Nebivolol in the treatment of ischemic heart disease patients with chronic heart failure]. | 2004 |
|
| Antioxidant activity of nebivolol in the rat aorta. | 2004 Jan |
|
| Different pharmacological properties of two enantiomers in a unique beta-blocker, nebivolol. | 2008 Summer |
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
Edited
Wed Jul 05 23:09:50 UTC 2023
by
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on
Wed Jul 05 23:09:50 UTC 2023
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| Record UNII |
030Y90569U
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| Record Status |
Validated (UNII)
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LIVERTOX |
NBK548386
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NDF-RT |
N0000175556
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WHO-VATC |
QC07AB12
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WHO-ATC |
C07FB12
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WHO-ATC |
C09DX05
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NCI_THESAURUS |
C29576
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C07BB12
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C07AB12
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WHO-VATC |
QC07BB12
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100000093044
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1887
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DB04861
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C66221
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M7786
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Y-62
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030Y90569U
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CHEMBL434394
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Nebivolol
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C052753
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NEBIVOLOL
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118457-14-0
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TARGET -> AGONIST |
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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