Details
Stereochemistry | RACEMIC |
Molecular Formula | C22H25F2NO4 |
Molecular Weight | 405.4358 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C1C[C@]([H])([C@@]([H])(CNC[C@]([H])([C@]2([H])CCc3cc(ccc3O2)F)O)O)Oc4ccc(cc14)F
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 | 405.4358 |
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 | 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/1357130https://www.drugbank.ca/drugs/DB04861 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021742s000_LBL.pdf | http://www.bystolic.com/
Sources: 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/1357130https://www.drugbank.ca/drugs/DB04861 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021742s000_LBL.pdf | http://www.bystolic.com/
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.
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.188https://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/23128558
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] | |||
Target ID: CHEMBL213 |
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 |
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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 |
---|---|---|---|---|
Page: 50, 55 |
no | |||
Page: 50, 55 |
no | |||
Page: 50, 55 |
no | |||
Page: 50, 55 |
no | |||
Page: 50, 55 |
no | |||
Page: 50, 55 |
no | |||
Page: 50, 55 |
no | |||
Page: 50, 55 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 28, 50, 55 |
minor | |||
Page: 17.0 |
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 |
|
[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 |
|
[Assessment of safety and antihypertensive efficacy of a cardioselective beta-blocker nebivolol in patients with hypertension and concomitant chronic obstructive bronchitis]. | 2002 |
|
[Antihypertensive efficacy and tolerability of nebivolol]. | 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 |
|
[Cardiac protection by beta-1 selective beta blocker. Still better in the 3rd generation?]. | 2002 Jul 11 |
|
[Despite antihypertensive treatment with beta-blocker patients remain incapacitated]. | 2002 May 2 |
|
Nebivolol inhibits vascular smooth muscle cell proliferation by mechanisms involving nitric oxide but not cyclic GMP. | 2002 Sep |
|
Nebivolol: a selective beta(1)-adrenergic receptor antagonist that relaxes vascular smooth muscle by nitric oxide- and cyclic GMP-dependent mechanisms. | 2002 Sep |
|
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 |
|
[Nebivolol effects on platelet aggregation and anticoagulation system]. | 2003 |
|
[Dynamics of a 24-h profile of arterial pressure and function of the vascular endothelium in nebivolol treatment of hypertensive patients]. | 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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
Different pharmacological properties of two enantiomers in a unique beta-blocker, nebivolol. | 2008 Summer |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7596131
After a 4-week placebo run-in period, 30 patients (mean age 48 years) were randomly allocated to double-blind treatment with either DL-nebivolol 5 mg or D-nebivolol 2.5 mg once daily for 4 weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2575531
Nebivolol and d-nebivolol (SRRR) inhibited noradrenaline-induced cAMP accumulation with IC50 values of 22 and 15 nM, respectively in rat living cardiac cells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 09:33:10 UTC 2021
by
admin
on
Sat Jun 26 09:33:10 UTC 2021
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Record UNII |
030Y90569U
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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LIVERTOX |
672
Created by
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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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WHO-ATC |
C07BB12
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WHO-ATC |
C07AB12
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WHO-VATC |
QC07BB12
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Code System | Code | Type | Description | ||
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1887
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PRIMARY | |||
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DB04861
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PRIMARY | |||
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C66221
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PRIMARY | |||
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M7786
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PRIMARY | Merck Index | ||
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SUB09175MIG
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030Y90569U
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CHEMBL434394
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Nebivolol
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7246
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99200-09-6
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NON-SPECIFIC STEREOCHEMISTRY | |||
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31555
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PRIMARY | RxNorm | ||
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C052753
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NEBIVOLOL
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99200-09-6
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5969
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118457-14-0
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TARGET -> AGONIST |
SHORT-ACTING
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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IN THE EM POPULATION |
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Biological Half-life | PHARMACOKINETIC |
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