Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H25F2NO4 |
Molecular Weight | 405.435 |
Optical Activity | UNSPECIFIED |
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=CC(F)=CC=C4O3
InChI
InChIKey=KOHIRBRYDXPAMZ-YHDSQAASSA-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+/m0/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 |
Marketed under the brand name BYSTOLIC, Nebivolol is indicated for
the treatment of hypertension, to lower blood pressure. Nebivolol is a racemic mixture containing equal amounts of two enantiomers, d-nebivolol and l-nebivolol (Levonebivolol). It is a selective β1-adrenergic antagonist with vasodilating properties. The d-enantiomer provides selective β1-adrenergic receptor blockade, whereas l-nebivolol possesses vasodilating properties thought to be attributable to nitric oxide modulation via the L-argininenitric oxide pathway. dl-nebivolol exerts an antithrombotic activity by stimulating the formation of NO by platelets, and that this effect is generated by its l-enantiomer, whereas the d-enantiomer exerts a weak antiplatelet effect because of β-adrenergic receptor-independent stimulation of adenyly cyclase. L-nebivolol had a protective effect against both endothelial dysfunction of the mesenteric artery and ileal injury induced by intestinal I/R; however, similar effects were not observed for racemic nebivolol. 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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL4031 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19210511 |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/7596131 https://www.ncbi.nlm.nih.gov/pubmed/7692155 https://www.ncbi.nlm.nih.gov/pubmed/18485134 https://www.ncbi.nlm.nih.gov/pubmed/1357130 https://allergan-web-cdn-prod.azureedge.net/allergancanadaspecialty/allergancanadaspecialty/media/actavis-canada-specialty/en/products/pms/2016-06-16-bystolic-pm_english_clean.pdf |
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 Date2007 |
PubMed
Title | Date | PubMed |
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Nebivolol: a novel beta-blocker with nitric oxide-induced vasodilatation. | 2006 |
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Different pharmacological properties of two enantiomers in a unique beta-blocker, nebivolol. | 2008 Summer |
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Nebivolol has protective effect against endothelial and ileal dysfunction due to I/R. | 2011 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9825177
The effects of racemic nebivolol, 2.5, 5.0, and 10.0 mg; d-nebivolol, 2.5 mg; l-nebivolol, 2.5 mg; atenolol, 50 mg; and placebo, each given once daily for 7 days, on exercise-induced increases in heart rate and systolic blood pressure were compared in a seven-way double-blind randomized crossover trial in 14 healthy male volunteers.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12512696
Curator's Comment: D-nebivolol (0.1-10 uM/L), but not L-nebivolol (0.1-10 uM/L), significantly shifted to the right the concentration-response curve to phenylephrine, an alpha(1)-adrenoceptor agonist, in a concentration-dependent manner. https://www.ncbi.nlm.nih.gov/pubmed/19210511
In the isolated guinea pig heart coronary vasodilator potency of L- and D-nebivolol and a possible role of beta2, beta3 adrenoceptors and 5-HT1A receptors in nebivolol-induced vasodilation was analysed. Not only L-nebivolol (3-30 x 10(-6) M) but also D-nebivolol (3-30 x 10(-6) M) induced coronary vasodilation, and both responses were inhibited by L-NAME (10(-4) M).
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 17:26:41 GMT 2023
by
admin
on
Fri Dec 15 17:26:41 GMT 2023
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GMK2E335DQ
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Validated (UNII)
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C29576
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BINDER->LIGAND |
BINDING
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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blood-to-plasma ratio | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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IN THE PM POPULATION |
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