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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
Structure of NEBIVOLOL

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

HIDE SMILES / InChI

Molecular Formula C22H25F2NO4
Molecular Weight 405.435
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.7 nM [Ki]
0.35 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BYSTOLIC
Primary
BYSTOLIC

Cmax

ValueDoseCo-administeredAnalytePopulation
1.48 ng/mL
10 mg single, oral
NEBIVOLOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
7.76 ng × h/mL
10 mg single, oral
NEBIVOLOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11 h
10 mg single, oral
NEBIVOLOL plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
unknown
NEBIVOLOL plasma
Homo sapiens

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
030Y90569U
Record Status Validated (UNII)
Record Version