What Is Nebivolol 5 Mg Used for

Nebivolol

Summary

Nebivolol is a beta blocking agent used to treat hypertension and aid in the management of heart failure.

Brand Names

Bystolic

Generic Name

Nebivolol

DrugBank Accession Number

DB04861

Background

Nebivolol is a racemic mixture of 2 enantiomers where one is a beta adrenergic antagonist and the other acts as a cardiac stimulant without beta adrenergic activity.² Treatment with nebivolol leads to a greater decrease in systolic and diastolic blood pressure than atenolol, propranolol, or pindolol.² Nebivolol and other beta blockers are generally not first line therapies as many patients are first treated with thiazide diuretics.[A182594]

Nebivolol was granted FDA approval on 17 December 2007.⁸

Type

Small Molecule

Groups

Approved, Investigational

Structure

Weight: Average: 405.435
Monoisotopic: 405.175164703
Chemical Formula: C₂₂H₂₅F₂NO₄

Synonyms

Narbivolol
Nebivolol
Nebivololum

External IDs

PI-21858
R-65824
R65,824

Indication

Nebivolol is indicated to treat hypertension.^1,2,8,9

Pharmacology

Reduce drug development failure rates

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Associated Conditions

High Blood Pressure (Hypertension)

Contraindications & Blackbox Warnings

Contraindications

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Pharmacodynamics

Nebivolol is a selective beta-1 adrenergic receptor antagonist that decreases vascular resistance, increases stroke volume and cardiac output, and does not negatively affect left ventricular function.^2,3 It has a long duration of action as effects can be seen 48 hours after stopping the medication and a wide therapeutic window as patients generally take 5-40mg daily.^2,8 Patients should not abruptly stop taking this medication as this may lead to exacerbation of coronary artery disease.⁸ Diabetic patients should monitor their blood glucose levels as beta blockers may mask signs of hypoglycemia.⁸

Mechanism of action

Nebivolol is a highly selective beta-1 adrenergic receptor antagonist² with weak beta-2 adrenergic receptor antagonist activity.³ Blocking beta-1 adrenergic receptors by d-nebivolol leads to decreased resting heart rate, exercise heart rate, myocardial contracility, systolic blood pressure, and diastolic blood pressure.^4,2,3,5 The selectivity of d-nebivolol limits the magnitude of beta blocker adverse effects in the airways or relating to insulin sensitivity.⁵ Nebivolol also inhibits aldosterone, and beta-1 antagonism in the juxtaglomerular apparatus also inhibits the release of renin.⁵ Decreased aldosterone leads to decreased blood volume, and decreased renin leads to reduced vasoconstriction.⁵ l-nebivolol is responsible for beta-3 adrenergic receptor agonist activity that stimulates endothelial nitric oxide synthase, increasing nitric oxide levels; leading to vasodilation, decreased peripheral vascular resistance, increased stroke volume, ejection fraction, and cardiac output.^1,4,2,3,5 The vasodilation, reduced oxidative stress, and reduced platelet volume and aggregation of nebivolol may lead to benefits in heart failure patients.⁴

Target	Actions	Organism
ABeta-1 adrenergic receptor	antagonist	Humans
UBeta-2 adrenergic receptor	antagonist	Humans
UBeta-3 adrenergic receptor	agonist	Humans

Absorption

The absorption of nebivolol is not affected by food.⁸ Nebivolol has a T_max of 1.5-4 hours.⁸ Bioavailability can range from 12-96% for extensive to poor CYP2D6 metabolizers.^6,7 For a 20mg dose, d-nebivolol has a C_max of 2.75±1.55ng/mL, l-nebivolol has a C_max of 5.29±2.06ng/mL, both enantiomers have a C_max of 8.02±3.47ng/mL, and nebivolol glucuronides have a C_max of 68.34±44.68ng/mL.⁶ For a 20mg dose, d-nebivolol has an AUC of 13.78±15.27ng*h/mL, l-nebivolol has an AUC of 27.72±15.32ng*h/mL, both enantiomers have an AUC of 41.50±29.76ng*h/mL, and nebivolol glucuronides have an AUC of 396.78±297.94ng*h/mL.⁶

Volume of distribution

For a 20mg dose, d-nebivolol has an apparent volume of distribution of 10,290.81±3911.72L, l-nebivolol has an apparent volume of distribution of 8,066.66±4,055.50L, and both enantiomers together have a volume of distribution of 10,423.42±6796.50L.⁶

Protein binding

Nebivolol is 98% bound to plasma proteins, mostly to serum albumin.⁸

Metabolism

Nebivolol is metabolized mainly by glucuronidation and CYP2D6 mediated hydroxylation.^1,4 Metabolism involves n-dealkylation, hydroxylation, oxidation, and glucuronidation.⁷ Aromatic hydroxyl and acyclic oxide metabolites are active, while n-dealkylated and glucuronides are inactive.⁷

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Route of elimination

In extensive CYP2D6 metabolizers, 38% is eliminated in the urine and 44% in the feces.⁸ In poor CYP2D6 metabolizers, 67% is eliminated in the urine and 13% in the feces.⁸ <1% of a dose is excreted as the unmetabolized drug.⁵

Half-life

d-nebivolol has a half life of 12 hours in CYP2D6 extensive metabolizers and 19 hours in poor metabolizers.^5,8

Clearance

For a 20mg dose, the clearance of d-nebivolol is 1241.63±749.77L/h, l-nebivolol is 435.53±180.93L/h, and both enantiomers is 635.31±300.25L/h.⁶

Adverse Effects

Adverseeffects

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Toxicity

Patients experiencing an overdose may present with bradycardia, hypotension, cardiac failure, dizziness, hypoglycemia, fatigue, vomiting, bronchospasm and heart block.⁸ Treat overdose with general supportive measures including intravenous atropine for bradycardia, vasopressors and intravenous fluids for hypotension, isoproterenol infusion for heart block, digitalis glycosides and diuretics for congestive heart failure, bronchodilators for bronchospasm, and intravenous glucose for hypoglycemia.⁸

Pathways

Pathway	Category
Nebivolol Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Cytochrome P450 2D6	CYP2D6*3	Not Available	C allele	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*4	Not Available	C allele	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*5	Not Available	Whole-gene deletion	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*6	Not Available	1707delT	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*7	Not Available	2935A>C	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*8	Not Available	1758G>T	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*11	Not Available	883G>C	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*12	Not Available	124G>A	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*13	Not Available	CYP2D7/2D6 hybrid gene structure	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*14A	Not Available	1758G>A	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*15	Not Available	137insT, 137_138insT	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*19	Not Available	2539_2542delAACT	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*20	Not Available	1973_1974insG	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*21	Not Available	2573insC	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*31	Not Available	-1770G>A / -1584C>G … show all	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*36	Not Available	100C>T / -1426C>T … show all	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*38	Not Available	2587_2590delGACT	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*40	Not Available	1863_1864ins(TTT CGC CCC)2	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*42	Not Available	3259_3260insGT	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*44	Not Available	2950G>C	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*47	Not Available	100C>T / -1426C>T … show all	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*51	Not Available	-1584C>G / -1235A>G … show all	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*56	Not Available	3201C>T	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*57	Not Available	100C>T / 310G>T … show all	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*62	Not Available	4044C>T	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*68A	Not Available	-1426C>T / -1235A>G … show all	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*68B	Not Available	Similar but not identical switch region compared to CYP2D668A. Found in tandem arrangement with CYP2D64.	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*69	Not Available	2988G>A / -1426C>T … show all	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*92	Not Available	1995delC	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*100	Not Available	-1426C>T / -1235A>G … show all	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2D6	CYP2D6*101	Not Available	-1426C>T / -1235A>G … show all	Effect Inferred	Poor drug metabolizer.	Details

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Approved
Vet approved
Nutraceutical
Illicit
Withdrawn
Investigational
Experimental
All Drugs

Drug	Interaction
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Abametapir	The serum concentration of Nebivolol can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Nebivolol can be increased when combined with Abatacept.
Abiraterone	The metabolism of Nebivolol can be decreased when combined with Abiraterone.
Acarbose	The therapeutic efficacy of Acarbose can be increased when used in combination with Nebivolol.
Acebutolol	Acebutolol may increase the arrhythmogenic activities of Nebivolol.
Aceclofenac	Aceclofenac may decrease the antihypertensive activities of Nebivolol.
Acemetacin	Acemetacin may decrease the antihypertensive activities of Nebivolol.
Acenocoumarol	The metabolism of Nebivolol can be decreased when combined with Acenocoumarol.
Acetaminophen	The metabolism of Nebivolol can be decreased when combined with Acetaminophen.
Acetohexamide	The therapeutic efficacy of Acetohexamide can be increased when used in combination with Nebivolol.

Food Interactions

Avoid alcohol.
Take with or without food.

Products2

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Nebivolol hydrochloride	JGS34J7L9I	152520-56-4	JWEXHQAEWHKGCW-VCVZPGOSSA-N

Product Images

International/Other Brands

Lobivon / Nebicard / Nebilet / Nebilong / Nodon / Nubeta

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Bystolic	Tablet	5 mg/1	Oral	Cardinal Health	2008-01-22	2023-06-30
Bystolic	Tablet	5 mg/1	Oral	Physicians Total Care, Inc.	2008-10-02	Not applicable
Bystolic	Tablet	10 mg/1	Oral	Allergan, Inc.	2008-01-22	Not applicable
Bystolic	Tablet	10 mg	Oral	Allergan	2013-04-02	Not applicable
Bystolic	Tablet	2.5 mg/1	Oral	Med Pharma Co., Ltd.	2011-06-01	2012-06-21
Bystolic	Tablet	5 mg/1	Oral	A-S Medication Solutions	2008-01-22	Not applicable
Bystolic	Tablet	20 mg/1	Oral	Cardinal Health	2008-01-22	2023-06-30
Bystolic	Tablet	5 mg/1	Oral	Avera McKennan Hospital	2015-03-19	2017-05-24
Bystolic	Tablet	20 mg/1	Oral	Med Pharma Co., Ltd.	2011-06-01	2012-06-21
Bystolic	Tablet	10 mg/1	Oral	A-S Medication Solutions	2008-01-22	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-nebivolol	Tablet	5 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Apo-nebivolol	Tablet	2.5 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Apo-nebivolol	Tablet	20 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Nebivolol	Tablet	20 mg/1	Oral	Glenmark Pharmaceuticals Inc., USA	2017-05-25	Not applicable
Nebivolol	Tablet	5 mg/1	Oral	A-S Medication Solutions	2021-09-16	Not applicable
Nebivolol	Tablet	2.5 mg/1	Oral	Amerigen Pharmaceuticals Inc.	2015-04-28	Not applicable
Nebivolol	Tablet	5 mg/1	Oral	Ascend Laboratories, LLC	2021-09-16	Not applicable
Nebivolol	Tablet	10 mg/1	Oral	Camber Pharmaceuticals, Inc.	2021-09-17	Not applicable
Nebivolol	Tablet	20 mg/1	Oral	ANI Pharmaceuticals, Inc.	2021-09-17	Not applicable
Nebivolol	Tablet	2.5 mg/1	Oral	A-S Medication Solutions	2021-09-16	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
AMLONEB 10 MG/10 MG TABLET, 30 ADET	Nebivolol hydrochloride (10 mg) + Amlodipine besylate (10 mg)	Tablet	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2020-08-14	Not applicable
AMLONEB 10 MG/10 MG TABLET, 90 ADET	Nebivolol hydrochloride (10 mg) + Amlodipine besylate (10 mg)	Tablet	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2020-08-14	Not applicable
AMLONEB 10 MG/2.5 MG TABLET, 30 ADET	Nebivolol hydrochloride (2.5 mg) + Amlodipine besylate (10 mg)	Tablet	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2020-08-14	Not applicable
AMLONEB 10 MG/2.5 MG TABLET, 90 ADET	Nebivolol hydrochloride (2.5 mg) + Amlodipine besylate (10 mg)	Tablet	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2020-08-14	Not applicable
AMLONEB 10 MG/5 MG TABLET, 30 ADET	Nebivolol hydrochloride (5 mg) + Amlodipine besylate (10 mg)	Tablet	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2020-08-14	Not applicable
AMLONEB 10 MG/5 MG TABLET, 90 ADET	Nebivolol hydrochloride (5 mg) + Amlodipine besylate (10 mg)	Tablet	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2020-08-14	Not applicable
AMLONEB 5 MG/10 MG TABLET, 30 ADET	Nebivolol hydrochloride (10 mg) + Amlodipine besylate (5 mg)	Tablet	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2020-08-14	Not applicable
AMLONEB 5 MG/10 MG TABLET, 90 ADET	Nebivolol hydrochloride (10 mg) + Amlodipine besylate (5 mg)	Tablet	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2020-08-14	Not applicable
AMLONEB 5 MG/2.5 MG TABLET, 30 ADET	Nebivolol hydrochloride (2.5 mg) + Amlodipine besylate (5 mg)	Tablet	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2020-08-14	Not applicable
AMLONEB 5 MG/2.5 MG TABLET, 90 ADET	Nebivolol hydrochloride (2.5 mg) + Amlodipine besylate (5 mg)	Tablet	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2020-08-14	Not applicable

ATC Codes

C07FB12 — Nebivolol and amlodipine

C07FB — Beta blocking agents and calcium channel blockers
C07F — BETA BLOCKING AGENTS, OTHER COMBINATIONS
C07 — BETA BLOCKING AGENTS
C — CARDIOVASCULAR SYSTEM

C09DX05 — Valsartan and nebivolol

C09DX — Angiotensin II receptor blockers (ARBs), other combinations
C09D — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS
C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
C — CARDIOVASCULAR SYSTEM

C07BB12 — Nebivolol and thiazides

C07BB — Beta blocking agents, selective, and thiazides
C07B — BETA BLOCKING AGENTS AND THIAZIDES
C07 — BETA BLOCKING AGENTS
C — CARDIOVASCULAR SYSTEM

C07AB12 — Nebivolol

C07AB — Beta blocking agents, selective
C07A — BETA BLOCKING AGENTS
C07 — BETA BLOCKING AGENTS
C — CARDIOVASCULAR SYSTEM

Drug Categories

Adrenergic Agents
Adrenergic Agonists
Adrenergic Antagonists
Adrenergic beta-1 Receptor Agonists
Adrenergic beta-Agonists
Adrenergic beta-Antagonists
Agents causing hyperkalemia
Alcohols
Amines
Amino Alcohols
Antiarrhythmic agents
Antihypertensive Agents
Antihypertensive Agents Indicated for Hypertension
Benzopyrans
Beta blocking agents and calcium channel blockers
Beta Blocking Agents and Thiazides
Beta Blocking Agents, Selective
Beta Blocking Agents, Selective, and Thiazides
Beta-Blockers (Beta1 Selective)
Bradycardia-Causing Agents
Cardiovascular Agents
Cytochrome P-450 CYP2C19 Substrates
Cytochrome P-450 CYP2D6 Substrates
Cytochrome P-450 CYP3A Substrates
Cytochrome P-450 CYP3A4 Substrates
Cytochrome P-450 Substrates
Ethanolamines
Heterocyclic Compounds, Fused-Ring
Hypotensive Agents
Neurotransmitter Agents
Pyrans
Vasodilating Agents

Chemical TaxonomyProvided by Classyfire

Description: This compound belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
Kingdom: Organic compounds
Super Class: Organoheterocyclic compounds
Class: Benzopyrans
Sub Class: 1-benzopyrans
Direct Parent: 1-benzopyrans
Alternative Parents: Aralkylamines / Alkyl aryl ethers / Benzenoids / Aryl fluorides / Secondary alcohols / 1,2-aminoalcohols / Oxacyclic compounds / Dialkylamines / Organopnictogen compounds / Organofluorides / Hydrocarbon derivatives show 1 more
Substituents: 1,2-aminoalcohol / 1-benzopyran / Alcohol / Alkyl aryl ether / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Benzenoid / Ether / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organofluoride / Organohalogen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Secondary alcohol / Secondary aliphatic amine / Secondary amine show 13 more
Molecular Framework: Aromatic heteropolycyclic compounds
External Descriptors: organofluorine compound, secondary alcohol, secondary amino compound, diol, chromanes (CHEBI:64019)

Affected organisms

Humans and other mammals

UNII: 030Y90569U
CAS number: 118457-14-0
InChI Key: KOHIRBRYDXPAMZ-UHFFFAOYSA-N
InChI: 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
IUPAC Name: 1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-{[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyethyl]amino}ethan-1-ol
SMILES: OC(CNCC(O)C1CCC2=C(O1)C=CC(F)=C2)C1CCC2=C(O1)C=CC(F)=C2

Synthesis Reference

Thomas Bader, Alfred Stutz, Harald Hofmeier, Hans-Ulrich Bichsel, "Process for preparation of racemic Nebivolol." U.S. Patent US20070149612, issued June 28, 2007.

US20070149612

General References

Gielen W, Cleophas TJ, Agrawal R: Nebivolol: a review of its clinical and pharmacological characteristics. Int J Clin Pharmacol Ther. 2006 Aug;44(8):344-57. [Article]
De Cree J, Cobo C, Geukens H, Verhaegen H: Comparison of the subacute hemodynamic effects of atenolol, propranolol, pindolol, and nebivolol. Angiology. 1990 Feb;41(2):95-105. doi: 10.1177/000331979004100202. [Article]
Van de Water A, Janssens W, Van Neuten J, Xhonneux R, De Cree J, Verhaegen H, Reneman RS, Janssen PA: Pharmacological and hemodynamic profile of nebivolol, a chemically novel, potent, and selective beta 1-adrenergic antagonist. J Cardiovasc Pharmacol. 1988 May;11(5):552-63. doi: 10.1097/00005344-198805000-00007. [Article]
Fongemie J, Felix-Getzik E: A Review of Nebivolol Pharmacology and Clinical Evidence. Drugs. 2015 Aug;75(12):1349-71. doi: 10.1007/s40265-015-0435-5. [Article]
Giles TD, Cockcroft JR, Pitt B, Jakate A, Wright HM: Rationale for nebivolol/valsartan combination for hypertension: review of preclinical and clinical data. J Hypertens. 2017 Sep;35(9):1758-1767. doi: 10.1097/HJH.0000000000001412. [Article]
Chen CL, Desai-Krieger D, Ortiz S, Kerolous M, Wright HM, Ghahramani P: A Single-Center, Open-Label, 3-Way Crossover Trial to Determine the Pharmacokinetic and Pharmacodynamic Interaction Between Nebivolol and Valsartan in Healthy Volunteers at Steady State. Am J Ther. 2015 Sep-Oct;22(5):e130-40. doi: 10.1097/MJT.0000000000000247. [Article]
Briciu C, Neag M, Muntean D, Bocsan C, Buzoianu A, Antonescu O, Gheldiu AM, Achim M, Popa A, Vlase L: Phenotypic differences in nebivolol metabolism and bioavailability in healthy volunteers. Clujul Med. 2015;88(2):208-13. doi: 10.15386/cjmed-395. Epub 2015 Apr 15. [Article]
FDA Approved Drug Products: Nebivolol Tablets [Link]
FDA Approved Drug Products: Nebivolol and Valsartan Tablets [Link]

External Links

Human Metabolome Database: HMDB0015594
KEGG Drug: D05127
PubChem Compound: 71301
PubChem Substance: 99443225
ChemSpider: 64421
BindingDB: 84735
RxNav: 31555
ChEBI: 64019
ChEMBL: CHEMBL434394
Therapeutic Targets Database: DAP000942
PharmGKB: PA151958426
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Nebivolol

MSDS

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Basic Science	Aortic Blood Pressure	1
4	Completed	Basic Science	Syndrome, Metabolic	1
4	Completed	Diagnostic	High Blood Pressure (Hypertension)	2
4	Completed	Health Services Research	JNC 7 Stage 1 or 2 Hypertension	1
4	Completed	Other	High Blood Pressure (Hypertension) / Prehypertension	2
4	Completed	Prevention	Blood Pressures / Hypertension Complicated / Left Ventricular Hypertrophy	1
4	Completed	Treatment	Altitude / Heart Failure / Hypoxia	1
4	Completed	Treatment	Arteriospasm coronary	1
4	Completed	Treatment	Atherosclerosis / Flow-mediated Vasodilatation (FMD)	1
4	Completed	Treatment	Chronic Heart Failure (CHF)	1

Manufacturers

Not Available

Packagers

Forest Laboratories Inc.
Forest Pharmaceuticals
Mylan
Physicians Total Care Inc.

Dosage Forms

Form	Route	Strength
Tablet	Oral
Tablet	Oral	10 mg
Tablet	Oral	10 mg/1
Tablet	Oral	2.5 mg/1
Tablet	Oral	2.5 mg
Tablet	Oral	20 mg
Tablet	Oral	20 mg/1
Tablet	Oral	5 mg/1
Tablet, film coated	Oral
Tablet	Oral
Tablet, film coated	Oral
Tablet, coated	Oral
Tablet, coated
Tablet	Oral	5 mg

Prices

Unit description	Cost	Unit
Bystolic 10 mg tablet	2.09USD	tablet
Bystolic 20 mg tablet	2.09USD	tablet
Bystolic 2.5 mg tablet	2.06USD	tablet
Bystolic 5 mg tablet	2.06USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5759580	No	1998-06-02	2015-06-02
US6545040	No	2003-04-08	2021-12-17
US7803838	No	2010-09-28	2026-08-29
US7838552	No	2010-11-23	2027-10-04

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	223.0-228.0	https://www.tcichemicals.com/eshop/en/gb/commodity/N0954/
water solubility	0.091g/100mL	http://www.medicines.org.au/files/txpnebiv.pdf
logP	4.183	https://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=CA&language=en&productNumber=N1915&brand=SIGMA&PageToGoToURL=https%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Fsigma%2Fn1915%3Flang%3Den
pKa	8.13	http://www.medicines.org.au/files/txpnebiv.pdf

Predicted Properties

Property	Value	Source
Water Solubility	0.0403 mg/mL	ALOGPS
logP	2.44	ALOGPS
logP	3.21	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.52	ChemAxon
pKa (Strongest Basic)	8.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	70.95 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.32 m³·mol^-1	ChemAxon
Polarizability	41.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.8483
Blood Brain Barrier	+	0.7802
Caco-2 permeable	-	0.5549
P-glycoprotein substrate	Substrate	0.7928
P-glycoprotein inhibitor I	Non-inhibitor	0.7443
P-glycoprotein inhibitor II	Non-inhibitor	0.567
Renal organic cation transporter	Non-inhibitor	0.8016
CYP450 2C9 substrate	Non-substrate	0.8738
CYP450 2D6 substrate	Non-substrate	0.7248
CYP450 3A4 substrate	Non-substrate	0.6822
CYP450 1A2 substrate	Inhibitor	0.5145
CYP450 2C9 inhibitor	Non-inhibitor	0.7876
CYP450 2D6 inhibitor	Non-inhibitor	0.5994
CYP450 2C19 inhibitor	Non-inhibitor	0.5923
CYP450 3A4 inhibitor	Non-inhibitor	0.9441
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8336
Ames test	Non AMES toxic	0.7132
Carcinogenicity	Non-carcinogens	0.9402
Biodegradation	Not ready biodegradable	0.9953
Rat acute toxicity	2.7228 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Strong inhibitor	0.5769
hERG inhibition (predictor II)	Inhibitor	0.8381

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

Drugtargets2

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Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Receptor signaling protein activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name: ADRB1
Uniprot ID: P08588
Uniprot Name: Beta-1 adrenergic receptor
Molecular Weight: 51322.1 Da

References

Gielen W, Cleophas TJ, Agrawal R: Nebivolol: a review of its clinical and pharmacological characteristics. Int J Clin Pharmacol Ther. 2006 Aug;44(8):344-57. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
de Boer RA, Voors AA, van Veldhuisen DJ: Nebivolol: third-generation beta-blockade. Expert Opin Pharmacother. 2007 Jul;8(10):1539-50. [Article]

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Protein homodimerization activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name: ADRB2
Uniprot ID: P07550
Uniprot Name: Beta-2 adrenergic receptor
Molecular Weight: 46458.32 Da

References

Nuttall SL, Routledge HC, Kendall MJ: A comparison of the beta1-selectivity of three beta1-selective beta-blockers. J Clin Pharm Ther. 2003 Jun;28(3):179-86. [Article]

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Protein homodimerization activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name: ADRB3
Uniprot ID: P13945
Uniprot Name: Beta-3 adrenergic receptor
Molecular Weight: 43518.615 Da

References

Gielen W, Cleophas TJ, Agrawal R: Nebivolol: a review of its clinical and pharmacological characteristics. Int J Clin Pharmacol Ther. 2006 Aug;44(8):344-57. [Article]
Fongemie J, Felix-Getzik E: A Review of Nebivolol Pharmacology and Clinical Evidence. Drugs. 2015 Aug;75(12):1349-71. doi: 10.1007/s40265-015-0435-5. [Article]
De Cree J, Cobo C, Geukens H, Verhaegen H: Comparison of the subacute hemodynamic effects of atenolol, propranolol, pindolol, and nebivolol. Angiology. 1990 Feb;41(2):95-105. doi: 10.1177/000331979004100202. [Article]
Van de Water A, Janssens W, Van Neuten J, Xhonneux R, De Cree J, Verhaegen H, Reneman RS, Janssen PA: Pharmacological and hemodynamic profile of nebivolol, a chemically novel, potent, and selective beta 1-adrenergic antagonist. J Cardiovasc Pharmacol. 1988 May;11(5):552-63. doi: 10.1097/00005344-198805000-00007. [Article]
Giles TD, Cockcroft JR, Pitt B, Jakate A, Wright HM: Rationale for nebivolol/valsartan combination for hypertension: review of preclinical and clinical data. J Hypertens. 2017 Sep;35(9):1758-1767. doi: 10.1097/HJH.0000000000001412. [Article]

Enzymes

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Gielen W, Cleophas TJ, Agrawal R: Nebivolol: a review of its clinical and pharmacological characteristics. Int J Clin Pharmacol Ther. 2006 Aug;44(8):344-57. [Article]
Flockhart Table of Drug Interactions [Link]
FDA Approved Drug Products: Nebivolol Tablets [Link]

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Hocht C, Bertera FM, Mayer MA, Taira CA: Issues in drug metabolism of major antihypertensive drugs: beta-blockers, calcium channel antagonists and angiotensin receptor blockers. Expert Opin Drug Metab Toxicol. 2010 Feb;6(2):199-211. doi: 10.1517/17425250903397381. [Article]

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55930.545 Da

References

Hu X, Lan T, Dai D, Xu RA, Yuan L, Zhou Q, Li Y, Cai J, Hu G: Evaluation of 24 CYP2D6 Variants on the Metabolism of Nebivolol In Vitro. Drug Metab Dispos. 2016 Nov;44(11):1828-1831. doi: 10.1124/dmd.116.071811. Epub 2016 Aug 18. [Article]

Carriers

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

FDA Approved Drug Products: Nebivolol Tablets [Link]

Drug created at October 19, 2007 21:00 / Updated at November 21, 2021 07:38

What Is Nebivolol 5 Mg Used for

Source: https://go.drugbank.com/drugs/DB04861

Murray-Prior Cabou1994

What Is Nebivolol 5 Mg Used for

Nebivolol

Targets

References

References

References

Enzymes

References

References

References

Carriers

References

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