Nebivolol (CED0004167)

Record Information

Version

1.0

Creation Date

2016-05-25 18:28:48 UTC

Update Date

2026-08-21 22:19:20 UTC

Accession Number

CHEM022339

Identification

Common Name

Nebivolol

Class

Small Molecule

Description

Nebivolol is an organic compound with the chemical formula C22H25F2NO4 and an average molecular weight of 405.44 g/mol. Nebivolol belongs to the 1-benzopyrans, a subclass of benzopyrans within the organic compounds. It is categorized under the superclass of organoheterocyclic compounds. This compound has been identified in five recorded sources, including household cleaning and consumer products such as non electric simulated smoking devices, as well as healthcare, pharmaceuticals and veterinary products including lipid modifying agents, ACE inhibitors, Beta blocking agents, and Angiotensin ii receptor blockers (arbs). The recorded route of exposure for this substance is oral. In terms of biological activity, nebivolol interacts with three recorded protein targets, acting as an agonist or antagonist of the Beta-1 adrenergic receptor (ADRB1), Beta-2 adrenergic receptor (ADRB2), and Beta-3 adrenergic receptor (ADRB3).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,1'-[Bis(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)]-2,2'-iminodiethanol	ChEBI
1,1'-Bis(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2,2'-iminodiethanol	ChEBI
alpha,Alpha'-(iminobismethylene)bis-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol)	ChEBI
a,Alpha'-(iminobismethylene)bis-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol)	Generator
Α,alpha'-(iminobismethylene)bis-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol)	Generator
Lobivon	MeSH, HMDB
Nebilet	MeSH, HMDB
Bystolic	MeSH, HMDB
Silostar	MeSH, HMDB
alpha,Alpha'-(iminobis(methylene))bis(6-fluoro-3,4-dihydro)-2H-1-benzopyran-2-methanol	MeSH, HMDB
Nebivolol hydrochloride	MeSH, HMDB
Hydrochloride, nebivolol	MeSH, HMDB

Chemical Formula

C₂₂H₂₅F₂NO₄

Average Molecular Mass

405.435 g/mol

Monoisotopic Mass

405.175 g/mol

CAS Registry Number

99200-09-6

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

Traditional Name

nebivolol

SMILES

OC(CNCC(O)C1CCC2=C(O1)C=CC(F)=C2)C1CCC2=C(O1)C=CC(F)=C2

InChI Identifier

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

InChI Key

KOHIRBRYDXPAMZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

1-benzopyran
Alkyl aryl ether
Aralkylamine
Aryl fluoride
Aryl halide
Benzenoid
1,2-aminoalcohol
Secondary alcohol
Oxacycle
Secondary amine
Secondary aliphatic amine
Ether
Hydrocarbon derivative
Organofluoride
Organohalogen compound
Organonitrogen compound
Organooxygen compound
Alcohol
Organic oxygen compound
Amine
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:64019 )
secondary alcohol (CHEBI:64019 )
secondary amino compound (CHEBI:64019 )
diol (CHEBI:64019 )
chromanes (CHEBI:64019 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.04 g/L	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0fl0-5961000000-db2c9843ee0cc7cd22d4	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0uyi-5938020000-00d8599d082d3d916116	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0422900000-3a76b3b1c885bee2c157	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0920000000-11009825045a0e91f879	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002f-7900000000-89e04031c6d9dd83e8d9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0110900000-47f58423e59e787b770f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0w29-0981500000-2d7231867b467c291df3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0901000000-d5b818ab1077956bf711	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052r-0019500000-56ad16915cb134a20326	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f79-0983100000-6b2434dec2b7d46416b3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zmi-2951000000-26ef603038764485eb8e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0001900000-0ee3540a0db5557266e4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-2782900000-779d8fdfb894ef489226	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0unj-0911000000-7a81d0684fb81815d37c	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
810.0	Log mg/kg	[460:1400]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
293	Beta blocking agents	Healthcare, pharmaceuticals & veterinary products	Not Available
295	ACE inhibitors	Healthcare, pharmaceuticals & veterinary products	Not Available
296	Angiotensin ii receptor blockers (arbs)	Healthcare, pharmaceuticals & veterinary products	Not Available
298	Lipid modifying agents	Healthcare, pharmaceuticals & veterinary products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available

Pathways

4 pathways

Nebivolol Action Pathway

Nebivolol Action Pathway (New)

Nebivolol Drug Metabolism Action Pathway

Nebivolol Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Leucine--tRNA ligase, cytoplasmic	P26637	Saccharomyces cerevisiae S288c	Predicted (SEA)	1.01204
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	1131.07
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	1146.95
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	833.22
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	1034.15
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	986.739
Click to view 3D structure	Vacuolar protein sorting-associated protein 4B	O75351	Humans	Predicted (SEA)	3.73676
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	1666.83
Click to view 3D structure	Sodium/calcium exchanger 1	P32418	Humans	Predicted (SEA)	15.0249
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	2332.6
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P14842	Rattus norvegicus	Predicted (SEA)	1090.2
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	1779.09
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	2223.61
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	2974.31
Click to view 3D structure	Norepinephrine transporter	Q9WTR4	Rattus norvegicus	Predicted (SEA)	435.255
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	3354.68
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	2276.7
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	5784.59
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	919.477
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	1410.86
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	1790.3
Click to view 3D structure	D(1B) dopamine receptor	P21918	Humans	Predicted (SEA)	1548.65
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	2387.4
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	467.874
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	3217.04