Bisoprolol (CED0002778)

Record Information

Version

1.0

Creation Date

2016-05-25 18:21:35 UTC

Update Date

2026-08-20 01:30:43 UTC

Accession Number

CHEM022145

Identification

Common Name

Bisoprolol

Class

Small Molecule

Description

Bisoprolol is an organic compound with the chemical formula C18H31NO4 and an average molecular weight of 325.44 g/mol. Bisoprolol belongs to the benzylethers, a subclass of benzene and substituted derivatives within the organic compounds. This compound acts as an antagonist for two recorded protein targets: the Beta-1 adrenergic receptor (ADRB1) and the Beta-2 adrenergic receptor (ADRB2). It is recorded as being released from or found in nine different sources. Within the category of healthcare, pharmaceuticals, and veterinary products, it is associated with ACE inhibitors and Beta blocking agents. It has also been identified in drinking water and water supply. Additional sources include electrical and electronic equipment, specifically electrically stimulated smoking devices, as well as various household cleaning and consumer products, such as perfumes within detergents and soaps, bleaching agents, cigar cigarettes, tobacco smoke filters, and other smoking requisites. The recorded route of exposure for this compound is oral.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-1-((alpha-(2-Isopropoxyethoxy)-p-tolyl)oxy)-3-(isopropylamino)-2-propanol	ChEBI
(RS)-1-(4-(2-Isopropoxyethoxymethyl)phenoxy)-3-(isopropylamino)-2-propanol	ChEBI
Bisoprololum	ChEBI
(+-)-1-((a-(2-Isopropoxyethoxy)-p-tolyl)oxy)-3-(isopropylamino)-2-propanol	Generator
(+-)-1-((Α-(2-isopropoxyethoxy)-p-tolyl)oxy)-3-(isopropylamino)-2-propanol	Generator
Bisoprolol fumarate	HMDB
Bisoprolol fumerate	HMDB
Bisoprolol hemifumarate	HMDB
Bisoprolol fumarate (2:1) salt, (+-)-isomer	MeSH, HMDB
Bisoprolol, (-)-isomer	MeSH, HMDB
Bisoprolol, fumarate (1:1) salt	MeSH, HMDB
Merck brand OF bisoprolol fumarate	MeSH, HMDB
Bisoprolol hydrochloride	MeSH, HMDB
Bisoprolol, (+-)-isomer	MeSH, HMDB
Bisoprolol, fumarate (2:1) salt	MeSH, HMDB
Fumarate, bisoprolol	MeSH, HMDB
Bisoprolol fumarate (1:1) salt, (+-)-isomer	MeSH, HMDB
Bisoprolol methanesulfonate salt	MeSH, HMDB
Concor	MeSH, HMDB
Hydrochloride, bisoprolol	MeSH, HMDB

Chemical Formula

C₁₈H₃₁NO₄

Average Molecular Mass

325.443 g/mol

Monoisotopic Mass

325.225 g/mol

CAS Registry Number

66722-44-9

IUPAC Name

1-[(propan-2-yl)amino]-3-(4-{[2-(propan-2-yloxy)ethoxy]methyl}phenoxy)propan-2-ol

Traditional Name

1-{4-[(2-isopropoxyethoxy)methyl]phenoxy}-3-(isopropylamino)propan-2-ol

SMILES

CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1

InChI Identifier

InChI=1S/C18H31NO4/c1-14(2)19-11-17(20)13-23-18-7-5-16(6-8-18)12-21-9-10-22-15(3)4/h5-8,14-15,17,19-20H,9-13H2,1-4H3

InChI Key

VHYCDWMUTMEGQY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

Alternative Parents

Substituents

Benzylether
Phenoxy compound
Phenol ether
Alkyl aryl ether
1,2-aminoalcohol
Secondary alcohol
Dialkyl ether
Secondary amine
Secondary aliphatic amine
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:3127 )
secondary amine (CHEBI:3127 )

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	0.071 g/L	ALOGPS
logP	2.3	ALOGPS
logP	2.2	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	59.95 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	92.15 m³·mol⁻¹	ChemAxon
Polarizability	38.5 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-05g0-9851000000-9065ddf0b986c238395e	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0006-9562000000-44cee6d913e8cf6bf735	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 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
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0109000000-564ffde4ea3f59c4126f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-2903000000-5e5b905ef2026aa7f011	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00xr-9800000000-99ce6ca7b3171d63af09	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9600000000-bfefc02f00a4439a34ba	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05fr-9500000000-4b91d206ced038eff35c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ab9-9400000000-dd6baeb57f900d719aa9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0209000000-0f37dcfed3fc1c82c470	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-5902000000-dae2a435db6b3ea664cd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05fr-9200000000-1cce569461a677bb6467	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0209000000-65dd49cd88f0ec134445	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00or-5709000000-360e67ed724045a9c01b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00ls-0900000000-9da1c89fab3eea35e2eb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0109000000-0803087ee41a5f4756c4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0009000000-4d3d24ad95cf8450432d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-2903000000-a9ff8f842678e678f910	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-02vj-0902000000-601e7b32ea2f0c989a17	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001j-0900000000-215dd14dd5c87dd8442f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0109000000-0e51abd9a44743e421b7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05fr-9200000000-1462679b0a1084c8ae26	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-016r-4903000000-5783652124999b829399	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05fr-9200000000-1b822bd9354c692c1902	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0209000000-0f37dcfed3fc1c82c470	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-5902000000-dae2a435db6b3ea664cd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00or-5609000000-d86b902a70fda02119b0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ab9-9400000000-cf9b4904c1d33443252e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05fr-9500000000-4f37c79ef26472b12c04	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00xr-9800000000-371034ba58df041b4b31	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9600000000-f024197f5b89189cc848	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00b9-4297000000-cc0bff99b7a745bbca62	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00xr-7491000000-d270467937f89462ccd9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-074l-9100000000-4cf48884e326a5069985	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ab9-5389000000-210c2d248c7ee6203c45	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-7790000000-a567fd9f374a204b97ff	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9400000000-6a382f7e8c32a2d8a71c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00fr-0095000000-1b38684ac7af3550eb31	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01bd-9350000000-2b8266c899454ce714bd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ab9-9100000000-8a6c6adef3c071f6d55a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fr-2859000000-b212663722548b2223b7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fr-3900000000-0b8f6ba0cd81357948a3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-2900000000-5b5be1dade1f047b566c	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
1311.0	Log mg/kg	[740:2300]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
115	Drinking water	Drinking water & water supply	Not Available
293	Beta blocking agents	Healthcare, pharmaceuticals & veterinary products	Not Available
295	ACE inhibitors	Healthcare, pharmaceuticals & veterinary products	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
555	Bleaching Agents	Household cleaning & consumer products	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
561	Perfumes Within Detergents And Soaps	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
600	Herbicides And Algicides	Agriculture & land management	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
614	Essential Oils Or Perfumes	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
642	Footwear	Textiles, leather & furnishings	Not Available

Pathways

3 pathways

Bisoprolol Action Pathway

Bisoprolol Action Pathway (New)

Bisoprolol Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Beta-1 adrenergic receptor	B0FL73	Cavia porcellus	Predicted (SEA)	0.856341
Click to view 3D structure	Beta-1 adrenergic receptor	P18090	Rattus norvegicus	Predicted (SEA)	0.778492
Click to view 3D structure	Beta-2 adrenergic receptor	Q8K4Z4	Cavia porcellus	Predicted (SEA)	0.856341
Click to view 3D structure	Beta-1 adrenergic receptor	P08588	Humans	Predicted (SEA)	3.03612
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	29.1156
Click to view 3D structure	Beta-2 adrenergic receptor	P07550	Humans	Predicted (SEA)	5.44945
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	47.0988
Click to view 3D structure	Beta-2 adrenergic receptor	Q28044	Bos taurus	Predicted (SEA)	1.63483
Click to view 3D structure	Beta-1 adrenergic receptor	P34971	Mus musculus	Predicted (SEA)	2.10193
Click to view 3D structure	Beta-3 adrenergic receptor	P13945	Humans	Predicted (SEA)	10.7432
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	137.715
Click to view 3D structure	Beta-2 adrenergic receptor	P54833	Canis lupus familiaris	Predicted (SEA)	1.63483
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	147.602
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	106.653
Click to view 3D structure	Beta-2 adrenergic receptor	P10608	Rattus norvegicus	Predicted (SEA)	2.17978
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28564	Rattus norvegicus	Predicted (SEA)	34.0201
Click to view 3D structure	DNA (cytosine-5)-methyltransferase 1	P13864	Mus musculus	Predicted (SEA)	1.55698
Click to view 3D structure	Sigma intracellular receptor 2	Q5BJF2	Humans	Predicted (SEA)	73.4118
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	137.248
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	189.796
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	256.435
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	131.799
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	700.565
Click to view 3D structure	Beta-2 adrenergic receptor	P18762	Mus musculus	Predicted (SEA)	1.79053
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Predicted (SEA)	146.512