U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H31NO4
Molecular Weight 325.443
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BISOPROLOL

SMILES

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

InChI

InChIKey=VHYCDWMUTMEGQY-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Bisoprolol is a cardioselective beta1-adrenergic blocking agent. It lower the heart rate and blood pressure and may be used to reduce workload on the heart and hence oxygen demands. This results in a reduction of heart rate, cardiac output, systolic and diastolic blood pressure, and possibly reflex orthostatic hypotension. Bisoprolol can be used to treat cardiovascular diseases such as hypertension, coronary heart disease, arrhythmias, ischemic heart diseases, and myocardial infarction after the acute event. General side effects are: fatigue, asthenia, chest pain, malaise, edema, weight gain, angioedema. Concurrent use of rifampin increases the metabolic clearance of bisoprolol fumarate, shortening its elimination half-life.

CNS Activity

Originator

Approval Year

1992
81
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
525
Substrate
525
Blocker
445
Hypertension
 8.8 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Beta-1 adrenergic receptor
Approved
7678
ZIAC
Approved (off-label)
23
PubMed

PubMed

TitleDatePubMed
Bisoprolol: a review of its use in chronic heart failure.
2002
Optimising the use of beta-blockers in older patients with heart failure.
2002
Beta-blockers work as well in women as in men.
2002 Apr 5
Beta blockers in older persons with heart failure: tolerability and impact on quality of life.
2002 Dec
Beta-blocker therapy combined with low-dose pimobendan in patients with idiopathic dilated cardiomyopathy and chronic obstructive pulmonary disease: report on two cases.
2002 May
Beta-blocker decreases the increase in QT dispersion and transmural dispersion of repolarization induced by bepridil.
2002 Nov
Influence of drugs and gender on the arterial pulse wave and natriuretic peptide secretion in untreated patients with essential hypertension.
2002 Nov
Functional beta1- and beta2-adrenoceptors in the left and right atrium of pre-hypertensive rats.
2002 Oct
[Beta blockers in heart failure. Start with low and slowly increase the dosage!].
2002 Sep 19
Storms of ventricular tachyarrhythmias associated with primary hyperparathyroidism in a patient with dilated cardiomyopathy.
2003 Jan
Patents

Patents

BE 859425
4
US 4258062
4

Sample Use Guides

In Vivo Use Guide
2.5 to 40 mg once-daily dose
Route of Administration: Oral
In Vitro Use Guide
Positive test results were obtained in the in vitro CHO Sister Chromatid Exchange (clastogenicity) test and in the mouse Lymphoma Cell (mutagenicity) assays, using concentrations of hydrochlorothiazide of 43-1300 µg/mL.
Name Type Language
BISOPROLOL
INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
BISOPROLOL [USAN]
Common Name English
BISOPROLOL [VANDF]
Common Name English
BISOPROLOL [MI]
Common Name English
2-PROPANOL, 1-(4-((2-(1-METHYLETHOXY)ETHOXY)METHYL)PHENOXY)-3-((1-METHYLETHYL)AMINO)-, (+/-)-
Systematic Name English
(+/-)-1-((.ALPHA.-(2-ISOPROPOXYETHOXY)-P-TOLYL)OXY)-3-(ISOPROPYLAMINO)-2-PROPANOL
Common Name English
EMD 33 512
Code English
BISOPROLOL [JAN]
Common Name English
BISOPROLOL [WHO-DD]
Common Name English
BISOPROLOL [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QC07BB07
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 12.4
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
LIVERTOX 111
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
WHO-ATC C09BX02
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
NDF-RT N0000175556
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 12.1
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 12.3
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
WHO-VATC QC07AB57
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
WHO-ATC C07FB07
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
NDF-RT N0000000161
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
WHO-ATC C07BB07
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
WHO-VATC QC07AB07
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
WHO-ATC C07AB07
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
WHO-ATC C07AB57
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
WHO-VATC QC07FB07
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 12.2
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
Code System Code Type Description
EVMPD
SUB13096MIG
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY
WIKIPEDIA
BISOPROLOL
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY
LactMed
66722-44-9
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY
RXCUI
19484
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY RxNorm
MESH
D017298
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY
CAS
66722-44-9
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY
PUBCHEM
2405
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY SWITZERF
DRUG BANK
DB00612
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY
INN
5225
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY
HSDB
66722-44-9
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY
IUPHAR
7129
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY
EPA CompTox
66722-44-9
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY
MERCK INDEX
M2565
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY Merck Index
NCI_THESAURUS
C61653
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY
ChEMBL
CHEMBL645
Created by admin on Tue Mar 06 10:29:56 UTC 2018 , Edited by admin on Tue Mar 06 10:29:56 UTC 2018
PRIMARY
ACTIVE MOIETY
Structure of BISOPROLOL
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966