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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

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

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

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
[The effect of aspirin on rheological properties of erythrocytes in essential hypertension].
2002
Beta-blockers work as well in women as in men.
2002 Apr 5
[Hormonal hyperactivity in heart failure. Differences in beta blockers].
2002 Aug
[Pharmacology of beta blockers and their significance for therapy of hypertension].
2002 Aug
Integrated acquisition of analytical and biopharmaceutical screening data for beta-adrenergic-drugs employing diversified macrocycle supported potentiometric detection in HPLC systems.
2002 Aug
Current research on carvedilol in heart failure.
2002 Aug
Beta blockers in older persons with heart failure: tolerability and impact on quality of life.
2002 Dec
Efficacy of domestic bisoprolol,enalapril and nifedipine retard in mild to moderate hypertension: a randomized double-blind multicenter clinical trial in China.
2002 Jul
Present and future pharmacotherapy for heart failure.
2002 Jul
[Heart failure. Only every fifth patient is properly treated?].
2002 Jun 20
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/thiazide combination for treatment of hypertensive children: a randomized double-blind, placebo-controlled trial.
2002 May
Effect of beta(1)-selective adrenergic blockade on maximal blood lactate steady state in healthy men.
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

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.
Substance Class Chemical
Created
by admin
on Tue Mar 06 10:29:56 UTC 2018
Edited
by admin
on Tue Mar 06 10:29:56 UTC 2018
Record UNII
Y41JS2NL6U
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
BINDER -> LIGAND
BINDING
TARGET -> AGONIST
Related Record Type Details
METABOLITE -> PARENT
MAJOR
PLASMA; URINE
METABOLITE -> PARENT
The AUC and elimination half-life of (S)-(-)-bisoprolol were slightly larger than those of (R)-(+)-bisoprolol. In vitro: stereoselectively of CYP2D6 (R > S) and CYP3A4 was not stereoselective.
IN-VITRO
METABOLITE -> PARENT
MINOR
PLASMA; URINE
METABOLITE -> PARENT
MINOR
PLASMA; URINE
METABOLITE -> PARENT
The AUC and elimination half-life of (S)-(-)-bisoprolol were slightly larger than those of (R)-(+)-bisoprolol. In vitro: stereoselectively of CYP2D6 (R > S) and CYP3A4 was not stereoselective.
IN-VITRO
METABOLITE -> PARENT
The AUC and elimination half-life of (S)-(-)-bisoprolol were slightly larger than those of (R)-(+)-bisoprolol. In vitro: stereoselectively of CYP2D6 (R > S) and CYP3A4 was not stereoselective.
IN-VITRO
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC