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
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
Molecular Formula | C18H31NO4 |
Molecular Weight | 325.443 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.healthline.com/drugs/bisoprolol/oral-tablet#Highlights1
https://www.drugs.com/ppa/bisoprolol.html
http://pharm-sci.tbzmed.ac.ir/Drug-Information/Integrative%20Medicine%20Professional%20Access/ProfDrugs/Bisoprololpd.html
http://www.drugbank.ca/drugs/DB00612
https://en.wikipedia.org/wiki/Bisoprolol
Curator's Comment: description was created based on several sources, including:
http://www.healthline.com/drugs/bisoprolol/oral-tablet#Highlights1
https://www.drugs.com/ppa/bisoprolol.html
http://pharm-sci.tbzmed.ac.ir/Drug-Information/Integrative%20Medicine%20Professional%20Access/ProfDrugs/Bisoprololpd.html
http://www.drugbank.ca/drugs/DB00612
https://en.wikipedia.org/wiki/Bisoprolol
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL213 |
8.8 nM [IC50] | ||
Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9523980 |
|||
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9523980 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZIAC Approved UseBISOPROLOL FUMARATE is indicated in the management of hypertension. It may be used alone or in combination with other antihypertensive agents. Launch Date1993 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
52 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2887325/ |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BISOPROLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
40.37 ng/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BISOPROLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
661 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2887325/ |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BISOPROLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
609.8 ng × h/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BISOPROLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2887325/ |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BISOPROLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
11.07 h |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BISOPROLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
70% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2887325/ |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BISOPROLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
70% |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BISOPROLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
10 mg single, oral |
unhealthy, 37 - 52 years Health Status: unhealthy Age Group: 37 - 52 years Sex: M+F Sources: |
Other AEs: Dizziness, Tiredness... Other AEs: Dizziness (2 patients) Sources: Tiredness (1 patient) Shortness of breath (1 patient) Faintness (1 patient) |
10 mg 1 times / day steady, oral Highest studied dose Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
|
5 mg 1 times / day steady, intravenous Highest studied dose Dose: 5 mg, 1 times / day Route: intravenous Route: steady Dose: 5 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
|
20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Disc. AE: Bradycardia, Fatigue... AEs leading to discontinuation/dose reduction: Bradycardia (< 1%) Sources: Fatigue (< 1%) |
20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Other AEs: Sweating increased, Arthralgia... Other AEs: Sweating increased (0.7%) Sources: Arthralgia (2.2%) Dizziness (2.9%) Headache (8.8%) Hypoaesthesia (1.1%) Dry mouth (0.7%) Bradycardia (0.4%) Insomnia (1.5%) Diarrhea (2.6%) Nausea (1.5%) Vomiting (1.1%) |
40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Disc. AE: Bradycardia, Fatigue... AEs leading to discontinuation/dose reduction: Bradycardia (< 1%) Sources: Fatigue (< 1%) |
40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Other AEs: Sweating increased, Arthralgia... Other AEs: Sweating increased (1%) Sources: Arthralgia (2.7%) Dizziness (3.5%) Headache (10.9%) Hypoaesthesia (1.5%) Dry mouth (1.3%) Bradycardia (0.5%) Insomnia (2.5%) Depression (0.2%) Diarrhea (3.5%) Nausea (2.2%) Vomiting (1.5%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Faintness | 1 patient | 10 mg single, oral |
unhealthy, 37 - 52 years Health Status: unhealthy Age Group: 37 - 52 years Sex: M+F Sources: |
Shortness of breath | 1 patient | 10 mg single, oral |
unhealthy, 37 - 52 years Health Status: unhealthy Age Group: 37 - 52 years Sex: M+F Sources: |
Tiredness | 1 patient | 10 mg single, oral |
unhealthy, 37 - 52 years Health Status: unhealthy Age Group: 37 - 52 years Sex: M+F Sources: |
Dizziness | 2 patients | 10 mg single, oral |
unhealthy, 37 - 52 years Health Status: unhealthy Age Group: 37 - 52 years Sex: M+F Sources: |
Bradycardia | < 1% Disc. AE |
20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Fatigue | < 1% Disc. AE |
20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Bradycardia | 0.4% | 20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Dry mouth | 0.7% | 20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Sweating increased | 0.7% | 20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Hypoaesthesia | 1.1% | 20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Vomiting | 1.1% | 20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Insomnia | 1.5% | 20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Nausea | 1.5% | 20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Arthralgia | 2.2% | 20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Diarrhea | 2.6% | 20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Dizziness | 2.9% | 20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Headache | 8.8% | 20 mg 1 times / day steady, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Bradycardia | < 1% Disc. AE |
40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Fatigue | < 1% Disc. AE |
40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Depression | 0.2% | 40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Bradycardia | 0.5% | 40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Sweating increased | 1% | 40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Dry mouth | 1.3% | 40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Hypoaesthesia | 1.5% | 40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Vomiting | 1.5% | 40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Headache | 10.9% | 40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Nausea | 2.2% | 40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Insomnia | 2.5% | 40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Arthralgia | 2.7% | 40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Diarrhea | 3.5% | 40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Dizziness | 3.5% | 40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Carvedilol versus other beta-blockers in heart failure. | 2001 May |
|
[Cost-effectiveness of bisoprolol in chronic heart failure]. | 2002 Feb 14 |
|
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
Substance Class |
Chemical
Created
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Record UNII |
Y41JS2NL6U
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Validated (UNII)
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WHO-VATC |
QC07BB07
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NCI_THESAURUS |
C29576
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WHO-ESSENTIAL MEDICINES LIST |
12.4
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LIVERTOX |
NBK548471
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WHO-ATC |
C09BX02
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NDF-RT |
N0000175556
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WHO-ESSENTIAL MEDICINES LIST |
12.1
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WHO-ESSENTIAL MEDICINES LIST |
12.3
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WHO-VATC |
QC07AB57
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WHO-ATC |
C07FB07
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WHO-ATC |
C07FX04
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NDF-RT |
N0000000161
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WHO-ATC |
C07BB07
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WHO-VATC |
QC07AB07
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WHO-ATC |
C07AB07
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WHO-ATC |
C07AB57
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WHO-VATC |
QC07FB07
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WHO-ESSENTIAL MEDICINES LIST |
12.2
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100000092277
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SUB13096MIG
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Y41JS2NL6U
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Y41JS2NL6U
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3127
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Y-69
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BISOPROLOL
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19484
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D017298
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66722-44-9
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Bisoprolol
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2405
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DB00612
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5225
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8316
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7129
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DTXSID6022682
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m2565
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C61653
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CHEMBL645
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380
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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TARGET -> AGONIST | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
PLASMA; URINE
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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
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METABOLITE -> PARENT |
MINOR
PLASMA; URINE
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METABOLITE -> PARENT |
MINOR
PLASMA; URINE
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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
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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
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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