Bisoprolol

Identification

Summary

Bisoprolol is a beta-1 adrenergic blocking agent used to prevent myocardial infarction and heart failure and to treat mild to moderate hypertension.

Brand Names

Ziac

Generic Name

Bisoprolol

DrugBank Accession Number

DB00612

Background

Bisoprolol is a cardioselective β1-adrenergic blocking agent used to treat high blood pressure.^4,17 It is considered a potent drug with a long-half life that can be used once daily to reduce the need for multiple doses of antihypertensive drugs.⁴ Bisoprolol is generally well tolerated, likely due to its β1-adrenergic receptor selectivity and is a useful alternative to non-selective β-blocker drugs in the treatment of hypertension such as Carvedilol and Labetalol. It may be used alone or in combination with other drugs to manage hypertension¹⁷ and can be useful in patients with chronic obstructive pulmonary disease (COPD) due to its receptor selectivity.¹³

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 325.443
Monoisotopic: 325.225308485
Chemical Formula: C₁₈H₃₁NO₄

Synonyms

(+-)-1-((alpha-(2-Isopropoxyethoxy)-p-tolyl)oxy)-3-(isopropylamino)-2-propanol
(RS)-1-(4-(2-Isopropoxyethoxymethyl)phenoxy)-3-(isopropylamino)-2-propanol
Bisoprolol
Bisoprololum

External IDs

CL 297,939
CL 297939
EMD 33 512
EMD 33512

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Pharmacology

Indication

Bisoprolol is indicated for the treatment of mild to moderate hypertension.¹⁷ It may be used off-label to treat heart failure, atrial fibrillation, and angina pectoris.^1,2

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Associated Conditions

Indication Type	Indication	Approval Level	Age Group	Dose Form
Management of	Atrial fibrillation	••• •••••
Prophylaxis of	Cardiac event	••• •••••
Management of	Heart failure	••• •••••
Used in combination to manage	High blood pressure (hypertension)	••••••••••••	•••••	••••••
Management of	High blood pressure (hypertension)	••••••••••••	•••••	••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Bisoprolol decreases heart rate (chronotropy), decreases contractility (inotropy), and reduces blood pressure.^15,17 The results of various clinical studies indicate that bisoprolol reduces cardiovascular mortality and all-cause mortality in patients with heart failure and decreased cardiac ejection fraction (EF).^3,8

Mechanism of action

Though the mechanism of action of bisoprolol has not been fully elucidated in hypertension, it is thought that therapeutic effects are achieved through the antagonism of β-1adrenoceptors to result in lower cardiac output. Bisoprolol is a competitive, cardioselective β1-adrenergic antagonist. When β1-receptors (located mainly in the heart)¹⁵ are activated by adrenergic neurotransmitters such as epinephrine, both the blood pressure and heart rate increase, leading to greater cardiovascular work, increasing the demand for oxygen. Bisoprolol reduces cardiac workload by decreasing contractility and the need for oxygen through competitive inhibition of β1-adrenergic receptors.^7,15

Bisoprolol is also thought to reduce the output of renin in the kidneys, which normally increases blood pressure. Additionally, some central nervous system effects of bisoprolol may include diminishing sympathetic nervous system output from the brain, decreasing blood pressure and heart rate.¹⁷

Target	Actions	Organism
ABeta-1 adrenergic receptor	antagonist	Humans
NBeta-2 adrenergic receptor	antagonist	Humans

Absorption

Bisoprolol is well absorbed in the gastrointestinal tract.¹⁸ The AUC is 642.87 g.hr/mL and bioavailability of bisoprolol is about 90% due to the minimal first pass effects.¹ Absorption is unaffected by food intake. Peak plasma concentrations of bisoprolol are attained within 2-4 hours and steady-state concentrations are achieved within 5 days of administration.¹⁷ In a pharmacokinetic study, the mean peak concentration of bisoprolol was 52 micrograms/L.⁶ Cmax at steady state concentrations of bisoprolol is 64±21 ng/ml administered at 10 mg daily.¹⁸

Volume of distribution

The volume of distribution of bisoprolol is 3.5 L/kg.¹⁸ The mean volume of distribution was found to be 230 L/kg in heart failure patients, which was similar to the volume of distribution in healthy patients.¹⁰ Bisoprolol is known to cross the placenta.¹⁶

Protein binding

Binding to serum proteins is approximately 30%.^9,18

Metabolism

Approximately 50% of the bisoprolol dose is eliminated by non-renal pathways. Bisoprolol is metabolized through oxidative metabolic pathways with no subsequent conjugation. Bisoprolol metabolites are polar and, therefore, really eliminated. Major metabolites found in plasma and urine are inactive. Bisoprolol is mainly metabolized by CYP3A4 (95%), whereas CYP2D6 plays a minor role. The CYP3A4-mediated metabolism of bisoprolol appears to be non-stereoselective.^14,17,23

Route of elimination

Bisoprolol is eliminated equally by both renal and hepatic pathways. About 50% of an oral dose is excreted unchanged in the urine with the remainder of the dose excreted as inactive bisoprolol metabolites. Under 2% of the ingested dose is found to be excreted in the feces.^17,18

Half-life

A pharmacokinetic study in 12 healthy individuals determined the mean plasma half-life of bisoprolol to be 10-12 hours.⁴ Another study comprised of healthy patients determined the elimination half-life to be approximately 10 hours.⁶ Renal impairment increased the half-life to 18.5 hours.⁶

Clearance

Total body clearance in healthy patients was determined to be 14.2 L/h. In patients with renal impairment, clearance was reduced to 7.8 L/h. Hepatic dysfunction also reduced the clearance of bisoprolol.⁶

Adverse Effects

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Toxicity

LD50 information Oral LD50 of bisoprolol in the mouse was 730 mg/kg.²¹

Overdose information

Signs of a β-blocker overdose include cardiovascular symptoms such as hypotension, congestive heart failure, and bradycardia. Other symptoms such as bronchospasm, and hypoglycemia may occur. If an overdose occurs with bisoprolol, supportive treatment should be initiated. Glucagon has been shown to be beneficial in bradycardia and hypotension associated with beta-blocker overdosage.¹¹ Hypoglycemia may be managed by administering IV glucose.¹⁷ Monitor the patient and administer atropine in cases of bradycardia, pressors and fluids in the case of hypotension, and conventional heart failure therapy if heart failure occurs. If heart block occurs, the patient must be closely monitored and isoproterenol infusion or transvenous cardiac pacemaker insertion should take place.¹⁷ For the management of overdose-related bronchospasm, administer bronchodilators with or without IV aminophylline. Limited research suggests that bisoprolol fumarate is not removed adequately by hemodialysis sessions.^12,17

Pathways

Pathway	Category
Bisoprolol Action Pathway	Drug action

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abacavir	Bisoprolol may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abaloparatide	The risk or severity of adverse effects can be increased when Bisoprolol is combined with Abaloparatide.
Abametapir	The serum concentration of Bisoprolol can be increased when it is combined with Abametapir.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Bisoprolol.
Abrocitinib	The serum concentration of Bisoprolol can be increased when it is combined with Abrocitinib.

Food Interactions

Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Bisoprolol fumarate	UR59KN573L	104344-23-2	VMDFASMUILANOL-WXXKFALUSA-N

Product Images

International/Other Brands

Bisocor / Cardicor (Bayer) / Concor (Merck) / Concore (Merck) / Detensiel (Merck Santé) / Emconcor (Merck) / Emcor (Merck) / Euradal (Lacer) / Isoten (Meda) / Monocor (Biovail Pharmaceuticals) / Soprol (Helsinn)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Bisoprolol	Tablet	5 mg	Oral	Sanis Health Inc	2012-10-01	Not applicable
Bisoprolol	Tablet	10 mg	Oral	Sorres Pharma Inc	2009-02-26	2014-06-20
Bisoprolol	Tablet	10 mg	Oral	Sivem Pharmaceuticals Ulc	2012-06-12	2020-07-21
Bisoprolol	Tablet	5 mg	Oral	Sorres Pharma Inc	2009-02-26	2014-06-20
Bisoprolol	Tablet	10 mg	Oral	Sanis Health Inc	2012-10-01	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ag-bisoprolol	Tablet	5 mg	Oral	Angita Pharma Inc.	2022-03-18	Not applicable
Ag-bisoprolol	Tablet	10 mg	Oral	Angita Pharma Inc.	2022-03-18	Not applicable
Apo-bisoprolol	Tablet	5 mg	Oral	Apotex Corporation	2004-08-10	Not applicable
Apo-bisoprolol	Tablet	10 mg	Oral	Apotex Corporation	2004-08-10	Not applicable
Ava-bisoprolol	Tablet	10 mg	Oral	Avanstra Inc	2011-08-22	2014-08-21

Mixture Products

Name	Ingredients	Dosage	Route	Marketing Start	Marketing End
BIRAMLO 10MG/10MG	Bisoprolol fumarate (10 mg/1) + Amlodipine besylate (10 mg/1)	Tablet	Oral	2018-10-01	Not applicable
BIRAMLO 10MG/10MG	Bisoprolol fumarate (10 mg/1) + Amlodipine besylate (10 mg/1)	Tablet	Oral	2018-10-01	Not applicable
BIRAMLO 10MG/10MG	Bisoprolol fumarate (10 mg/1) + Amlodipine besylate (10 mg/1)	Tablet	Oral	2018-10-01	Not applicable
BIRAMLO 10MG/5MG	Bisoprolol fumarate (10 mg/1) + Amlodipine besylate (5 mg/1)	Tablet	Oral	2018-10-01	Not applicable
BIRAMLO 10MG/5MG	Bisoprolol fumarate (10 mg/1) + Amlodipine besylate (5 mg/1)	Tablet	Oral	2018-10-01	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
CONCOR 10 MG 30 LAK TABLET	Bisoprolol fumarate (10 mg)	Tablet	Oral	DAİİCHİ SANKYO İLAÇ TİC. LTD. ŞTİ.	2013-01-29	Not applicable
CONCOR 5 MG 30 LAK TABLET	Bisoprolol fumarate (5 mg)	Tablet	Oral	DAİİCHİ SANKYO İLAÇ TİC. LTD. ŞTİ.	2013-01-29	Not applicable

Chemical Identifiers

UNII: Y41JS2NL6U
CAS number: 66722-44-9
InChI Key: VHYCDWMUTMEGQY-UHFFFAOYSA-N
InChI: 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
IUPAC Name: 1-[(propan-2-yl)amino]-3-(4-{[2-(propan-2-yloxy)ethoxy]methyl}phenoxy)propan-2-ol
SMILES: CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1

References

Synthesis Reference

Yoshihiro Iwao, Katsuyuki Ookubo, Katsuhiro Okada, Kunihiro Minami, Shuichiro Yuasa, "Adhesive Pharmaceutical Preparation Containing Bisoprolol." U.S. Patent US20090169604, issued July 02, 2009.

US20090169604

General References

Lancaster SG, Sorkin EM: Bisoprolol. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in hypertension and angina pectoris. Drugs. 1988 Sep;36(3):256-85. doi: 10.2165/00003495-198836030-00002. [Article]
Ishiguro H, Ikeda T, Abe A, Tsukada T, Mera H, Nakamura K, Yusu S, Yoshino H: Antiarrhythmic effect of bisoprolol, a highly selective beta1-blocker, in patients with paroxysmal atrial fibrillation. Int Heart J. 2008 May;49(3):281-93. [Article]
Metra M, Nodari S, Bordonali T, Milani P, Lombardi C, Bugatti S, Fontanella B, Verzura G, Danesi R, Dei Cas L: Bisoprolol in the treatment of chronic heart failure: from pathophysiology to clinical pharmacology and trial results. Ther Clin Risk Manag. 2007 Aug;3(4):569-78. [Article]
Leopold G, Ungethum W, Pabst J, Simane Z, Buhring KU, Wiemann H: Pharmacodynamic profile of bisoprolol, a new beta 1-selective adrenoceptor antagonist. Br J Clin Pharmacol. 1986 Sep;22(3):293-300. doi: 10.1111/j.1365-2125.1986.tb02890.x. [Article]
Nuttall SL, Routledge HC, Kendall MJ: A comparison of the beta1-selectivity of three beta1-selective beta-blockers. J Clin Pharm Ther. 2003 Jun;28(3):179-86. [Article]
Kirch W, Rose I, Demers HG, Leopold G, Pabst J, Ohnhaus EE: Pharmacokinetics of bisoprolol during repeated oral administration to healthy volunteers and patients with kidney or liver disease. Clin Pharmacokinet. 1987 Aug;13(2):110-7. doi: 10.2165/00003088-198713020-00003. [Article]
Chatterjee SS: The cardioselective and hypotensive effects of bisoprolol in hypertensive asthmatics. J Cardiovasc Pharmacol. 1986;8 Suppl 11:S74-7. [Article]
Dezsi CA, Szentes V: The Real Role of beta-Blockers in Daily Cardiovascular Therapy. Am J Cardiovasc Drugs. 2017 Oct;17(5):361-373. doi: 10.1007/s40256-017-0221-8. [Article]
Leopold G: Balanced pharmacokinetics and metabolism of bisoprolol. J Cardiovasc Pharmacol. 1986;8 Suppl 11:S16-20. [Article]
Cvan Trobec K, Grabnar I, Kerec Kos M, Vovk T, Trontelj J, Anker SD, Rosano G, Lainscak M: Bisoprolol pharmacokinetics and body composition in patients with chronic heart failure: a longitudinal study. Eur J Clin Pharmacol. 2016 Jul;72(7):813-22. doi: 10.1007/s00228-016-2041-1. Epub 2016 Mar 21. [Article]
Peterson CD, Leeder JS, Sterner S: Glucagon therapy for beta-blocker overdose. Drug Intell Clin Pharm. 1984 May;18(5):394-8. [Article]
Shroff GR, Herzog CA: beta-Blockers in dialysis patients: a nephrocardiology perspective. J Am Soc Nephrol. 2015 Apr;26(4):774-6. doi: 10.1681/ASN.2014080831. Epub 2014 Oct 30. [Article]
Albouaini K, Andron M, Alahmar A, Egred M: Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions. Int J Chron Obstruct Pulmon Dis. 2007;2(4):535-40. [Article]
Zeng W, Lao S, Guo Y, Wu Y, Huang M, Tomlinson B, Zhong G: The Influence of EGCG on the Pharmacokinetics and Pharmacodynamics of Bisoprolol and a New Method for Simultaneous Determination of EGCG and Bisoprolol in Rat Plasma. Front Nutr. 2022 May 31;9:907986. doi: 10.3389/fnut.2022.907986. eCollection 2022. [Article]
William D. Tucker; Pramod Theetha Kariyanna (2019). Selective B1 blockers. Stat Pearls Publishing.
National Collaborating Centre for Women's and Children's Health (UK) (2010). NICE Guidelines for hypertension in pregnancy. RCOG Press.
Bisoprolol monograph [Link]
Summary of product characteristics [Link]
Bisoprolol, health links AU [Link]
CaymanChem: Bisoprolol MSDS [Link]
Monograph, Bisoprolol [Link]
DailyMed Label: Bisoprolol fumarate Oral Tablets [Link]
Health Canada Approved Drug Products: BISOPROLOL (bisoprolol fumarate) tablets for oral use (January 2020) [Link]

External Links

Human Metabolome Database: HMDB0014750
KEGG Drug: D02342
KEGG Compound: C06852
PubChem Compound: 2405
PubChem Substance: 46508844
ChemSpider: 2312
BindingDB: 25751
RxNav: 19484
ChEBI: 3127
ChEMBL: CHEMBL645
Therapeutic Targets Database: DAP000483
PharmGKB: PA448641
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Bisoprolol

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Acute Myocardial Infarction (AMI) / Non ST Segment Elevation Myocardial Infarction (NSTEMI) / ST Segment Elevation Myocardial Infarction (STEMI)	1
4	Completed	Health Services Research	Hypertension / Syndrome, Metabolic	1
4	Completed	Other	Cardiac Failure / Cardiovascular Disease (CVD) / Heart Failure / Heart Failure With Preserved Ejection Fraction (HFpEF) / Heart Failure, Diastolic	2
4	Completed	Prevention	Anesthetics Adverse Reaction / Coronary Artery Atherosclerosis / Insulin resistance syndrome	1
4	Completed	Prevention	Atrial Fibrillation / Coronary Artery Bypass Grafting (CABG) / Prevention	1

Pharmacoeconomics

Manufacturers

Aurobindo pharma ltd
Mutual pharmaceutical co inc
Mylan pharmaceuticals inc
Sandoz inc
Teva pharmaceuticals usa
Unichem pharmaceuticals (usa) inc
Duramed pharmaceuticals inc sub barr laboratories inc

Packagers

Atlantic Biologicals Corporation
Aurobindo Pharma Ltd.
Duramed
Eon Labs
Greenstone LLC
Kaiser Foundation Hospital
Lake Erie Medical and Surgical Supply
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Novopharm Ltd.
Physicians Total Care Inc.
Resource Optimization and Innovation LLC
Teva Pharmaceutical Industries Ltd.
Unichem Laboratories Ltd.
Watson Pharmaceuticals
Wyeth Pharmaceuticals

Dosage Forms

Form	Route	Strength
Tablet, film coated	Oral	1.25 MG
Tablet, film coated	Oral	3.75 MG
Tablet, film coated	Oral	7.5 MG
Tablet	Oral	7.5 MG
Tablet, film coated	Oral	2.5 mg
Tablet, film coated	Oral	5 mg
Tablet	Oral	10 mg/1
Tablet	Oral	5 mg/1
Tablet, coated	Oral	10 mg/1
Tablet, coated	Oral	5 mg/1
Tablet, film coated	Oral	10 mg/1
Tablet, film coated	Oral	5 mg/1
Tablet	Oral
Tablet, coated	Oral
Tablet, film coated	Oral
Tablet, film coated	Oral
Tablet, film coated	Oral	1.06 MG
Tablet, film coated	Oral	2.50 MG
Tablet	Oral	1.25 MG
Tablet	Oral	3.75 MG
Tablet	Oral	10.000 mg
Tablet	Oral	1.250 mg
Tablet, coated	Oral	10 mg
Tablet	Oral	10 mg
Tablet	Oral	5 mg
Tablet, coated	Oral	1.25 mg
Tablet, coated	Oral	1000000 mg
Tablet, film coated	Oral	500000 mg
Tablet, film coated	Oral	10 mg
Tablet, film coated	Oral	5 mg
Tablet	Oral	5.00 mg
Tablet	Oral
Tablet, film coated	Oral	10 MG
Tablet	Oral	10 mg
Tablet	Oral	2.500 mg
Tablet	Oral	2.5 mg
Tablet	Oral	5 mg
Tablet, coated	Oral	5 mg
Tablet, coated	Oral	2.5 mg

Prices

Unit description	Cost	Unit
Condylox 0.5% Gel 3.5 gm Tube	304.93USD	tube
Condylox 0.5% Solution 3.5ml Bottle	143.4USD	bottle
Condylox 0.5% gel	97.73USD	g
Zebeta 10 mg tablet	3.6USD	tablet
Zebeta 5 mg tablet	3.6USD	tablet
Bisoprolol fumarate 5 mg tablet	1.78USD	tablet
Bisoprolol fumarate 10 mg tablet	1.24USD	tablet
Bisoprolol-Hydrochlorothiazide 10-6.25 mg tablet	1.19USD	tablet
Bisoprolol-Hydrochlorothiazide 2.5-6.25 mg tablet	1.19USD	tablet
Bisoprolol-Hydrochlorothiazide 5-6.25 mg tablet	1.19USD	tablet
Apo-Bisoprolol 10 mg Tablet	0.38USD	tablet
Novo-Bisoprolol 10 mg Tablet	0.38USD	tablet
Pms-Bisoprolol 10 mg Tablet	0.38USD	tablet
Sandoz Bisoprolol 10 mg Tablet	0.38USD	tablet
Apo-Bisoprolol 5 mg Tablet	0.23USD	tablet
Novo-Bisoprolol 5 mg Tablet	0.23USD	tablet
Pms-Bisoprolol 5 mg Tablet	0.23USD	tablet
Sandoz Bisoprolol 5 mg Tablet	0.23USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	100-103	https://www.sandoz.ca/sites/www.sandoz.ca/files/Bisoprolol_TAB_Monograph.pdf
boiling point (°C)	445.0±45.0	http://www.chemspider.com/Chemical-Structure.2312.html
logP	2.2	http://www.hmdb.ca/metabolites/HMDB0014750
logS	-3.7	http://www.hmdb.ca/metabolites/HMDB0014750
pKa	9.5	https://www.sandoz.ca/sites/www.sandoz.ca/files/Bisoprolol_TAB_Monograph.pdf

Predicted Properties

Property	Value	Source
Water Solubility	0.0707 mg/mL	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	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9445
Blood Brain Barrier	-	0.9077
Caco-2 permeable	+	0.6149
P-glycoprotein substrate	Substrate	0.7785
P-glycoprotein inhibitor I	Non-inhibitor	0.807
P-glycoprotein inhibitor II	Non-inhibitor	0.7821
Renal organic cation transporter	Non-inhibitor	0.8568
CYP450 2C9 substrate	Non-substrate	0.8134
CYP450 2D6 substrate	Substrate	0.8919
CYP450 3A4 substrate	Non-substrate	0.6113
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.923
CYP450 2C19 inhibitor	Non-inhibitor	0.9485
CYP450 3A4 inhibitor	Non-inhibitor	0.8373
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9766
Ames test	Non AMES toxic	0.9064
Carcinogenicity	Non-carcinogens	0.9267
Biodegradation	Not ready biodegradable	0.8962
Rat acute toxicity	2.0089 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7877
hERG inhibition (predictor II)	Non-inhibitor	0.6611

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-05g0-9851000000-9065ddf0b986c238395e
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-004i-0109000000-564ffde4ea3f59c4126f
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-014i-2903000000-5e5b905ef2026aa7f011
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-00xr-9800000000-99ce6ca7b3171d63af09
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-00di-9600000000-bfefc02f00a4439a34ba
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-05fr-9500000000-4b91d206ced038eff35c
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0ab9-9400000000-dd6baeb57f900d719aa9
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-004i-0209000000-0f37dcfed3fc1c82c470
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-014i-5902000000-dae2a435db6b3ea664cd
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-05fr-9200000000-1cce569461a677bb6467
MS/MS Spectrum - , positive	LC-MS/MS	splash10-004i-0209000000-65dd49cd88f0ec134445
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-00or-5709000000-360e67ed724045a9c01b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00di-1392000000-383aa58e1e42527642c5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0ir1-1960000000-06850a1e570583b89de4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-5290000000-cedb9b055fb912039e4a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00dl-6900000000-f7b17632ff5b94375c83
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052f-9200000000-2f28d2c3a5b860a640c2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-05fr-4900000000-3fa53ffaead313045f2c
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	200.3273317	predicted	DarkChem Lite v0.1.0
[M-H]-	183.86363	predicted	DeepCCS 1.0 (2019)
[M+H]+	200.0799317	predicted	DarkChem Lite v0.1.0
[M+H]+	186.22163	predicted	DeepCCS 1.0 (2019)
[M+Na]+	200.3254317	predicted	DarkChem Lite v0.1.0
[M+Na]+	192.31483	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
Kd (nM)	15	7.4	37	A15307
Ki (nM)	22.4	N/A	N/A	A15544

Details1. Beta-1 adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Receptor signaling protein activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name: ADRB1
Uniprot ID: P08588
Uniprot Name: Beta-1 adrenergic receptor
Molecular Weight: 51322.1 Da

References

Breed JG, Ciampricotti R, Tromp GP, Valster FA, Lageweg E, Van Bortel LM: Quality of life perception during antihypertensive treatment: a comparative study of bisoprolol and enalapril. J Cardiovasc Pharmacol. 1992;20(5):750-5. [Article]
Brouri F, Hanoun N, Mediani O, Saurini F, Hamon M, Vanhoutte PM, Lechat P: Blockade of beta 1- and desensitization of beta 2-adrenoceptors reduce isoprenaline-induced cardiac fibrosis. Eur J Pharmacol. 2004 Feb 6;485(1-3):227-34. [Article]
Bruck H, Leineweber K, Temme T, Weber M, Heusch G, Philipp T, Brodde OE: The Arg389Gly beta1-adrenoceptor polymorphism and catecholamine effects on plasma-renin activity. J Am Coll Cardiol. 2005 Dec 6;46(11):2111-5. Epub 2005 Nov 4. [Article]
Lipworth BJ, Irvine NA, McDevitt DG: A dose-ranging study to evaluate the beta 1-adrenoceptor selectivity of bisoprolol. Eur J Clin Pharmacol. 1991;40(2):135-9. [Article]
Mauz AB, Pelzer H: Beta-adrenoceptor-binding studies of the cardioselective beta blockers bisoprolol, H-I 42 BS, and HX-CH 44 BS to heart membranes and intact ventricular myocytes of adult rats: two beta 1-binding sites for bisoprolol. J Cardiovasc Pharmacol. 1990 Mar;15(3):421-7. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Details2. Beta-2 adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Antagonist
Curator comments: At higher doses, bisoprolol antagonizes the B2 receptors, but is normally selective for B1 receptors.

General Function: Protein homodimerization activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name: ADRB2
Uniprot ID: P07550
Uniprot Name: Beta-2 adrenergic receptor
Molecular Weight: 46458.32 Da

References

Mark G. Papich (2016). Saunders Handbook of Veterinary Drugs (4th ed.). Saunders.
Summary of product characteristics [Link]

Enzymes

Details1. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Horikiri Y, Suzuki T, Mizobe M: Pharmacokinetics and metabolism of bisoprolol enantiomers in humans. J Pharm Sci. 1998 Mar;87(3):289-94. [Article]
Zisaki A, Miskovic L, Hatzimanikatis V: Antihypertensive drugs metabolism: an update to pharmacokinetic profiles and computational approaches. Curr Pharm Des. 2015;21(6):806-22. [Article]
Bisoprolol monograph [Link]

Transporters

Details1. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Bachmakov I, Werner U, Endress B, Auge D, Fromm MF: Characterization of beta-adrenoceptor antagonists as substrates and inhibitors of the drug transporter P-glycoprotein. Fundam Clin Pharmacol. 2006 Jun;20(3):273-82. doi: 10.1111/j.1472-8206.2006.00408.x. [Article]
Tahara K, Kagawa Y, Takaai M, Taguchi M, Hashimoto Y: Directional transcellular transport of bisoprolol in P-glycoprotein-expressed LLC-GA5-COL150 cells, but not in renal epithelial LLC-PK1 Cells. Drug Metab Pharmacokinet. 2008;23(5):340-6. [Article]
Nehaj F, Sokol J, Ivankova J, Mokan M, Mokan M: Effect of Bisoprolol on the Level of Dabigatran. Am J Ther. 2018 Jul 12. doi: 10.1097/MJT.0000000000000786. [Article]
Klatt S, Fromm MF, Konig J: Transporter-mediated drug-drug interactions with oral antidiabetic drugs. Pharmaceutics. 2011 Oct 12;3(4):680-705. doi: 10.3390/pharmaceutics3040680. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Bisoprolol

Identification

Structure for Bisoprolol (DB00612)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

Enzymes

References

Transporters

References