Identification

Name
Bisoprolol
Accession Number
DB00612  (APRD00257)
Type
Small Molecule
Groups
Approved
Description

Bisoprolol is a cardioselective β1-adrenergic blocking agent used for secondary prevention of myocardial infarction (MI), heart failure, angina pectoris and mild to moderate hypertension. Bisoprolol is structurally similar to metoprolol, acebutolol and atenolol in that it has two substituents in the para position of the benzene ring. The β1-selectivity of these agents is thought to be due in part to the large substituents in the para position. At lower doses (less than 20 mg daily), bisoprolol selectively blocks cardiac β1-adrenergic receptors with little activity against β2-adrenergic receptors of the lungs and vascular smooth muscle. Receptor selectivity decreases with daily doses of 20 mg or greater. Unlike propranolol and pindolol, bisoprolol does not exhibit membrane-stabilizing or sympathomimetic activity. Bisoprolol possesses a single chiral centre and is administered as a racemic mixture. Only l-bisoprolol exhibits significant β-blocking activity.

Structure
Thumb
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 297939 / EMD 33512
Product Ingredients
IngredientUNIICASInChI Key
Bisoprolol FumarateUR59KN573L104344-23-2VMDFASMUILANOL-WXXKFALUSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BisoprololTablet10 mgOralSivem Pharmaceuticals Ulc2012-06-12Not applicableCanada
BisoprololTablet5 mgOralSorres Pharma Inc2009-02-262014-06-20Canada
BisoprololTablet10 mgOralSanis Health Inc2012-10-01Not applicableCanada
BisoprololTablet5 mgOralSivem Pharmaceuticals Ulc2012-06-12Not applicableCanada
BisoprololTablet5 mgOralSanis Health Inc2012-10-01Not applicableCanada
BisoprololTablet10 mgOralSorres Pharma Inc2009-02-262014-06-20Canada
Monocor -(10mg)Tablet10 mgOralBiovail Pharmaceuticals Canada Division Of Biovail Corporation2000-06-222005-03-10Canada
Monocor -(5mg)Tablet5 mgOralBiovail Pharmaceuticals Canada Division Of Biovail Corporation2000-06-222009-07-31Canada
Sandoz BisoprololTablet5 mgOralSandoz Canada Incorporated2003-04-24Not applicableCanada
Sandoz BisoprololTablet10 mgOralSandoz Canada Incorporated2003-04-24Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-bisoprololTablet5 mgOralApotex Corporation2004-08-10Not applicableCanada
Apo-bisoprololTablet10 mgOralApotex Corporation2004-08-10Not applicableCanada
Ava-bisoprololTablet10 mgOralAvanstra Inc2011-08-222014-08-21Canada
Ava-bisoprololTablet5 mgOralAvanstra Inc2011-08-222014-08-21Canada
Bisoprolol FumarateTablet, coated5 mg/1OralAmerincan Health Packaging2011-10-042019-08-31Us
Bisoprolol FumarateTablet, film coated5 mg/1OralCitron Pharma LLC2006-12-27Not applicableUs
Bisoprolol FumarateTablet, film coated10 mg/1OralMylan Pharmaceuticals2012-09-24Not applicableUs
Bisoprolol FumarateTablet5 mg/1OralCarilion Materials Management2009-09-21Not applicableUs29300 0126 01 nlmimage10 26131378
Bisoprolol FumarateTablet5 mg/1OralRebel Distributors2009-09-21Not applicableUs
Bisoprolol FumarateTablet5 mg/1OralPreferreed Pharmaceuticals Inc.2016-10-24Not applicableUs68788 677520180913 8702 14877w9
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bisoprolol Fumarate and HydrochlorothiazideBisoprolol Fumarate (5 mg/1) + Hydrochlorothiazide (6.25 mg/1)TabletOralAidarex Pharmaceuticals LLC2010-10-12Not applicableUs
Bisoprolol Fumarate and HydrochlorothiazideBisoprolol Fumarate (5 mg/1) + Hydrochlorothiazide (6.25 mg/1)TabletOralA-S Medication Solutions2010-10-12Not applicableUs50090 078920180913 8702 cwhdeg
Bisoprolol Fumarate and HydrochlorothiazideBisoprolol Fumarate (10 mg/1) + Hydrochlorothiazide (6.25 mg/1)TabletOralNucare Pharmaceuticals, Inc.2010-10-12Not applicableUs
Bisoprolol Fumarate and HydrochlorothiazideBisoprolol Fumarate (5 mg/1) + Hydrochlorothiazide (6.25 mg/1)Tablet, coatedOralPhysicians Total Care, Inc.2002-01-15Not applicableUs00185 0704 05 nlmimage10 02048114
Bisoprolol Fumarate and HydrochlorothiazideBisoprolol Fumarate (10 mg/1) + Hydrochlorothiazide (6.25 mg/1)Tablet, coatedOralMed Pharma Co., Ltd.2011-06-102012-07-11Us
Bisoprolol Fumarate and HydrochlorothiazideBisoprolol Fumarate (2.5 mg/1) + Hydrochlorothiazide (6.25 mg/1)TabletOralUnichem Pharmaceuticals (USA), Inc.2010-10-12Not applicableUs
Bisoprolol Fumarate and HydrochlorothiazideBisoprolol Fumarate (2.5 mg/1) + Hydrochlorothiazide (6.25 mg/1)Tablet, film coatedOralMylan Pharmaceuticals2000-09-25Not applicableUs00378 0501 01 nlmimage10 ca21657b
Bisoprolol Fumarate and HydrochlorothiazideBisoprolol Fumarate (5 mg/1) + Hydrochlorothiazide (6.25 mg/1)Tablet, coatedOralRebel Distributors2000-09-25Not applicableUs
Bisoprolol Fumarate and HydrochlorothiazideBisoprolol Fumarate (2.5 mg/1) + Hydrochlorothiazide (6.25 mg/1)Tablet, coatedOralMed Pharma Co., Ltd.2011-06-102012-07-11Us
Bisoprolol Fumarate and HydrochlorothiazideBisoprolol Fumarate (5 mg/1) + Hydrochlorothiazide (6.25 mg/1)TabletOralbryant ranch prepack2010-10-12Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bisoprolol Fumarate HydrochlorothiazideBisoprolol Fumarate (2.5 mg/1) + Hydrochlorothiazide (6.25 mg/1)Tablet, film coatedOralWatson Pharmaceuticals2006-11-27Not applicableUs
Bisoprolol Fumarate HydrochlorothiazideBisoprolol Fumarate (10 mg/1) + Hydrochlorothiazide (6.25 mg/1)Tablet, film coatedOralWatson Pharmaceuticals2006-11-27Not applicableUs
Bisoprolol Fumarate HydrochlorothiazideBisoprolol Fumarate (5 mg/1) + Hydrochlorothiazide (6.25 mg/1)Tablet, film coatedOralWatson Pharmaceuticals2006-11-27Not applicableUs
International/Other Brands
Cardicor (Bayer) / Concor (Merck) / Concore (Merck) / Detensiel (Merck Santé) / Emconcor (Merck) / Emcor (Merck) / Euradal (Lacer) / Isoten (Meda) / Monocor (Biovail Pharmaceuticals) / Soprol (Helsinn)
Categories
UNII
Y41JS2NL6U
CAS number
66722-44-9
Weight
Average: 325.443
Monoisotopic: 325.225308485
Chemical Formula
C18H31NO4
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

Pharmacology

Indication

For management of heart failure, angina pectoris, and mild to moderate hypertension and for secondary prevention of myocardial infarction (MI).

Associated Conditions
Pharmacodynamics

Bisoprolol is a competitive, cardioselective β1-adrenergic antagonist. Activation of β1-receptors (located mainly in the heart) by epinephrine increases heart rate and the blood pressure causing the heart to consume more oxygen. β1-adrenergic blocking agents such as bisopolol lower the heart rate and blood pressure and may be used to reduce workload on the heart and hence oxygen demands. They are routinely prescribed in patients with ischemic heart disease. In addition, β1-selective blockers prevent the release of renin, a hormone produced by the kidneys causes constriction of blood vessels. Bisoprolol is lipophilic and exhibits no intrinsic sympathomimetic activity (ISA) or membrane-stabilizing activity.

Mechanism of action

Bisoprolol selectively blocks catecholamine stimulation of β1-adrenergic receptors in the heart and vascular smooth muscle. This results in a reduction of heart rate, cardiac output, systolic and diastolic blood pressure, and possibly reflex orthostatic hypotension. At higher doses (e.g. 20 mg and greater) bisoprolol may competitively block β2-adrenergic receptors in bronchial and vascular smooth muscle causing bronchospasm and vasodilation.

TargetActionsOrganism
ABeta-1 adrenergic receptor
antagonist
Human
NBeta-2 adrenergic receptor
antagonist
Human
Absorption

Well absorbed. Bioavailability > 80%. Absorption is not affected by food. Peak plasma concentrations occur within 2-4 hours.

Volume of distribution
Not Available
Protein binding

Binding to serum proteins is approximately 30%

Metabolism

Approximately 50% of the dose is metabolized primarily metabolized by CYP3A4 to inactive metabolites. In vitro studies have shown that bisoprolol is also metabolized by CYP2D6 though this does not appear to be clinically significant. Approximately half the administered dose is excreted in unchanged in urine.

Route of elimination

Eliminated equally by renal and non-renal pathways. Approximately 50% of the total orally administered dose is excreted unchanged in urine with the remainder appearing as inactive metabolites. Less than 2% of the dose is excreted in the feces.

Half life

9-12 hours; prolonged in the elderly and those with decreased renal function

Clearance
Not Available
Toxicity

Oral, mouse: LD50 = 100 mg/kg; Skin, rabbit: LD50 = 200 mg/kg; Skin, rat: LD50 = 500 mg/kg. Symptoms of overdose include congestive heart failure (marked by sudden weight gain, swelling of the legs, feet, and ankles, fatigue, and shortness of breath), difficult or labored breathing, low blood pressure, low blood sugar, and slow heartbeat.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Bisoprolol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Bisoprolol.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Bisoprolol.
1,10-Phenanthroline1,10-Phenanthroline may increase the bradycardic activities of Bisoprolol.
16-BromoepiandrosteroneThe metabolism of 16-Bromoepiandrosterone can be decreased when combined with Bisoprolol.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Bisoprolol is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Bisoprolol.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Bisoprolol.
4-MethoxyamphetamineThe therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Bisoprolol.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Bisoprolol.
6-Deoxyerythronolide BThe metabolism of Bisoprolol can be decreased when combined with 6-Deoxyerythronolide B.
Food Interactions
  • Take without regard to meals.

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
Not Available
External Links
Human Metabolome Database
HMDB0014750
KEGG Drug
D02342
KEGG Compound
C06852
PubChem Compound
2405
PubChem Substance
46508844
ChemSpider
2312
BindingDB
25751
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
ATC Codes
C07BB07 — Bisoprolol and thiazidesC09BX02 — Perindopril and bisoprololC07FB07 — Bisoprolol and other antihypertensivesC07AB07 — BisoprololC07AB57 — Bisoprolol, combinations
AHFS Codes
  • 24:24.00 — Beta-adrenergic Blocking Agents
MSDS
Download (73.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedDiagnosticAbdominal Aortic Aneurysm Patients Under Surveillance1
0Unknown StatusPreventionPatients With Coronary Artery Disease Scheduled for by Pass Surgery1
1CompletedBasic ScienceHealthy Volunteers / Pharmacodynamics of Mirabegron1
1CompletedTreatmentFasting1
1CompletedTreatmentFed1
1CompletedTreatmentHealthy Volunteers2
1, 2Unknown StatusTreatmentIdiopathic Pulmonary Arterial Hypertension1
2TerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Heart Failure, Unspecified1
2, 3CompletedPreventionCoronary Artery Disease / Diabetes Mellitus (DM) / Heart Failure, Unspecified1
3CompletedTreatmentChagas Cardiomyopathy / Chronic Heart Failure (CHF)1
3CompletedTreatmentHigh Blood Pressure (Hypertension)1
3RecruitingPreventionCancer, Breast / Cardiotoxicity1
4Active Not RecruitingTreatmentHypertension, Resistant to Conventional Therapy1
4CompletedHealth Services ResearchHigh Blood Pressure (Hypertension) / Metabolic Syndromes1
4CompletedPreventionAdverse Effects / Coronary Artery Atherosclerosis / Insulin resistance syndrome1
4CompletedSupportive CareHigh Blood Pressure (Hypertension)1
4CompletedTreatmentChronic Heart Failure (CHF)2
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4CompletedTreatmentCongestive Heart Failure (CHF)1
4CompletedTreatmentHeart Failure, Unspecified / Ventricular Dysfunction, Left1
4CompletedTreatmentHigh Blood Pressure (Hypertension)3
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Pharmacogenetics1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4CompletedTreatmentPostural Orthostatic Tachycardia Syndrome (POTS)1
4CompletedTreatmentUntreated Essential Hypertension1
4Not Yet RecruitingTreatmentPermanent Atrial Fibrillation1
4RecruitingTreatmentAcute Myocardial Infarction (AMI) / Non-ST Elevation Myocardial Infarction / ST Elevation Myocardial Infarction1
4RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentHeart Failure, Unspecified1
4RecruitingTreatmentHigh Blood Pressure (Hypertension)1
4RecruitingTreatmentHypertension Resistant To Conventional Therapy1
4SuspendedTreatmentHeart Rate Control in ICD Patients With Heart Failure1
4TerminatedTreatmentAortic Valve Stenosis1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableCompletedBasic ScienceArterial Hypertension / Osteopenia1
Not AvailableCompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedTreatmentClozapine-induced Sinustachycardia1
Not AvailableCompletedTreatmentMyocardial Ischemia1
Not AvailableRecruitingNot AvailableAortic Valve Stenosis / Hypertension,Essential / Impaired Renal Function / Secondary Hypertension1
Not AvailableUnknown StatusNot AvailableHeart Failure, Unspecified1
Not AvailableUnknown StatusTreatmentChronic Heart Failure (CHF)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
FormRouteStrength
TabletOral10 mg/1
TabletOral5 mg/1
Tablet, coatedOral10 mg/1
Tablet, coatedOral5 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral5 mg/1
TabletOral
Tablet, coatedOral
Tablet, film coatedOral
TabletOral10 mg
TabletOral5 mg
Prices
Unit descriptionCostUnit
Condylox 0.5% Gel 3.5 gm Tube304.93USD tube
Condylox 0.5% Solution 3.5ml Bottle143.4USD bottle
Condylox 0.5% gel97.73USD g
Zebeta 10 mg tablet3.6USD tablet
Zebeta 5 mg tablet3.6USD tablet
Bisoprolol fumarate 5 mg tablet1.78USD tablet
Bisoprolol fumarate 10 mg tablet1.24USD tablet
Bisoprolol-Hydrochlorothiazide 10-6.25 mg tablet1.19USD tablet
Bisoprolol-Hydrochlorothiazide 2.5-6.25 mg tablet1.19USD tablet
Bisoprolol-Hydrochlorothiazide 5-6.25 mg tablet1.19USD tablet
Apo-Bisoprolol 10 mg Tablet0.38USD tablet
Novo-Bisoprolol 10 mg Tablet0.38USD tablet
Pms-Bisoprolol 10 mg Tablet0.38USD tablet
Sandoz Bisoprolol 10 mg Tablet0.38USD tablet
Apo-Bisoprolol 5 mg Tablet0.23USD tablet
Novo-Bisoprolol 5 mg Tablet0.23USD tablet
Pms-Bisoprolol 5 mg Tablet0.23USD tablet
Sandoz Bisoprolol 5 mg Tablet0.23USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)100 °CPhysProp
water solubility2240 mg/LNot Available
logP1.87RECANATINI,M (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.0707 mg/mLALOGPS
logP2.3ALOGPS
logP2.2ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area59.95 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity92.15 m3·mol-1ChemAxon
Polarizability38.5 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9445
Blood Brain Barrier-0.9077
Caco-2 permeable+0.6149
P-glycoprotein substrateSubstrate0.7785
P-glycoprotein inhibitor INon-inhibitor0.807
P-glycoprotein inhibitor IINon-inhibitor0.7821
Renal organic cation transporterNon-inhibitor0.8568
CYP450 2C9 substrateNon-substrate0.8134
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateNon-substrate0.6113
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9485
CYP450 3A4 inhibitorNon-inhibitor0.8373
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9766
Ames testNon AMES toxic0.9064
CarcinogenicityNon-carcinogens0.9267
BiodegradationNot ready biodegradable0.8962
Rat acute toxicity2.0089 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7877
hERG inhibition (predictor II)Non-inhibitor0.6611
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0109000000-564ffde4ea3f59c4126f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-2903000000-5e5b905ef2026aa7f011
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00xr-9800000000-99ce6ca7b3171d63af09
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-9600000000-bfefc02f00a4439a34ba
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05fr-9500000000-4b91d206ced038eff35c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ab9-9400000000-dd6baeb57f900d719aa9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0209000000-0f37dcfed3fc1c82c470
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-5902000000-dae2a435db6b3ea664cd
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-05fr-9200000000-1cce569461a677bb6467
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0209000000-65dd49cd88f0ec134445
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00or-5709000000-360e67ed724045a9c01b

Taxonomy

Description
This compound 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
Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Dialkyl ethers / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Benzylether / Phenoxy compound / Phenol ether / Alkyl aryl ether / 1,2-aminoalcohol / Secondary alcohol / Dialkyl ether / Secondary amine / Secondary aliphatic amine / Ether
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary alcohol, secondary amine (CHEBI:3127)

Targets

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:1280737]
  2. 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. [PubMed:14757145]
  3. 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. [PubMed:16325050]
  4. 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. [PubMed:1676675]
  5. 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. [PubMed:1691366]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Antagonist
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
  1. 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. [PubMed:14757145]
  2. Bruck H, Poller U, Lussenhop H, Ponicke K, Temme T, Heusch G, Philipp T, Brodde OE: Beta 2-adrenoceptor-mediated intrinsic sympathomimetic activity of carteolol: an in vivo study. Naunyn Schmiedebergs Arch Pharmacol. 2004 Nov;370(5):361-8. Epub 2004 Oct 23. [PubMed:15526107]
  3. Motomura S, Reinhard-Zerkowski H, Daul A, Brodde OE: On the physiologic role of beta-2 adrenoceptors in the human heart: in vitro and in vivo studies. Am Heart J. 1990 Mar;119(3 Pt 1):608-19. [PubMed:1968697]
  4. Brodde OE: Bisoprolol (EMD 33512), a highly selective beta 1-adrenoceptor antagonist: in vitro and in vivo studies. J Cardiovasc Pharmacol. 1986;8 Suppl 11:S29-35. [PubMed:2439795]
  5. Daul A, Johnston T, Reher M, Kruger M, Brodde OE: Differential haemodynamic effects induced by beta 1-(bisoprolol) or beta 2-(ICI 118,551) adrenoceptor blockade in man. J Hypertens Suppl. 1986 Dec;4(6):S99-102. [PubMed:2886573]

Enzymes

Kind
Protein
Organism
Human
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
  1. Horikiri Y, Suzuki T, Mizobe M: Pharmacokinetics and metabolism of bisoprolol enantiomers in humans. J Pharm Sci. 1998 Mar;87(3):289-94. [PubMed:9523980]
  2. Horikiri Y, Suzuki T, Mizobe M: Stereoselective metabolism of bisoprolol enantiomers in dogs and humans. Life Sci. 1998;63(13):1097-108. [PubMed:9763205]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Horikiri Y, Suzuki T, Mizobe M: Pharmacokinetics and metabolism of bisoprolol enantiomers in humans. J Pharm Sci. 1998 Mar;87(3):289-94. [PubMed:9523980]
  2. Horikiri Y, Suzuki T, Mizobe M: Stereoselective metabolism of bisoprolol enantiomers in dogs and humans. Life Sci. 1998;63(13):1097-108. [PubMed:9763205]
  3. Nozawa T, Taguchi M, Tahara K, Hashimoto Y, Igarashi N, Nonomura M, Kato B, Igawa A, Inoue H: Influence of CYP2D6 genotype on metoprolol plasma concentration and beta-adrenergic inhibition during long-term treatment: a comparison with bisoprolol. J Cardiovasc Pharmacol. 2005 Nov;46(5):713-20. [PubMed:16220080]
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on September 25, 2018 17:45