Identification

Name
Atenolol
Accession Number
DB00335  (APRD00172)
Type
Small Molecule
Groups
Approved
Description

A cardioselective beta-adrenergic blocker possessing properties and potency similar to propranolol, but without a negative inotropic effect.

Structure
Thumb
Synonyms
  • 1-p-Carbamoylmethylphenoxy-3-isopropylamino-2-propanol
  • 2-(p-(2-Hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide
  • 4-(2-Hydroxy-3-((1-methylethyl)amino)propoxy)benzeneacetamide
  • Atenololum
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act AtenololTablet50 mgOralActavis Pharma Company2004-08-13Not applicableCanada
Act AtenololTablet100 mgOralActavis Pharma Company2004-08-13Not applicableCanada
AtenololTablet100 mgOralSivem Pharmaceuticals Ulc1999-03-09Not applicableCanada
AtenololTablet100 mgOralIvax Pharmaceuticals IncorporatedNot applicableNot applicableCanada
AtenololTablet50 mgOralMeliapharm Inc2011-04-082014-06-25Canada
AtenololTablet100 mgOralSanis Health Inc2017-10-20Not applicableCanada
AtenololTablet50 mgOralSivem Pharmaceuticals Ulc1999-09-03Not applicableCanada
AtenololTablet50 mgOralPro Doc Limitee1989-12-31Not applicableCanada
AtenololTablet50 mgOralIvax Pharmaceuticals IncorporatedNot applicableNot applicableCanada
AtenololTablet25 mgOralSivem Pharmaceuticals Ulc2003-04-21Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ag-atenololTablet100 mgOralAngita Pharma Inc.Not applicableNot applicableCanada
Ag-atenololTablet50 mgOralAngita Pharma Inc.Not applicableNot applicableCanada
Ag-atenololTablet25 mgOralAngita Pharma Inc.Not applicableNot applicableCanada
Apo-atenol Tab 100mgTablet100 mgOralApotex Corporation1988-12-31Not applicableCanada
Apo-atenol Tab 50mgTablet50 mgOralApotex Corporation1988-12-31Not applicableCanada
AtenololTablet100 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
AtenololTablet100 mg/1OralPd Rx Pharmaceuticals, Inc.1991-09-172018-01-12Us
AtenololTablet50 mg/1OralApotheca, Inc.2007-12-04Not applicableUs
AtenololTablet100 mg/1OralNucare Pharmaceuticals,inc.1995-02-17Not applicableUs
AtenololTablet100 mg/1OralUnit Dose Services1991-09-17Not applicableUs70786 150720180907 15195 wvnz7r
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Apo-atenidoneAtenolol (100 mg) + Chlorthalidone (25 mg)TabletOralApotex Corporation2004-08-12Not applicableCanada
Apo-atenidoneAtenolol (50 mg) + Chlorthalidone (25 mg)TabletOralApotex Corporation2004-08-12Not applicableCanada
Atenolol and ChlorthalidoneAtenolol (50 mg/1) + Chlorthalidone (25 mg/1)TabletOralClinical Solutions Wholsesale1992-08-012017-06-15Us58118 010320180913 8702 1alup5k
Atenolol and ChlorthalidoneAtenolol (100 mg/1) + Chlorthalidone (25 mg/1)TabletOralbryant ranch prepack1992-08-01Not applicableUs
Atenolol and ChlorthalidoneAtenolol (50 mg/1) + Chlorthalidone (25 mg/1)TabletOralActavis Pharma Company1992-08-01Not applicableUs0591 578220180907 15195 ndkyl9
Atenolol and ChlorthalidoneAtenolol (50 mg/1) + Chlorthalidone (25 mg/1)TabletOralMylan Pharmaceuticals1993-10-312020-04-30Us0378 206320180913 8702 rfj0yw
Atenolol and ChlorthalidoneAtenolol (100 mg/1) + Chlorthalidone (25 mg/1)TabletOralRebel Distributors1992-08-01Not applicableUs
Atenolol and ChlorthalidoneAtenolol (100 mg/1) + Chlorthalidone (25 mg/1)TabletOralLake Erie Medical Dba Quality Care Produts Llc2013-03-282015-12-31Us
Atenolol and ChlorthalidoneAtenolol (100 mg/1) + Chlorthalidone (25 mg/1)TabletOralLake Erie Medical Dba Quality Care Produts Llc1992-08-012016-06-01Us
Atenolol and ChlorthalidoneAtenolol (50 mg/1) + Chlorthalidone (25 mg/1)TabletOralPhysicians Total Care, Inc.1995-05-02Not applicableUs54868 268320180906 25352 ay2059
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AtenololAtenolol (50 mg/1)TabletOralWatson Pharmaceuticals2007-03-02Not applicableUs
AtenololAtenolol (25 mg/1)TabletOralCaraco Pharmaceutical Laboratories, Ltd.2007-07-10Not applicableUs
AtenololAtenolol (100 mg/1)TabletOralCaraco Pharmaceutical Laboratories, Ltd.2007-07-10Not applicableUs
AtenololAtenolol (100 mg/1)TabletOralWatson Pharmaceuticals2007-03-02Not applicableUs
AtenololAtenolol (50 mg/1)TabletOralCaraco Pharmaceutical Laboratories, Ltd.2007-07-10Not applicableUs
Atenolol ScopolamineAtenolol (25 mg/25.25mg) + Scopolamine (.25 mg/25.25mg)TabletBuccal; Oral; Sublingual; TransmucosalTPS2014-10-01Not applicableUs
Atenolol ScopolamineAtenolol (50 mg/50.5mg) + Scopolamine (.5 mg/50.5mg)TabletOralTPS2014-10-01Not applicableUs
International/Other Brands
Myocord (Ivax) / Normiten (Teva)
Categories
UNII
50VV3VW0TI
CAS number
29122-68-7
Weight
Average: 266.3361
Monoisotopic: 266.16304258
Chemical Formula
C14H22N2O3
InChI Key
METKIMKYRPQLGS-UHFFFAOYSA-N
InChI
InChI=1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)
IUPAC Name
2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide
SMILES
CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1

Pharmacology

Indication

For the management of hypertention and long-term management of patients with angina pectoris

Associated Conditions
Pharmacodynamics

Atenolol, a competitive beta(1)-selective adrenergic antagonist, has the lowest lipid solubility of this drug class. Although it is similar to metoprolol, atenolol differs from pindolol and propranolol in that it does not have intrinsic sympathomimetic properties or membrane-stabilizing activity. Atenolol is used alone or with chlorthalidone in the management of hypertension and edema.

Mechanism of action

Like metoprolol, atenolol competes with sympathomimetic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart and vascular smooth muscle, inhibiting sympathetic stimulation. This results in a reduction in resting heart rate, cardiac output, systolic and diastolic blood pressure, and reflex orthostatic hypotension. Higher doses of atenolol also competitively block beta(2)-adrenergic responses in the bronchial and vascular smooth muscles.

TargetActionsOrganism
ABeta-1 adrenergic receptor
antagonist
Human
UBeta-2 adrenergic receptor
inhibitor
Human
Absorption

Approximately 50% of an oral dose is absorbed from the gastrointestinal tract, the remainder being excreted unchanged in the feces.

Volume of distribution
Not Available
Protein binding

Plasma protein binding is 6-16%

Metabolism

Hepatic (minimal)

Route of elimination

Approximately 50% of an oral dose is absorbed from the gastrointestinal tract, the remainder being excreted unchanged in the feces. Unlike propranolol or metoprolol, but like nadolol, atenolol undergoes little or no metabolism by the liver, and the absorbed portion is eliminated primarily by renal excretion.

Half life

6-7 hours

Clearance
Not Available
Toxicity

LD50=2000-3000 mg/kg(orally in mice). Symptoms of an atenolol overdose include a slow heart beat, shortness of breath, fainting, dizziness, weakness, confusion, nausea, and vomiting.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Atenolol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Beta-1 adrenergic receptor---(C;C) / (C;G)G > CEffect Directly StudiedPatients with this genotype have a greater reduction in blood pressure with atenolol.Details

Interactions

Drug Interactions
DrugInteraction
1,10-Phenanthroline1,10-Phenanthroline may increase the bradycardic activities of Atenolol.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Atenolol is combined with 3-isobutyl-1-methyl-7H-xanthine.
4-MethoxyamphetamineThe therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Atenolol.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when Atenolol is combined with 6-O-benzylguanine.
7-DeazaguanineThe risk or severity of adverse effects can be increased when Atenolol is combined with 7-Deazaguanine.
7,9-DimethylguanineThe risk or severity of adverse effects can be increased when Atenolol is combined with 7,9-Dimethylguanine.
8-azaguanineThe risk or severity of adverse effects can be increased when Atenolol is combined with 8-azaguanine.
8-chlorotheophyllineThe risk or severity of adverse effects can be increased when Atenolol is combined with 8-chlorotheophylline.
9-DeazaguanineThe risk or severity of adverse effects can be increased when Atenolol is combined with 9-Deazaguanine.
9-MethylguanineThe risk or severity of adverse effects can be increased when Atenolol is combined with 9-Methylguanine.
Food Interactions
  • Consult your doctor before taking large amounts of Vitamin K (Green leafy vegetables).
  • Take 30-60 minutes before meals, take at the same time each day.

References

Synthesis Reference

Barrett, A.M., Carter, J., Hull, R., Le Count, D.J. and Squire, C.J.; U.S. Patent 3,663,607; May 16, 1972; assigned to Imperial Chemical Industries Limited, England. Barrett, A.M., Carter, J., Hull, R., Le Count, D.J. and Squire, C.J.; U.S. Patent 3,836,671; September 17, 1974; assigned to Imperial Chemical Industries Limited, England.

US3663607
General References
Not Available
External Links
Human Metabolome Database
HMDB0001924
KEGG Drug
D00235
PubChem Compound
2249
PubChem Substance
46506915
ChemSpider
2162
BindingDB
25753
ChEBI
2904
ChEMBL
CHEMBL24
Therapeutic Targets Database
DAP000482
PharmGKB
PA448499
IUPHAR
548
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Atenolol
ATC Codes
C07CB03 — Atenolol and other diureticsC07FB03 — Atenolol and other antihypertensivesC07DB01 — Atenolol, thiazides and other diureticsC07BB03 — Atenolol and thiazidesC07CB53 — Atenolol and other diuretics, combinationsC07AB03 — Atenolol
AHFS Codes
  • 24:24.00 — Beta-adrenergic Blocking Agents
FDA label
Download (112 KB)
MSDS
Download (72.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingBasic ScienceBone, Age-related / Osteoporosis, Age-Related1
0Not Yet RecruitingTreatmentBlood Pressures / High Blood Pressure (Hypertension)1
0RecruitingPreventionChronic Hypertension Complicating Pregnancy (Diagnosis) / Preeclampsia1
0RecruitingPreventionObesity, Morbid / Preeclampsia1
1CompletedBasic ScienceN/A - Healthy Subjects1
1CompletedTreatmentAnginal Pain / High Blood Pressure (Hypertension)1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHigh Blood Pressure (Hypertension)2
1TerminatedOtherHealthy Volunteers1
1, 2TerminatedTreatmentOrthostatic Intolerance / Postural Orthostatic Tachycardia Syndrome (POTS)1
2CompletedTreatmentHigh Blood Pressure (Hypertension)2
2CompletedTreatmentMarfan Syndrome1
2Not Yet RecruitingTreatmentMigraine Disorders / Vestibular Diseases / Vestibular Migraine1
2RecruitingPreventionStress Disorders, Post-Traumatic1
2RecruitingTreatmentAngina Pectoris1
2, 3CompletedTreatmentHigh Blood Pressure (Hypertension)1
3CompletedPreventionCardiac Diseases1
3CompletedPreventionCardiovascular Disease (CVD) / Cerebrovascular Disorders / Heart Diseases / High Blood Pressure (Hypertension)1
3CompletedTreatmentAtherosclerotic Cardiovascular Diseases / Hypertension,Essential1
3CompletedTreatmentCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Ischemia1
3CompletedTreatmentCardiovascular Disease (CVD) / Heart Diseases / High Blood Pressure (Hypertension) / Vascular Diseases1
3CompletedTreatmentHigh Blood Pressure (Hypertension)2
3CompletedTreatmentLeft Ventricular Hypertrophy1
3CompletedTreatmentMarfan Syndrome3
3CompletedTreatmentMitral Valve Stenosis1
3RecruitingTreatmentCerebral Small Vessels Disease1
3RecruitingTreatmentHemangiomas1
3RecruitingTreatmentInfantile Hemangiomas1
3TerminatedTreatmentHeart Failure, Unspecified / Nonvalvular Atrial Fibrillation1
3TerminatedTreatmentHemodialysis-dependent patients / High Blood Pressure (Hypertension) / Left Ventricular Hypertrophy1
3Unknown StatusPreventionMarfan Syndrome1
3Unknown StatusTreatmentCardiovascular Disease (CVD)1
4Active Not RecruitingTreatmentBlood Pressures / Stroke, Ischemic1
4CompletedHealth Services ResearchHigh Blood Pressure (Hypertension) / Metabolic Syndromes1
4CompletedPreventionNonvalvular Atrial Fibrillation1
4CompletedPreventionPerioperative Hypertension1
4CompletedSupportive CareBlood Pressures / Exercise1
4CompletedTreatmentAtherosclerosis / Endothelial Function1
4CompletedTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Hypertension,Essential / Strokes1
4CompletedTreatmentChronic Stable Angina Pectoris1
4CompletedTreatmentCoronary Artery Disease / High Blood Pressure (Hypertension)1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHigh Blood Pressure (Hypertension)11
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Insulin Resistance / Metabolic Syndromes1
4CompletedTreatmentMarfan Syndrome1
4CompletedTreatmentPost Operative Cognitive Dysfunction1
4CompletedTreatmentUntreated Essential Hypertension1
4TerminatedTreatmentCarotid Plaques / Hypertension,Essential1
4TerminatedTreatmentType 2 Diabetes Mellitus1
4Unknown StatusPreventionDiabetic Nephropathies1
4Unknown StatusTreatmentBlood Pressures1
4Unknown StatusTreatmentChronic Stable Angina Pectoris1
4Unknown StatusTreatmentGeneral Surgery1
4Unknown StatusTreatmentSmall Abdominal Aortic Aneurysm1
4WithdrawnTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableActive Not RecruitingTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension)1
Not AvailableCompletedOtherHealthy Volunteers1
Not AvailableCompletedPreventionAtherosclerosis / Cardiovascular Disease (CVD) / Cerebral Arteriosclerosis / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / Heart Diseases / High Blood Pressure (Hypertension)1
Not AvailableCompletedPreventionCardiovascular Disease (CVD)1
Not AvailableCompletedSupportive CareOrthognathic Surgery1
Not AvailableCompletedTreatmentArrythmias / Nonvalvular Atrial Fibrillation1
Not AvailableCompletedTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableCompletedTreatmentNonvalvular Atrial Fibrillation1
Not AvailableTerminatedTreatmentCachexia / Cancer, Advanced1
Not AvailableUnknown StatusBasic ScienceHealthy Volunteers1

Pharmacoeconomics

Manufacturers
  • Astrazeneca pharmaceuticals lp
  • Able laboratories inc
  • Apothecon sub bristol myers squibb co
  • Aurobindo pharma ltd
  • Caraco pharmaceutical laboratories ltd
  • Dava pharmaceuticals inc
  • Genpharm pharmaceuticals inc
  • Ipca laboratories ltd
  • Ipr pharmaceuticals inc
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Northstar healthcare holdings ltd
  • Nostrum laboratories inc
  • Pliva inc
  • Sandoz inc
  • Scs pharmaceuticals
  • Teva pharmaceuticals usa inc
  • Teva pharmaceuticals usa
  • Unique pharmaceutical laboratories
  • Watson laboratories inc
  • Zydus pharmaceuticals usa inc
  • Astrazeneca lp
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • AstraZeneca Inc.
  • Aurobindo Pharma Ltd.
  • Bryant Ranch Prepack
  • Cadila Healthcare Ltd.
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Darby Dental Supply Co. Inc.
  • DAVA Pharmaceuticals
  • Dept Health Central Pharmacy
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Genpharm LP
  • Golden State Medical Supply Inc.
  • Group Health Cooperative
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Innovative Manufacturing and Distribution Services Inc.
  • Ipca Laboratories Ltd.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Mallinckrodt Inc.
  • Medisca Inc.
  • Medvantx Inc.
  • Merckle GmbH
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mutual Pharmaceutical Co.
  • Mylan
  • Neighborcare Repackaging Inc.
  • Northstar Rx LLC
  • Norwich Pharmaceuticals Inc.
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • Pack Pharmaceuticals
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Piramal Healthcare
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Qualitest
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Remedy Repack
  • Sandhills Packaging Inc.
  • Sandoz
  • Southwood Pharmaceuticals
  • Stat Scripts LLC
  • Talbert Medical Management Corp.
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Va Cmop Dallas
  • Vangard Labs Inc.
  • Watson Pharmaceuticals
  • Zydus Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral100 mg/1
TabletOral25 mg/1
TabletOral50 mg/1
TabletOral50 mg/1mg
TabletBuccal; Oral; Sublingual; Transmucosal
TabletOral25 mg
TabletOral
Injection, solutionIntravenous5 mg/10mL
TabletOral100 mg
TabletOral50 mg
Prices
Unit descriptionCostUnit
Atenolol powder5.14USD g
Tenormin 100 mg tablet2.28USD tablet
Tenormin 25 mg tablet1.94USD tablet
Tenormin 50 mg tablet1.52USD tablet
Atenolol 100 mg tablet1.26USD tablet
Atenolol 50 mg tablet0.85USD tablet
Atenolol 25 mg tablet0.81USD tablet
Apo-Atenol 100 mg Tablet0.6USD tablet
Co Atenolol 100 mg Tablet0.6USD tablet
Mylan-Atenolol 100 mg Tablet0.6USD tablet
Novo-Atenol 100 mg Tablet0.6USD tablet
Phl-Atenolol 100 mg Tablet0.6USD tablet
Pms-Atenolol 100 mg Tablet0.6USD tablet
Ran-Atenolol 100 mg Tablet0.6USD tablet
Ratio-Atenolol 100 mg Tablet0.6USD tablet
Sandoz Atenolol 100 mg Tablet0.6USD tablet
Apo-Atenol 50 mg Tablet0.36USD tablet
Co Atenolol 50 mg Tablet0.36USD tablet
Mylan-Atenolol 50 mg Tablet0.36USD tablet
Novo-Atenol 50 mg Tablet0.36USD tablet
Phl-Atenolol 50 mg Tablet0.36USD tablet
Pms-Atenolol 50 mg Tablet0.36USD tablet
Ran-Atenolol 50 mg Tablet0.36USD tablet
Ratio-Atenolol 50 mg Tablet0.36USD tablet
Sandoz Atenolol 50 mg Tablet0.36USD tablet
Novo-Atenol 25 mg Tablet0.18USD tablet
Pms-Atenolol 25 mg Tablet0.18USD 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)158-160Barrett, A.M., Carter, J., Hull, R., Le Count, D.J. and Squire, C.J.; U.S. Patent 3,663,607; May 16, 1972; assigned to Imperial Chemical Industries Limited, England. Barrett, A.M., Carter, J., Hull, R., Le Count, D.J. and Squire, C.J.; U.S. Patent 3,836,671; September 17, 1974; assigned to Imperial Chemical Industries Limited, England.
water solubility1.33E+004 mg/L (at 25 °C)MCFARLAND,JW ET AL. (2001)
logP0.16HANSCH,C ET AL. (1995)
Caco2 permeability-6.44ADME Research, USCD
pKa9.6MERCK INDEX (2001)
Predicted Properties
PropertyValueSource
Water Solubility0.429 mg/mLALOGPS
logP0.57ALOGPS
logP0.43ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)14.08ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area84.58 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.51 m3·mol-1ChemAxon
Polarizability29.98 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9831
Blood Brain Barrier-0.9505
Caco-2 permeable-0.7922
P-glycoprotein substrateSubstrate0.6773
P-glycoprotein inhibitor INon-inhibitor0.9446
P-glycoprotein inhibitor IINon-inhibitor0.9856
Renal organic cation transporterNon-inhibitor0.8959
CYP450 2C9 substrateNon-substrate0.8416
CYP450 2D6 substrateSubstrate0.5468
CYP450 3A4 substrateNon-substrate0.6826
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9163
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9379
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9537
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8691
BiodegradationNot ready biodegradable0.8969
Rat acute toxicity2.0932 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.996
hERG inhibition (predictor II)Non-inhibitor0.8861
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
Mass Spectrum (Electron Ionization)MSsplash10-00e9-9000000000-6a38697da7945fdb1908
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0uy0-0950000000-e882b8032954e2a624cf
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0076-4920000000-3c7f23b7695e5c4dcc4c
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0aos-9800000000-93a18f0e030605aa10aa
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-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01b9-6980000000-3a2af9caa0ddc645756a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0290000000-0e1f60f7eeef06627206
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-dda902f75e8d8e525d4f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-32b90aea04b68bdedbef
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-f333c3bfc9bd6c0593d4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004l-0890000000-5c0a8df3cdde41f290f2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0090000000-58fd12e8cca5ee837799
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0090000000-271732f56fff3c9ecf87
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014l-3960000000-ee2e8e341081d16f5fdb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-006t-3900000000-ff916216d2f4fc373c18
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-007k-3900000000-7ce05e231c161678a1d9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a5a-4900000000-4d9ba2cbcfaa9a4fd7fc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0090000000-326ded7fdf97f0b34fc5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0090000000-bb7e0317c8b0c0a5abbc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014l-3960000000-7c774d4cb55b5368392a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-3900000000-dc6f8a2d1c6ae9efff3d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-007k-3900000000-f1650653e39b75e13fa3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0532-3900000000-31769a32574200bca4e2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004l-0890000000-aae1100750adfa742e9b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0090000000-bfc82de3e4f68d57fc3a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01ba-7950000000-507b336f1f79bec366f2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0aba-9800000000-3a08c4ef10edc4fb0bb0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-006t-2900000000-618ffd9706a09b5a63a3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000t-2900000000-fbfd48146105ca4959d3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-002f-0980000000-1c21805f715b600204b2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-002f-0980000000-0e0a07b984863b6487b0
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004l-0890000000-0b8ed14c1fe8c5a81255
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004l-0890000000-55a81270bd88170a11fb
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-001i-0090000000-d5916c30a1b4d703c5db
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0290000000-6e3398eb8fe4bbd67783
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0290000000-40359fd567f74abb7b74
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-3910000000-43ae37638a8827ea76f1
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylacetamides
Direct Parent
Phenylacetamides
Alternative Parents
Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Secondary alcohols / Primary carboxylic acid amides / Amino acids and derivatives / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Organic oxides
show 2 more
Substituents
Phenylacetamide / Phenoxy compound / Phenol ether / Alkyl aryl ether / 1,2-aminoalcohol / Amino acid or derivatives / Carboxamide group / Secondary alcohol / Primary carboxylic acid amide / Carboxylic acid derivative
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid amide, ethanolamines, propanolamine (CHEBI:2904)

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. Schafer M, Frischkopf K, Taimor G, Piper HM, Schluter KD: Hypertrophic effect of selective beta(1)-adrenoceptor stimulation on ventricular cardiomyocytes from adult rat. Am J Physiol Cell Physiol. 2000 Aug;279(2):C495-503. [PubMed:10913016]
  2. Brown RA, Ilg KJ, Chen AF, Ren J: Dietary Mg(2+) supplementation restores impaired vasoactive responses in isolated rat aorta induced by chronic ethanol consumption. Eur J Pharmacol. 2002 May 10;442(3):241-50. [PubMed:12065078]
  3. Horinouchi T, Morishima S, Tanaka T, Suzuki F, Tanaka Y, Koike K, Miwa S, Muramatsu I: Different changes of plasma membrane beta-adrenoceptors in rat heart after chronic administration of propranolol, atenolol and bevantolol. Life Sci. 2007 Jul 12;81(5):399-404. Epub 2007 Jun 16. [PubMed:17628611]
  4. Alberti C, Monopoli A, Casati C, Forlani A, Sala C, Nador B, Ongini E, Morganti A: Mechanism and pressor relevance of the short-term cardiovascular and renin excitatory actions of the selective A2A-adenosine receptor agonists. J Cardiovasc Pharmacol. 1997 Sep;30(3):320-4. [PubMed:9300315]
  5. 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
Unknown
Actions
Inhibitor
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. 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. [PubMed:12795776]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
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. Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [PubMed:17125412]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [PubMed:14732961]
  3. Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [PubMed:27836712]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
  1. Takara K, Kakumoto M, Tanigawara Y, Funakoshi J, Sakaeda T, Okumura K: Interaction of digoxin with antihypertensive drugs via MDR1. Life Sci. 2002 Feb 15;70(13):1491-500. [PubMed:11895100]
  2. Neuhoff S, Ungell AL, Zamora I, Artursson P: pH-dependent bidirectional transport of weakly basic drugs across Caco-2 monolayers: implications for drug-drug interactions. Pharm Res. 2003 Aug;20(8):1141-8. [PubMed:12948010]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]

Drug created on June 13, 2005 07:24 / Updated on September 22, 2018 22:21