Atenolol

Identification

Summary

Atenolol is a synthetic beta-1 selective blocker used in the management of hypertension and chronic angina, and to reduce mortality in known or suspected myocardial infarction in hemodynamically stable patients.

Brand Names
Tenoretic, Tenormin
Generic Name
Atenolol
DrugBank Accession Number
DB00335
Background

Atenolol is a cardioselective beta-blocker used in a variety of cardiovascular conditions.

Sir James Black, a Scottish pharmacologist, pioneered the use of beta-blockers for the management of angina pectoris in 1958 for which he received the Nobel Prize.19 Beta-blockers quickly became popular in clinical use and where subsequently investigated for use in myocardial infarction, arrhythmias, and hypertension during the 1960s. Later they continued to be investigated for use in heart failure throughout the 1970-1980s. Atenolol itself was developed early on in this history by Alvogen Malta under the trade name Tenormin and received FDA approval in September, 1981.Label

Despite being one of the most widely prescribed beta blockers, evidence suggests atenolol may not significantly reduce mortality, and only modestly reduce the risk of cardiovascular disease in patients with hypertension.20,21 A Cochrane review of patients being treated for primary hypertension shows that atenolol shows a risk ratio of 0.88 for cardiovascular disease risk and a risk ratio of 0.99 for mortality.20,21 Similar results have been found in other meta-analyses.22,23 A meta-analysis of over 145,000 patients showed the risk of stroke in patients taking atenolol may depend on the age of the patient.23 The use of atenolol may need to be based on more patient factors than hypertension alone.20,21,22,23

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 266.3361
Monoisotopic: 266.16304258
Chemical Formula
C14H22N2O3
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
  • Atenolol
  • Atenololum

Pharmacology

Indication

Indicated for:Label

1) Management of hypertension alone and in combination with other antihypertensives.

2) Management of angina pectoris associated with coronary atherosclerosis.

3) Management of acute myocardial infarction in hemodynamically stable patients with a heart rate greater than 50 beats per minutes and a systolic blood pressure above 100 mmHg.

Off-label uses include:

1) Secondary prevention of myocardial infarction.4

2) Management of heart failure.3

3) Management of atrial fibrillation.1

4) Management of supraventricular tachycardia.5

5) Management of ventricular arrythmias such as congenital long-QT and arrhythmogenic right ventricular cardiomyopathy.6

6) Management of symptomatic thyrotoxicosis in combination with methimazole.2

7) Prophylaxis of migraine headaches.7

8) Management of alcohol withdrawal.8,9

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAlcohol withdrawal••• •••••••••••
Management ofAngina pectoris••••••••••••••••••
Management ofAtrial fibrillation••• ••••••••••••••••
Management ofHeart failure••• •••••••••••
Management ofHypertension••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Atenolol is a cardio-selective beta-blocker and as such exerts most of its effects on the heart.Label It acts as an antagonist to sympathetic innervation and prevents increases in heart rate, electrical conductivity, and contractility in the heart due to increased release of norepinephrine from the peripheral nervous system.Label,24,14 Together the decreases in contractility and rate produce a reduction in cardiac output resulting in a compensatory increase in peripheral vascular resistance in the short-term. This response later declines to baseline with long-term use of atenolol. More importantly, this reduction in the work demanded of the myocardium also reduces oxygen demand which provides therapeutic benefit by reducing the mismatch of oxygen supply and demand in settings where coronary blood flow is limited, such as in coronary atherosclerosis. Reducing oxygen demand, particularly due to exercise, can reduce the frequency of angina pectoris symptoms and potentially improve survival of the remaining myocardium after myocardial infarction. The decrease in rate of sinoatrial node potentials, electrical conduction, slowing of potentials traveling through the atrioventricular node, and reduced frequency of ectopic potentials due to blockade of adrenergic beta receptors has led to benefit in arrhythmic conditions such as atrial fibrillation by controlling the rate of action potential generation and allowing for more effective coordinated contractions. Since a degree of sympathetic activity is necessary to maintain cardiac function, the reduced contractility induced by atenolol may precipitate or worsen heart failure, especially during volume overload.Label

The effects of atenolol on blood pressure have been established, although it is less effective than alternative beta-blockers, but the mechanism has not yet been characterized.Label,24 As a β1 selective drug, it does not act via the vasodilation produced by non-selective agents.24 Despite this there is a sustained reduction in peripheral vascular resistance, and consequently blood pressure, alongside a decrease in cardiac output. It is thought that atenolol's antihypertensive activity may be related to action on the central nervous system (CNS) or it's inhibition of the renin-aldosterone-angiotensin system rather than direct effects on the vasculature.Label

Atenolol produces CNS effects similar to other beta-blockers, but does so to a lesser extent due to reduces ability to cross the blood-brain barrier.24 It has the potential to produce fatigue, depression, and sleep disturbances such as nightmares or insomnia.Label,24 The exact mechanisms behind these have not been characterized but their occurrence must be considered as they represent clinically relevant adverse effects.

Atenolol exerts some effects on the respiratory system although to a much lesser extent than non-selective beta-blockers.Label Interaction with β2 receptors in the airways can produce bronchoconstriction by blocking the relaxation of bronchial smooth muscle mediated by the sympathetic nervous system.24 The same action can interfere with β-agonist therapies used in asthma and chronic obstructive pulmonary disease.Label,14,24

Unlike some other beta-blocker drugs, atenolol does not have intrinsic sympathomimetic or membrane stabilizing activity nor does it produce changes in glycemic control.Label

Mechanism of action

Atenolol is a cardioselective beta-blocker, called such because it selectively binds to the β1-adrenergic receptor as an antagonist up to a reported 26 fold more than β2 receptors.15 Selective activity at the β1 receptor produces cardioselectivity due to the higher population of this receptor in cardiac tissue. Some binding to β2 and possibly β3 receptors can still occur at therapeutic dosages but the effects mediated by antagonizing these are significantly reduced from those of non-selective agents. β1 and β2 receptors are Gs coupled therefore antagonism of their activation reduces activity of adenylyl cyclase and its downstream signalling via cyclic adenosime monophosphate and protein kinase A (PKA).

In cardiomyocytes PKA is thought to mediate activation of L-type calcium channels and ryanodine receptors through their phosphorylation.16 L-type calcium channels can then provide an initial rise in intracellular calcium and trigger the ryanodine receptors to release calcium stored in the sarcoplasmic reticulum (SR) and increased contractility. PKA also plays a role in the cessation of contraction by phosphorylating phospholamban which in turn increases the affinity of SR Ca2+ ATPase to increase reuptake of calcium into the SR. It also phophorylates troponin I to reduce affinity of the protein for calcium. Both of these events lead to a reduction in contraction which, when coupled with the initial increase in contraction, allows for faster cycling and consequently higher heart rate with increased contractility. L-type calcium channels are also a major contributor to cardiac depolarization and their activation can increase frequency of action potentials and possibly the incidence of ectopic potentials.17

Similar inihibitory events occur in the bronchial smooth muscle to mediate relaxation including phosphorylation of myosin light-chain kinase, reducing its affinity for calcium.18 PKA also inhibits the excitatory Gq coupled pathway by phosphorylating the inositol trisphosphate receptor and phospholipase C resulting in inhibition of intracellular calcium release. Antagonism of this activity by beta-blocker agents like atenolol can thus cause increased bronchoconstriction.

TargetActionsOrganism
ABeta-1 adrenergic receptor
antagonist
Humans
UBeta-2 adrenergic receptor
antagonist
Humans
Absorption

Approximately 50% of an oral dose is absorbed from the gastrointestinal tract, with the remainder being excreted unchanged in the feces.Label Administering atenolol with food can decrease the AUC by about 20%.10 While atenolol can cross the blood-brain barrier, it does so slowly and to a small extent.

Volume of distribution

Total Vd of 63.8-112.5 L. Atenolol distributes into a central volume of 12.8-17.5 L along with two peripheral compartments with a combined volume of 51-95 L.10 Distribution takes about 3 hrs for the central compartment, 4 hrs for the shallower peripheral compartment, and 5-6 hrs for the deeper peripheral compartment.

Protein binding

6-16% bound in plasma.Label Atenolol binds to two sites on human serum albumin.12

Metabolism

Minimal metabolism in the liver.Label The sole non-conjugated metabolite is the product of a hydroxylation reaction at the carbon between the amide and benzene groups.11 The only other metabolite to be confirmed is a glucuronide conjugate. These metabolites make up 5-8% and 2% of the renally excreted dose with 87-90% appearing as unchanged drug. The hydroxylated metabolite is exerts 1/10th the beta-blocking activity of atenolol.

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Route of elimination

85% is eliminated by the kidneys following IV administration with 10% appearing in the feces.Label,10

Half-life

6-7 hrs.Label

Clearance

Total clearance is estimated at 97.3-176.3 mL/min with a renal clearance of 95-168 mL/min.10

Adverse Effects
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Toxicity

LD50 Values

Mouse: 2 g/kg (Oral), 57 mg/kg (IV), 134 mg/kg (IP), 400 mg/kg (SC)26

Rat: 2 g/kg (Oral), 77 mg/kg (IV), 600 mg/kg (SC)26

Rabbit: 50 mg/kg (IV)26

Carcinogenicity & Mutagenicity

Studies in rats and mice at doses of 300 mg/kg/day, equivalent to 150 times maximum recommended human dose, for durations of 18 and 24 months showed no carcinogenicity.Label One study in rats at doses of 500-1500 mg/kg/day, 250-750 times maximum human dose, resulted in increases benign adrenal medullary tumors in both sexes and increase mammary fibroadenomas in females.

Atenolol showed no mutagenicity in the Ames test using S. typhinarium, dominant lethal test in mice, or in vivo cytogenetics test in chinese hamster ovary cells.Label

Reproductive Toxicity

No adverse effects on fertility were observed in either male or female mice after receiving doses of 200 mg/kg/day, equivalent to 200 times the maximum human dose. In humans, atenolol is known to cross the placenta and fetuses exposed to the drug have been reported to be smaller than expected considering gestational age. Embryo-fetal resorption has been observed in rats at doses of 50mg/kg/day, 50 times the max human dose, but not in rabbits at doses of 25mg/kg/day.Label

Lactation

Atenolol appears in breast milk at a ratio of 1.5-6.8 to plasma concentrations.Label It has been estimated that infant exposure occurs at 5.7-19.2% maternal weight-adjusted dosage.25 Effects in infants include bradycardia, hypothermia, and lethargy.

Pathways
PathwayCategory
Atenolol Action PathwayDrug action
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
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 Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Atenolol is combined with Abaloparatide.
AbataceptThe metabolism of Atenolol can be increased when combined with Abatacept.
AbirateroneThe metabolism of Atenolol can be decreased when combined with Abiraterone.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Atenolol.
AcebutololAtenolol may increase the arrhythmogenic activities of Acebutolol.
Food Interactions
No interactions found.

Products

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Product Images
International/Other Brands
Myocord (Ivax) / Normiten (Teva)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act AtenololTablet50 mgOralActavis Pharma Company2004-08-132020-10-21Canada flag
Act AtenololTablet100 mgOralActavis Pharma Company2004-08-132020-10-21Canada flag
AtenololTablet100 mgOralMeliapharm Inc2011-04-082014-06-25Canada flag
AtenololTablet25 mgOralSivem Pharmaceuticals UlcNot applicableNot applicableCanada flag
AtenololTablet100 mg/1OralWatson Pharmaceuticals2007-03-02Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-atenololTablet50 mgOralAngita Pharma Inc.2018-07-18Not applicableCanada flag
Ag-atenololTablet25 mgOralAngita Pharma Inc.2018-07-18Not applicableCanada flag
Ag-atenololTablet100 mgOralAngita Pharma Inc.2018-07-18Not applicableCanada flag
Apo-atenol Tab 100mgTablet100 mgOralApotex Corporation1988-12-31Not applicableCanada flag
Apo-atenol Tab 50mgTablet50 mgOralApotex Corporation1988-12-31Not applicableCanada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PRENOLOL 50Tablet, coated50 mgOralบริษัท เบอร์ลินฟาร์มาซูติคอลอินดัสตรี้ จำกัด2016-09-13Not applicableThailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Aa-atenidoneAtenolol (50 mg) + Chlorthalidone (25 mg)TabletOralAa Pharma Inc2004-08-12Not applicableCanada flag
Aa-atenidoneAtenolol (100 mg) + Chlorthalidone (25 mg)TabletOralAa Pharma Inc2004-08-12Not applicableCanada flag
Apo-Atenidone Tablets 100/25 mgAtenolol (100 mg) + Chlorthalidone (25 mg)TabletOralPHARMAFORTE (MALAYSIA) SDN. BHD.2020-09-08Not applicableMalaysia flag
ATENIGRONAtenolol (125 mg) + Chlorthalidone (25 mg)TabletOralAescul API Us Farmaceutici Srl2014-07-082023-12-08Italy flag
ATENIGRONAtenolol (125 mg) + Chlorthalidone (25 mg)TabletOralAescul API Us Farmaceutici Srl2014-07-082023-12-08Italy flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Atenolol ScopolamineAtenolol (50 mg/50.5mg) + Scopolamine (.5 mg/50.5mg)TabletOralTPS2014-10-01Not applicableUS flag
Atenolol ScopolamineAtenolol (25 mg/25.25mg) + Scopolamine (.25 mg/25.25mg)TabletBuccal; Oral; Sublingual; TransmucosalTPS2014-10-01Not applicableUS flag

Categories

ATC Codes
C07CB53 — Atenolol and other diuretics, combinationsC07AB03 — AtenololC07FB03 — Atenolol and nifedipineC07DB01 — Atenolol, thiazides and other diureticsC07BB03 — Atenolol and thiazidesC07CB03 — Atenolol and other diuretics
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Amino acid or derivatives / Aromatic homomonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Ether
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid amide, ethanolamines, propanolamine (CHEBI:2904)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
50VV3VW0TI
CAS number
29122-68-7
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

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
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  3. Ezekowitz JA, O'Meara E, McDonald MA, Abrams H, Chan M, Ducharme A, Giannetti N, Grzeslo A, Hamilton PG, Heckman GA, Howlett JG, Koshman SL, Lepage S, McKelvie RS, Moe GW, Rajda M, Swiggum E, Virani SA, Zieroth S, Al-Hesayen A, Cohen-Solal A, D'Astous M, De S, Estrella-Holder E, Fremes S, Green L, Haddad H, Harkness K, Hernandez AF, Kouz S, LeBlanc MH, Masoudi FA, Ross HJ, Roussin A, Sussex B: 2017 Comprehensive Update of the Canadian Cardiovascular Society Guidelines for the Management of Heart Failure. Can J Cardiol. 2017 Nov;33(11):1342-1433. doi: 10.1016/j.cjca.2017.08.022. Epub 2017 Sep 6. [Article]
  4. Mancini GB, Gosselin G, Chow B, Kostuk W, Stone J, Yvorchuk KJ, Abramson BL, Cartier R, Huckell V, Tardif JC, Connelly K, Ducas J, Farkouh ME, Gupta M, Juneau M, O'Neill B, Raggi P, Teo K, Verma S, Zimmermann R: Canadian Cardiovascular Society guidelines for the diagnosis and management of stable ischemic heart disease. Can J Cardiol. 2014 Aug;30(8):837-49. doi: 10.1016/j.cjca.2014.05.013. Epub 2014 May 28. [Article]
  5. Page RL, Joglar JA, Caldwell MA, Calkins H, Conti JB, Deal BJ, Estes NAM 3rd, Field ME, Goldberger ZD, Hammill SC, Indik JH, Lindsay BD, Olshansky B, Russo AM, Shen WK, Tracy CM, Al-Khatib SM: 2015 ACC/AHA/HRS Guideline for the Management of Adult Patients With Supraventricular Tachycardia: A Report of the American College of Cardiology/American Heart Association Task Force on Clinical Practice Guidelines and the Heart Rhythm Society. J Am Coll Cardiol. 2016 Apr 5;67(13):e27-e115. doi: 10.1016/j.jacc.2015.08.856. Epub 2015 Sep 24. [Article]
  6. Al-Khatib SM, Stevenson WG, Ackerman MJ, Bryant WJ, Callans DJ, Curtis AB, Deal BJ, Dickfeld T, Field ME, Fonarow GC, Gillis AM, Granger CB, Hammill SC, Hlatky MA, Joglar JA, Kay GN, Matlock DD, Myerburg RJ, Page RL: 2017 AHA/ACC/HRS Guideline for Management of Patients With Ventricular Arrhythmias and the Prevention of Sudden Cardiac Death. Circulation. 2018 Sep 25;138(13):e272-e391. doi: 10.1161/CIR.0000000000000549. [Article]
  7. Jackson JL, Cogbill E, Santana-Davila R, Eldredge C, Collier W, Gradall A, Sehgal N, Kuester J: A Comparative Effectiveness Meta-Analysis of Drugs for the Prophylaxis of Migraine Headache. PLoS One. 2015 Jul 14;10(7):e0130733. doi: 10.1371/journal.pone.0130733. eCollection 2015. [Article]
  8. Horwitz RI, Gottlieb LD, Kraus ML: The efficacy of atenolol in the outpatient management of the alcohol withdrawal syndrome. Results of a randomized clinical trial. Arch Intern Med. 1989 May;149(5):1089-93. [Article]
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  10. Kirch W, Gorg KG: Clinical pharmacokinetics of atenolol--a review. Eur J Drug Metab Pharmacokinet. 1982;7(2):81-91. doi: 10.1007/BF03188723. [Article]
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  25. LactMed: Atenolol [Link]
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  27. FDA Approved Products: Tenormin (atenolol) oral tablets [Link]
Human Metabolome Database
HMDB0001924
KEGG Drug
D00235
PubChem Compound
2249
PubChem Substance
46506915
ChemSpider
2162
BindingDB
25753
RxNav
1202
ChEBI
2904
ChEMBL
CHEMBL24
Therapeutic Targets Database
DAP000482
PharmGKB
PA448499
Guide to Pharmacology
GtP Drug Page
RxList
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Drugs.com Drug Page
Wikipedia
Atenolol
FDA label
Download (226 KB)
MSDS
Download (72.9 KB)

Clinical Trials

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Pharmacoeconomics

Manufacturers
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  • 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
Tablet, film coatedOral
Tablet, film coatedOral
TabletOral100 mg/1
TabletOral25 mg/1
TabletOral50 mg/1
TabletOral
TabletOral10000000 mg
TabletOral
TabletBuccal; Oral; Sublingual; Transmucosal
SolutionOral
Tablet, coatedOral
TabletOral50.00 mg
Capsule, liquid filledOral100 mg
Capsule, liquid filledOral50 mg
Tablet, coatedOral
Capsule, extended releaseOral
CapsuleOral50 mg
CapsuleOral
TabletOral50 mg
TabletOral100 MG
Tablet, film coatedOral100 mg
Tablet, film coatedOral50 mg
Injection, solutionIntravenous5 mg/10mL
TabletOral5000000 mg
SolutionParenteral5 mg
Tablet, film coatedOral25 mg
TabletOral50.000 mg
TabletOral50 mg
Tablet, film coatedOral100 mg
Tablet, coatedOral25 mg
Tablet, film coatedOral50 mg
TabletOral25 mg
Tablet, coatedOral100 mg
Tablet, coatedOral50 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-MSsplash10-0kmi-8920000000-75c70fad839dc47116bf
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0002-3910000000-43ae37638a8827ea76f1
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-4cc40fb031de86458a46
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00l6-6940000000-c5dcc3052b29e5073b8f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-006t-9240000000-a57008e032c16a687b6d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-8900000000-4c8a7b4c28b4a9cdbc87
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9620000000-3aa59ad3cd05c53ef9ea
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9200000000-ffe42b0ff011269e048b
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-177.0360205
predicted
DarkChem Lite v0.1.0
[M-H]-163.46071
predicted
DeepCCS 1.0 (2019)
[M+H]+178.1194205
predicted
DarkChem Lite v0.1.0
[M+H]+165.81871
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.7919205
predicted
DarkChem Lite v0.1.0
[M+Na]+171.91185
predicted
DeepCCS 1.0 (2019)

Targets

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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
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. 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]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Curator comments
May be responsible for metabolizing a small portion of atenolol as CYP2D6 also metabolizes metoprolol, a strucurally similar molecule.
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 . [Article]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Niaei N, Hasanzadeh M, Shadjou N: Molecular interaction of some cardiovascular drugs with human serum albumin at physiological-like conditions: A new approach. J Mol Recognit. 2018 Aug;31(8):e2715. doi: 10.1002/jmr.2715. Epub 2018 Apr 6. [Article]

Transporters

Kind
Protein
Organism
Humans
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. [Article]

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