Basic Info

Common NameAtenolol(F04843)
2D Structure
Description

Atenolol is a so-called beta1-selective (or 'cardioselective') drug. That means that it exerts greater blocking activity on myocardial beta1-receptors than on beta2 ones in the lung. The beta2 receptors are responsible to keep the bronchial system open. If these receptors are blocked, bronchospasm with serious lack of oxygen in the body can result. However, due to its cardioselective properties, the risk of bronchospastic reactions if using atenolol is reduced compared to nonselective drugs as propranolol. Nonetheless, this reaction may also be encountered with atenolol, particularly with high doses. Extreme caution should be exerted if atenolol is given to asthma patients, who are particularly at risk; the dose should be as low as possible. If an asthma attack occurs, the inhalation of a beta2-mimetic antiasthmatic, such as hexoprenalin or salbutamol, will usually suppress the symptoms. Atenolol (trade name Tenormin) can be used to treat cardiovascular diseases such as hypertension, coronary heart disease, arrhythmias, and treatment of myocardial infarction after the acute event. Patients with compensated congestive heart failure may be treated with atenolol as a co medication (usually together with an ACE inhibitor, a diuretic and a digitalis-glycoside, if indicated). In patients with congestive heart failure, it reduces the need for and the consumption of oxygen of the heart muscle. It is very important to start with low doses, as atenolol reduces also the muscular power of the heart, which is an undesired effect in congestive heart failure.

FRCD IDF04843
CAS Number29122-68-7
PubChem CID2249
FormulaC14H22N2O3
IUPAC Name

2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide

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)

Canonical SMILES

CC(C)NCC(COC1=CC=C(C=C1)CC(=O)N)O

Isomeric SMILES

CC(C)NCC(COC1=CC=C(C=C1)CC(=O)N)O

WikipediaAtenolol
Synonyms
        
            atenolol
        
            29122-68-7
        
            Tenormin
        
            Tenormine
        
            Normiten
        
            Blokium
        
            Prenormine
        
            Tenoblock
        
            Atehexal
        
            Betablok
        
Classifies
                

                  
                    Illegal Additives
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenylacetamides
Intermediate Tree NodesNot available
Direct ParentPhenylacetamides
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenylacetamide - 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 - Secondary amine - Secondary aliphatic amine - Ether - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organopnictogen compound - Amine - Organic oxygen compound - Alcohol - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.

Properties

Property NameProperty Value
Molecular Weight266.341
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count8
Complexity263
Monoisotopic Mass266.163
Exact Mass266.163
XLogP0.2
Formal Charge0
Heavy Atom Count19
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9505
Human Intestinal AbsorptionHIA+0.9831
Caco-2 PermeabilityCaco2-0.7922
P-glycoprotein SubstrateSubstrate0.6773
P-glycoprotein InhibitorNon-inhibitor0.9446
Non-inhibitor0.9856
Renal Organic Cation TransporterNon-inhibitor0.8959
Distribution
Subcellular localizationMitochondria0.8513
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8416
CYP450 2D6 SubstrateSubstrate0.5468
CYP450 3A4 SubstrateNon-substrate0.6826
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9163
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.9379
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9537
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9960
Non-inhibitor0.8861
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.8691
Fish ToxicityHigh FHMT0.6122
Tetrahymena Pyriformis ToxicityHigh TPT0.7120
Honey Bee ToxicityLow HBT0.6965
BiodegradationNot ready biodegradable0.8969
Acute Oral ToxicityIII0.7976
Carcinogenicity (Three-class)Non-required0.7116

Model Value Unit
Absorption
Aqueous solubility-2.0111LogS
Caco-2 Permeability0.5609LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0932LD50, mol/kg
Fish Toxicity2.0488pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.4589pIGC50, ug/L

References

TitleJournalDatePubmed ID
Hypertension's 3 Dilemmas and 3 Solutions: Pharmacology of the Kidney inHypertension.J Cardiovasc Pharmacol2017 Mar28267687
An analysis of the dissipation of pharmaceuticals under thirteen different soilconditions.Sci Total Environ2016 Feb 1526657382
Pharmacological characteristics of Artemisia vulgaris L. in isolated porcinebasilar artery.J Ethnopharmacol2016 Apr 2226875644
Reactivity of β-blockers/agonists with aqueous permanganate. Kinetics and transformation products of salbutamol.Water Res2015 Aug 125965887
A new approach to predict human intestinal absorption using porcine intestinaltissue and biorelevant matrices.Eur J Pharm Sci2014 Oct 1525046168
Assessment of ABCG2-mediated transport of xenobiotics across the blood-milk barrier of dairy animals using a new MDCKII in vitro model.Arch Toxicol2013 Sep23652544
Effect of pharmaceuticals exposure on acetylcholinesterase (AchE) activity and on the expression of AchE gene in the monogonont rotifer, Brachionus koreanus.Comp Biochem Physiol C Toxicol Pharmacol2013 Nov24028855
Update on treatment of essential tremor.Curr Treat Options Neurol2013 Aug23881742
Pharmaco-nutrient interactions - a systematic review of zinc and antihypertensivetherapy.Int J Clin Pract2013 Aug23279674
Emerging pollutants in sewage, surface and drinking water in Galicia (NW Spain).Chemosphere2012 Mar22189380
Runoff of pharmaceuticals and personal care products following application of dewatered municipal biosolids to an agricultural field.Sci Total Environ2009 Aug 119464726
Use of toxicity assays for enantiomeric discrimination of pharmaceutical substances.Chirality2009 Aug18989896
[Arterial hypertension in pregnancy].Rev Med Brux2008 Sep18949985
A pharmacodynamic study on clenbuterol-induced toxicity: beta1- and beta2-adrenoceptors involvement in guinea-pig tachycardia in an in vitro model.Food Chem Toxicol2007 Sep17449161
A pilot study of open label sesame oil in hypertensive diabetics.J Med Food2006 Fall17004907
Perinatal MSG treatment attenuates fasting-induced bradycardia and metabolicsuppression.Physiol Behav2005 Oct 1516153669
Atenolol developmental toxicity: animal-to-human comparisons.Birth Defects Res A Clin Mol Teratol2003 Mar12797460
Capillary isotachophoresis/NMR: extension to trace impurity analysis and improvedinstrumental coupling.Anal Chem2002 May 1512038755
Dietary Mg(2+) supplementation restores impaired vasoactive responses in isolatedrat aorta induced by chronic ethanol consumption.Eur J Pharmacol2002 May 1012065078
Trial of antihypertensive intervention and management: greater efficacy withweight reduction than with a sodium-potassium intervention.J Am Diet Assoc1993 Apr8454808

Targets

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 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
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. [12795776 ]
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 equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
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.
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]