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Record Information
Version2.0
Creation Date2009-07-30 17:58:38 UTC
Update Date2014-12-24 20:26:07 UTC
Accession NumberT3D3480
Identification
Common NameAtenolol
ClassSmall Molecule
DescriptionAtenolol 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.
Compound Type
  • Adrenergic Agent
  • Adrenergic beta-1 Receptor Antagonist
  • Adrenergic beta-Antagonist
  • Amide
  • Amine
  • Anti-Arrhythmia Agent
  • Antihypertensive Agent
  • Drug
  • Ether
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Sympatholytic
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
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
Aircrit
Alinor
Altol
Anselol
Antipressan
Apo-Atenolol
Atcardil
Atecard
Atehexal
Atenblock
Atendol
Atenet
Ateni
Atenil
Atenol 1A pharma
Atenol acis
Atenol AL
Atenol Atid
Atenol Cophar
Atenol ct
Atenol Fecofar
Atenol Gador
Atenol Genericon
Atenol GNR
Atenol Heumann
Atenol MSD
Atenol NM Pharma
Atenol Nordic
Atenol PB
Atenol Quesada
Atenol Stada
Atenol Tika
Atenol Trom
Atenol von ct
Atenol-Mepha
Atenol-ratiopharm
Atenol-Wolff
Atenolin
Atenololum
Atenomel
Atereal
Aterol
Betablok
Betacard
Betasyn
Betatop Ge
Blocotenol
Blokium
Cardaxen
Cardiopress
Corotenol
Cuxanorm
Duraatenolol
Duratenol
Evitocor
Farnormin
Felo-Bits
Hipres
Hypoten
Ibinolo
Internolol
Jenatenol
Juvental
Lo-ten
Loten
Lotenal
Myocord
Normalol
Normiten
Noten
Oraday
Ormidol
Panapres
Plenacor
Premorine
Prenolol
Prenormine
Prinorm
Scheinpharm Atenol
Seles beta
Selobloc
Serten
Servitenol
Stermin
Tenidon
Tenobloc
Tenoblock
Tenolol
Tenoprin
Tenoretic
Tenormin
Tenormine
Tensimin
Tredol
Unibloc
Uniloc
Vascoten
Vericordin
Wesipin
Xaten
Chemical FormulaC14H22N2O3
Average Molecular Mass266.336 g/mol
Monoisotopic Mass266.163 g/mol
CAS Registry Number29122-68-7
IUPAC Name2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide
Traditional Nameatenolol
SMILESCC(C)NCC(O)COC1=CC=C(CC(O)=N)C=C1
InChI IdentifierInChI=1/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)
InChI KeyInChIKey=METKIMKYRPQLGS-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetamides
Direct ParentPhenylacetamides
Alternative Parents
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
  • 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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point158-160°C
Boiling PointNot Available
Solubility1.33E+004 mg/L (at 25°C)
LogP0.16
Predicted Properties
PropertyValueSource
Water Solubility0.43 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.51 m³·mol⁻¹ChemAxon
Polarizability29.98 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kmi-8920000000-75c70fad839dc47116bfJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9451000000-8069c1e0c4bc41c41dc5JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uy0-0950000000-e882b8032954e2a624cfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0076-4920000000-3c7f23b7695e5c4dcc4cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aos-9800000000-93a18f0e030605aa10aaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-3910000000-43ae37638a8827ea76f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-6980000000-3a2af9caa0ddc645756aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0290000000-0e1f60f7eeef06627206JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-dda902f75e8d8e525d4fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-32b90aea04b68bdedbefJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-f333c3bfc9bd6c0593d4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004l-0890000000-5c0a8df3cdde41f290f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-58fd12e8cca5ee837799JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-271732f56fff3c9ecf87JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014l-3960000000-ee2e8e341081d16f5fdbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-006t-3900000000-ff916216d2f4fc373c18JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-007k-3900000000-7ce05e231c161678a1d9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a5a-4900000000-4d9ba2cbcfaa9a4fd7fcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-326ded7fdf97f0b34fc5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-bb7e0317c8b0c0a5abbcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014l-3960000000-7c774d4cb55b5368392aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-1190000000-9c46f6de428fd9c85b0cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-5490000000-d3676c10983a2bf51eb7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9400000000-f879d668e69afad6eb16JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1590000000-21fbf983e89a88c8fda0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2910000000-55258981df3fe8b9c9edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-fc86b722c900f0c12c6fJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00e9-9000000000-6a38697da7945fdb1908JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureApproximately 50% of an oral dose is absorbed from the gastrointestinal tract, the remainder being excreted unchanged in the feces.
Mechanism of ToxicityLike 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.
MetabolismHepatic (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
Toxicity ValuesLD50: 2000-3000 mg/kg(oral, mice).
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the management of hypertention and long-term management of patients with angina pectoris
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of an atenolol overdose include a slow heart beat, shortness of breath, fainting, dizziness, weakness, confusion, nausea, and vomiting.
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00335
HMDB IDHMDB01924
PubChem Compound ID2249
ChEMBL IDCHEMBL24
ChemSpider ID2162
KEGG IDC13235
UniProt IDNot Available
OMIM ID
ChEBI ID2904
BioCyc IDNot Available
CTD IDNot Available
Stitch IDAtenolol
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkAtenolol
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.

MSDSLink
General References
  1. Drugs.com [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

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
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
  2. 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. [10913016 ]
  3. 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. [12065078 ]
  4. 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. [17628611 ]
  5. 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. [9300315 ]
  6. Smith C, Teitler M: Beta-blocker selectivity at cloned human beta 1- and beta 2-adrenergic receptors. Cardiovasc Drugs Ther. 1999 Apr;13(2):123-6. [10372227 ]
  7. Yasuda SU, Barbey JT, Funck-Brentano C, Wellstein A, Woosley RL: d-sotalol reduces heart rate in vivo through a beta-adrenergic receptor-independent mechanism. Clin Pharmacol Ther. 1993 Apr;53(4):436-42. [8386603 ]
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 ]
  2. Wisler JW, DeWire SM, Whalen EJ, Violin JD, Drake MT, Ahn S, Shenoy SK, Lefkowitz RJ: A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling. Proc Natl Acad Sci U S A. 2007 Oct 16;104(42):16657-62. Epub 2007 Oct 9. [17925438 ]