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Identification
NameAtenolol
Accession NumberDB00335  (APRD00172)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
1-p-Carbamoylmethylphenoxy-3-isopropylamino-2-propanolNot AvailableNot Available
2-(p-(2-Hydroxy-3-(isopropylamino)propoxy)phenyl)acetamideNot AvailableNot Available
4-(2-Hydroxy-3-((1-methylethyl)amino)propoxy)benzeneacetamideNot AvailableNot Available
AtenololumNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
MyocordIvax
NormitenTeva
TenorminAstraZeneca
Brand mixtures
Brand NameIngredients
Tenoreticatenolol + chlorthalidone
Categories
CAS number29122-68-7
WeightAverage: 266.3361
Monoisotopic: 266.16304258
Chemical FormulaC14H22N2O3
InChI KeyMETKIMKYRPQLGS-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenol Ethers
Direct parentPhenol Ethers
Alternative parentsAlkyl Aryl Ethers; Primary Carboxylic Acid Amides; Secondary Alcohols; 1,2-Aminoalcohols; Dialkylamines; Carboxylic Acids; Polyamines; Enolates
Substituentsalkyl aryl ether; 1,2-aminoalcohol; primary carboxylic acid amide; carboxamide group; secondary alcohol; polyamine; secondary amine; secondary aliphatic amine; enolate; carboxylic acid derivative; ether; carboxylic acid; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Pharmacology
IndicationFor the management of hypertention and long-term management of patients with angina pectoris
PharmacodynamicsAtenolol, 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 actionLike 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.
AbsorptionApproximately 50% of an oral dose is absorbed from the gastrointestinal tract, the remainder being excreted unchanged in the feces.
Volume of distributionNot Available
Protein bindingPlasma protein binding is 6-16%
Metabolism

Hepatic (minimal)

Route of eliminationApproximately 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 life6-7 hours
ClearanceNot Available
ToxicityLD50=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
PathwaysNot Available
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Beta-1 adrenergic receptor
Gene symbol: ADRB1
UniProt: P08588
rs1801253 Not AvailableG > CBetter response to drug therapy22192668
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9831
Blood Brain Barrier - 0.9505
Caco-2 permeable - 0.7922
P-glycoprotein substrate Substrate 0.6773
P-glycoprotein inhibitor I Non-inhibitor 0.9446
P-glycoprotein inhibitor II Non-inhibitor 0.9856
Renal organic cation transporter Non-inhibitor 0.8959
CYP450 2C9 substrate Non-substrate 0.8416
CYP450 2D6 substrate Substrate 0.5468
CYP450 3A4 substrate Non-substrate 0.6826
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9163
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.9379
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9537
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.8691
Biodegradation Not ready biodegradable 0.8969
Rat acute toxicity 2.0932 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.996
hERG inhibition (predictor II) Non-inhibitor 0.8861
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
Dosage forms
FormRouteStrength
InjectionIntravenous0.5 mg/ml
TabletOral25 mg, 50 mg, 100 mg
Prices
Unit descriptionCostUnit
Atenolol powder5.14USDg
Tenormin 100 mg tablet2.28USDtablet
Tenormin 25 mg tablet1.94USDtablet
Tenormin 50 mg tablet1.52USDtablet
Atenolol 100 mg tablet1.26USDtablet
Atenolol 50 mg tablet0.85USDtablet
Atenolol 25 mg tablet0.81USDtablet
Apo-Atenol 100 mg Tablet0.6USDtablet
Co Atenolol 100 mg Tablet0.6USDtablet
Mylan-Atenolol 100 mg Tablet0.6USDtablet
Novo-Atenol 100 mg Tablet0.6USDtablet
Phl-Atenolol 100 mg Tablet0.6USDtablet
Pms-Atenolol 100 mg Tablet0.6USDtablet
Ran-Atenolol 100 mg Tablet0.6USDtablet
Ratio-Atenolol 100 mg Tablet0.6USDtablet
Sandoz Atenolol 100 mg Tablet0.6USDtablet
Apo-Atenol 50 mg Tablet0.36USDtablet
Co Atenolol 50 mg Tablet0.36USDtablet
Mylan-Atenolol 50 mg Tablet0.36USDtablet
Novo-Atenol 50 mg Tablet0.36USDtablet
Phl-Atenolol 50 mg Tablet0.36USDtablet
Pms-Atenolol 50 mg Tablet0.36USDtablet
Ran-Atenolol 50 mg Tablet0.36USDtablet
Ratio-Atenolol 50 mg Tablet0.36USDtablet
Sandoz Atenolol 50 mg Tablet0.36USDtablet
Novo-Atenol 25 mg Tablet0.18USDtablet
Pms-Atenolol 25 mg Tablet0.18USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point158-160Barrett, 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 Solubility0.429ALOGPS
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
Spectra
SpectraMS/MS1D NMR2D NMR
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 ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00235
PubChem Compound2249
PubChem Substance46506915
ChemSpider2162
BindingDB25753
ChEBI2904
ChEMBLCHEMBL24
Therapeutic Targets DatabaseDAP000482
PharmGKBPA448499
IUPHAR548
Guide to Pharmacology548
Drug Product Database828793
RxListhttp://www.rxlist.com/cgi/generic/atenolol.htm
Drugs.comhttp://www.drugs.com/atenolol.html
WikipediaAtenolol
ATC CodesC07AB03C07AB11
AHFS Codes
  • 24:24.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(72.9 KB)
Interactions
Drug Interactions
Drug
AcetohexamideThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
AmpicillinAmpicillin decreases bioavailability of atenolol
ChlorpropamideThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
ClonidineIncreased hypertension when clonidine stopped
DihydroergotamineIschemia with risk of gangrene
DiltiazemIncreased risk of bradycardia
DisopyramideThe beta-blocker, atenolol, may increase the toxicity of disopyramide.
EpinephrineHypertension, then bradycardia
ErgonovineIschmeia with risk of gangrene
ErgotamineIschemia with risk of gangrene
FenoterolAntagonism
FormoterolAntagonism
GliclazideThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
GlipizideThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
GlisoxepideThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
GlyburideThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
GlycodiazineThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
IbuprofenRisk of inhibition of renal prostaglandins
IndacaterolBeta-adrenergic antagonists, especially those that are not cardioselective, may interfere with the effect of indacaterol when administered concurrently. Beta-blockers may exacerbate bronchospasms in patients with COPD.
IndomethacinRisk of inhibition of renal prostaglandins
Insulin AspartThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
Insulin DetemirThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
Insulin GlargineThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
Insulin GlulisineThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
Insulin LisproThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
IsoprenalineAntagonism
LidocaineThe beta-blocker, atenolol, may increase the effect and toxicity of lidocaine.
MethysergideIschemia with risk of gangrene
OrciprenalineAntagonism
PipobromanAntagonism
PirbuterolAntagonism
PiroxicamRisk of inhibition of renal prostaglandins
PrazosinRisk of hypotension at the beginning of therapy
ProcaterolAntagonism
RepaglinideThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
SalbutamolAntagonism
SalmeterolAntagonism
TerazosinIncreased risk of hypotension. Initiate concomitant therapy cautiously.
TerbutalineAntagonism
TolazamideThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
TolbutamideThe beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
TreprostinilAdditive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
VerapamilIncreased effect of both drugs
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.

Targets

1. Beta-1 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

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
  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
  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
  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
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

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

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on March 31, 2014 11:08