Banner
targets (1) transporters (1)
for drugs
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. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Aircrit
  • Alinor
  • Altol
  • Anselol
  • Antipressan
  • Apo-Atenolol
  • Atcardil
  • Atecard
  • Atehexal
  • Atenblock
  • Atendol
  • Atenet
  • Ateni
  • Atenil
  • Atenol
  • 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
  • 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
  • Teno-Basan
  • Tenobloc
  • Tenoblock
  • Tenolol
  • Tenoprin
  • Tenormin
  • Tenormine
  • Tensimin
  • Tredol
  • Unibloc
  • Uniloc
  • Vascoten
  • Vericordin
  • Wesipin
  • Xaten
Brand name mixtures
  • Tenoretic (atenolol + chlorthalidone)
Categories
  • Antihypertensive Agents
  • Adrenergic Agents
  • Adrenergic beta-Antagonists
  • Sympatholytics
  • Antiarrhythmic Agents
  • Anti-Arrhythmia Agents
CAS number 29122-68-7
Weight Average: 266.3361
Monoisotopic: 266.163042580
Chemical Formula C14H22N2O3
InChI Key InChIKey=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)
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Ethers
  • Phenethylamines
  • Anisoles
Substructures
  • Hydroxy Compounds
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Amino Ketones
  • Ethers
  • Benzene and Derivatives
  • Carbamates and Derivatives
  • Amino Alcohols
  • Phenethylamines
  • Aromatic compounds
  • Anisoles
  • Carboxamides and Derivatives
  • Carboxylic Acids and Derivatives
  • Alcohols and Polyols
  • Phenyl Esters
Pharmacology
Indication For the management of hypertention and long-term management of patients with angina pectoris
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.
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
Pathway Name SMPDB ID
Smp00298 Atenolol Pathway SMP00298
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
Form Route Strength
Injection Intravenous 0.5 mg/ml
Tablet Oral 25 mg, 50 mg, 100 mg
Prices
Unit description Cost Unit
Atenolol powder 5.14 USD g
Tenormin 100 mg tablet 2.28 USD tablet
Tenormin 25 mg tablet 1.94 USD tablet
Tenormin 50 mg tablet 1.52 USD tablet
Atenolol 100 mg tablet 1.26 USD tablet
Atenolol 50 mg tablet 0.85 USD tablet
Atenolol 25 mg tablet 0.81 USD tablet
Apo-Atenol 100 mg Tablet 0.6 USD tablet
Co Atenolol 100 mg Tablet 0.6 USD tablet
Mylan-Atenolol 100 mg Tablet 0.6 USD tablet
Novo-Atenol 100 mg Tablet 0.6 USD tablet
Phl-Atenolol 100 mg Tablet 0.6 USD tablet
Pms-Atenolol 100 mg Tablet 0.6 USD tablet
Ran-Atenolol 100 mg Tablet 0.6 USD tablet
Ratio-Atenolol 100 mg Tablet 0.6 USD tablet
Sandoz Atenolol 100 mg Tablet 0.6 USD tablet
Apo-Atenol 50 mg Tablet 0.36 USD tablet
Co Atenolol 50 mg Tablet 0.36 USD tablet
Mylan-Atenolol 50 mg Tablet 0.36 USD tablet
Novo-Atenol 50 mg Tablet 0.36 USD tablet
Phl-Atenolol 50 mg Tablet 0.36 USD tablet
Pms-Atenolol 50 mg Tablet 0.36 USD tablet
Ran-Atenolol 50 mg Tablet 0.36 USD tablet
Ratio-Atenolol 50 mg Tablet 0.36 USD tablet
Sandoz Atenolol 50 mg Tablet 0.36 USD tablet
Novo-Atenol 25 mg Tablet 0.18 USD tablet
Pms-Atenolol 25 mg Tablet 0.18 USD tablet
Patents Not Available
Properties
State solid
Melting point 146-148oC
Experimental Properties
Property Value Source
water solubility 13.5 mg/mL PhysProp
logP 0.5 PhysProp
Caco2 permeability -6.44 [ADME Research, USCD] BiGG
Predicted Properties
Property Value Source
water solubility 4.29e-01 g/l ALOGPS
logP 0.57 ALOGPS
logP 0.43 ChemAxon Molconvert
logS -2.79 ALOGPS
pKa 15.95 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 84.58 ChemAxon Molconvert
rotatable bond count 8 ChemAxon Molconvert
refractivity 73.51 ChemAxon Molconvert
polarizability 29.98 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00235 Link_out
PubChem Compound 2249 Link_out
PubChem Substance 46506915 Link_out
ChemSpider 2162 Link_out
BindingDB 25753 Link_out
ChEBI 2904 Link_out
ChEMBL 2904 Link_out
Therapeutic Targets Database DAP000482 Link_out
Drug Product Database 828793 Link_out
RxList http://www.rxlist.com/cgi/generic/atenolol.htm Link_out
Drugs.com http://www.drugs.com/atenolol.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Atenolol Link_out
ATC Codes
  • C07AB03
  • C07AB11
AHFS Codes
  • 24:24.00
PDB Entries Not Available
FDA label Not Available
MSDS show (72.9 KB)
Interactions
Drug Interactions Not Available
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

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Transporters

1. Multidrug resistance protein 1

Actions: substrate, inhibitor

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out
Gene: ABCB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:02

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.