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Showing drug card for Atenolol (DB00335)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-04-16 16:47:37
Primary Accession Number DB00335
Secondary Accession Number
  • APRD00172
Name Atenolol
Drug Type
  • Approved
  • Small Molecule
Description A cardioselective beta-adrenergic blocker possessing properties and potency similar to propranolol, but without a negative inotropic effect. [PubChem]
Synonyms Not Available
Brand Names
  1. Aircrit
  2. Alinor
  3. Altol
  4. Anselol
  5. Antipressan
  6. Apo-Atenolol
  7. Atcardil
  8. Atecard
  9. Atehexal
  10. Atenblock
  11. Atendol
  12. Atenet
  13. Ateni
  14. Atenil
  15. Atenol
  16. Atenol 1A Pharma
  17. Atenol AL
  18. Atenol Acis
  19. Atenol Atid
  20. Atenol CT
  21. Atenol Cophar
  22. Atenol Fecofar
  23. Atenol GNR
  24. Atenol Gador
  25. Atenol Genericon
  26. Atenol Heumann
  27. Atenol MSD
  28. Atenol NM Pharma
  29. Atenol Nordic
  30. Atenol PB
  31. Atenol Quesada
  32. Atenol Stada
  33. Atenol Tika
  34. Atenol Trom
  35. Atenol Von CT
  36. Atenol-Mepha
  37. Atenol-Ratiopharm
  38. Atenol-Wolff
  39. Atenolin
  40. Atenomel
  41. Atereal
  42. Aterol
  43. Betablok
  44. Betacard
  45. Betasyn
  46. Betatop GE
  47. Blocotenol
  48. Blokium
  49. Cardaxen
  50. Cardiopress
  51. Corotenol
  52. Cuxanorm
  53. Duraatenolol
  54. Duratenol
  55. Evitocor
  56. Farnormin
  57. Felo-Bits
  58. Hipres
  59. Hypoten
  60. Ibinolo
  61. Internolol
  62. Jenatenol
  63. Juvental
  64. Lo-Ten
  65. Loten
  66. Lotenal
  67. Myocord
  68. Normalol
  69. Normiten
  70. Noten
  71. Oraday
  72. Ormidol
  73. Panapres
  74. Plenacor
  75. Premorine
  76. Prenolol
  77. Prenormine
  78. Prinorm
  79. Scheinpharm Atenol
  80. Seles Beta
  81. Selobloc
  82. Serten
  83. Servitenol
  84. Stermin
  85. Tenidon
  86. Teno-Basan
  87. Tenobloc
  88. Tenoblock
  89. Tenolol
  90. Tenoprin
  91. Tenormin
  92. Tenormine
  93. Tensimin
  94. Tredol
  95. Unibloc
  96. Uniloc
  97. Vascoten
  98. Vericordin
  99. Wesipin
  100. Xaten
Brand Mixtures
  1. Tenoretic (atenolol + chlorthalidone)
Chemical IUPAC Name 2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide
Chemical Formula C14H22N2O3
Chemical Structure Structure
CAS Registry Number 29122-68-7
InChI Identifier InChI=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)/f/h15H2
InChI Key METKIMKYRPQLGS-YHSKDTNECH
KEGG Drug D00235 Link Image
KEGG Compound Not Available
PubChem Compound 2249 Link Image
PubChem Substance 176216 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00828793 Link Image
RxList Link http://www.rxlist.com/cgi/generic/atenolol.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Atenolol Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Barrett et al., U.S. Pat. 3,,663,607 (1972)
Average Molecular Weight 266.3361
Monoisotopic Molecular Weight 266.1630
State Solid
Melting Point 146-148oC
Experimental Water Solubility 13.5 mg/mL Source: PhysProp
Predicted Water Solubility 4.29e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 0.5 Source: PhysProp
Predicted LogP 0.57 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.79 Calculated using ALOGPS
Experimental Caco2 Permeability -6.44 [ADME Research, USCD]
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1
Canonical SMILES CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1
Drug Category
  • Adrenergic Agents
  • Adrenergic beta-Antagonists
  • Anti-Arrhythmia Agents
  • Antiarrhythmic Agents
  • Antihypertensive Agents
  • Sympatholytics
ATC Codes
AHFS Codes
  • 24:24.00
Indication For the management of hypertention and long-term management of patients with angina pectoris
Pharmacology 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.
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.
Protein Binding Plasma protein binding is 6-16%
Biotransformation Hepatic (minimal)
Half Life 6-7 hours
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acetohexamide The beta-blocker decreases the symptoms of hypoglycemia
Ampicillin Ampicillin decreases bioavailability of atenolol
Chlorpropamide The beta-blocker decreases the symptoms of hypoglycemia
Clonidine Increased hypertension when clonidine stopped
Dihydroergotamine Ischemia with risk of gangrene
Dihydroergotoxine Ischemia with risk of gangrene
Diltiazem Increased risk of bradycardia
Disopyramide The beta-blocker increases toxicity of disopyramide
Epinephrine Hypertension, then bradycardia
Ergonovine Ischmeia with risk of gangrene
Ergotamine Ischemia with risk of gangrene
Fenoterol Antagonism
Formoterol Antagonism
Glibenclamide The beta-blocker decreases the symptoms of hypoglycemia
Gliclazide The beta-blocker decreases the symptoms of hypoglycemia
Glipizide The beta-blocker decreases the symptoms of hypoglycemia
Glisoxepide The beta-blocker decreases the symptoms of hypoglycemia
Glycodiazine The beta-blocker decreases the symptoms of hypoglycemia
Ibuprofen Risk of inhibition of renal prostaglandins
Indomethacin Risk of inhibition of renal prostaglandins
Insulin The beta-blocker decreases the symptoms of hypoglycemia
Insulin-aspart The beta-blocker decreases the symptoms of hypoglycemia
Insulin-detemir The beta-blocker decreases the symptoms of hypoglycemia
Insulin-glargine The beta-blocker decreases the symptoms of hypoglycemia
Insulin-glulisine The beta-blocker decreases the symptoms of hypoglycemia
Insulin-lispro The beta-blocker decreases the symptoms of hypoglycemia
Isoproterenol Antagonism
Lidocaine The beta-blocker increases the effect and toxicity of lidocaine
Methysergide Ischemia with risk of gangrene
Orciprenaline Antagonism
Pirbuterol Antagonism
Piroxicam Risk of inhibition of renal prostaglandins
Prazosin Risk of hypotension at the beginning of therapy
Procaterol Antagonism
Repaglinide The beta-blocker decreases the symptoms of hypoglycemia
Salbutamol Antagonism
Salmeterol Antagonism
Terbutaline Antagonism
Tolazamide The beta-blocker decreases the symptoms of hypoglycemia
Tolbutamide The beta-blocker decreases the symptoms of hypoglycemia
Verapamil Increased 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.
Pathways
Name SMPDB Link KEGG Link
Atenolol Pathway SMP00298 Link Image
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2D6 (CYP2D6)
Targets
  1. Beta-1 adrenergic receptor
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2D6 (CYP2D6)
Enzyme 1 Gene Name CYP2D6
Enzyme 1 SwissProt ID P10635 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P10635|CP2D6_HUMAN Cytochrome P450 2D6 (EC 1.14.14.1) 
MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVDFQNTPYCFDQ
LRRRFGDVFSLQLAWTPVVVLNGLAAVREALVTHGEDTADRPPVPITQILGFGPRSQGVF
LARYGPAWREQRRFSVSTLRNLGLGKKSLEQWVTEEAACLCAAFANHSGRPFRPNGLLDK
AVSNVIASLTCGRRFEYDDPRFLRLLDLAQEGLKEESGFLREVLNAVPVLLHIPALAGKV
LRFQKAFLTQLDELLTEHRMTWDPAQPPRDLTEAFLAEMEKAKGNPESSFNDENLRIVVA
DLFSAGMVTTSTTLAWGLLLMILHPDVQRRVQQEIDDVIGQVRRPEMGDQAHMPYTTAVI
HEVQRFGDIVPLGMTHMTSRDIEVQGFRIPKGTTLITNLSSVLKDEAVWEKPFRFHPEHF
LDAQGHFVKPEAFLPFSAGRRACLGEPLARMELFLFFTSLLQHFSFSVPTGQPRPSHHGV
FAFLVSPSPYELCAVPR
Drug Target 1 [top]
Target 1 ID 193
Target 1 Name Beta-1 adrenergic receptor
Target 1 Synonyms
  1. Beta-1 adrenoceptor
  2. Beta-1 adrenoreceptor
Target 1 Gene Name ADRB1
Target 1 Protein Sequence >Beta-1 adrenergic receptor 
MGAGVLVLGASEPGNLSSAAPLPDGAATAARLLVPASPPASLLPPASESPEPLSQQWTAG
MGLLMALIVLLIVAGNVLVIVAIAKTPRLQTLTNLFIMSLASADLVMGLLVVPFGATIVV
WGRWEYGSFFCELWTSVDVLCVTASIETLCVIALDRYLAITSPFRYQSLLTRARARGLVC
TVWAISALVSFLPILMHWWRAESDEARRCYNDPKCCDFVTNRAYAIASSVVSFYVPLCIM
AFVYLRVFREAQKQVKKIDSCERRFLGGPARPPSPSPSPVPAPAPPPGPPRPAAAAATAP
LANGRAGKRRPSRLVALREQKALKTLGIIMGVFTLCWLPFFLANVVKAFHRELVPDRLFV
FFNWLGYANSAFNPIIYCRSPDFRKAFQRLLCCARRAARRRHATHGDRPRASGCLARPGP
PPSPGAASDDDDDDVVGATPPARLLEPWAGCNGGAAADSDSSLDEPCRPGFASESKV
Target 1 Number of Residues 484
Target 1 Molecular Weight 51323
Target 1 Theoretical pI 9.03
Target 1 GO Classification
Function
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
amine receptor activity
adrenoceptor activity
beta-adrenergic receptor activity
beta1-adrenergic receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in beta1-adrenergic receptor activity
Target 1 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
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 60-83
  • 97-120
  • 132-155
  • 176-199
  • 222-245
  • 326-349
  • 357-380
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 178200 Link Image
Target 1 UniProtKB/Swiss-Prot ID P08588 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name ADRB1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Cell membrane
  • multi-pass membrane protein. Localized at the plasma membrane. Found in the Golgi upo
Target 1 Gene Sequence >1434 bp 
ATGGGCGCGGGGGTGCTCGTCCTGGGCGCCTCCGAGCCCGGTAACCTGTCGTCGGCCGCA
CCGCTCCCCGACGGCGCGGCCACCGCGGCGCGGCTGCTGGTGCCCGCGTCGCCGCCCGCC
TCGTTGCTGCCTCCCGCCAGCGAAAGCCCCGAGCCGCTGTCTCAGCAGTGGACAGCGGGC
ATGGGTCTGCTGATGGCGCTCATCGTGCTGCTCATCGTGGCGGGCAATGTGCTGGTGATC
GTGGCCATCGCCAAGACGCCGCGGCTGCAGACGCTCACCAACCTCTTCATCATGTCCCTG
GCCAGCGCCGACCTGGTCATGGGGCTGCTGGTGGTGCCGTTCGGGGCCACCATCGTGGTG
TGGGGCCGCTGGGAGTACGGCTCCTTCTTCTGCGAGCTGTGGACCTCAGTGGACGTGCTG
TGCGTGACGGCCAGCATCGAGACCCTGTGTGTCATTGCCCTGGACCGCTACCTCGCCATC
ACCTCGCCCTTCCGCTACCAGAGCCTGCTGACGCGCGCGCGGGCGCGGGGCCTCGTGTGC
ACCGTGTGGGCCATCTCGGCCCTGGTGTCCTTCCTGCCCATCCTCATGCACTGGTGGCGG
GCGGAGAGCGACGAGGCGCGCCGCTGCTACAACGACCCCAAGTGCTGCGACTTCGTCACC
AACCGGGCCTACGCCATCGCCTCGTCCGTAGTCTCCTTCTACGTGCCCCTGTGCATCATG
GCCTTCGTGTACCTGCGGGTGTTCCGCGAGGCCCAGAAGCAGGTGAAGAAGATCGACAGC
TGCGAGCGCCGTTTCCTCGGCGGCCCAGCGCGGCCGCCCTCGCCCTCGCCCTCGCCCGTC
CCCGCGCCCGCGCCGCCGCCCGGACCCCCGCGCCCCGCCGCCGCCGCCGCCACCGCCCCG
CTGGCCAACGGGCGTGCGGGTAAGCGGCGGCCCTCGCGCCTCGTGGCCCTACGCGAGCAG
AAGGCGCTCAAGACGCTGGGCATCATCATGGGCGTCTTCACGCTCTGCTGGCTGCCCTTC
TTCCTGGCCAACGTGGTGAAGGCCTTCCACCGCGAGCTGGTGCCCGACCGCCTCTTCGTC
TTCTTCAACTGGCTGGGCTACGCCAACTCGGCCTTCAACCCCATCATCTACTGCCGCAGC
CCCGACTTCCGCAAGGCCTTCCAGGGACTGCTCTGCTGCGCGCGCAGGGCTGCCCGCCGG
CGCCACGCGACCCACGGAGACCGGCCGCGCGCCTCGGGCTGTCTGGCCCGGCCCGGACCC
CCGCCATCGCCCGGGGCCGCCTCGGACGACGACGACGACGATGTCGTCGGGGCCACGCCG
CCCGCGCGCCTGCTGGAGCCCTGGGCCGGCTGCAACGGCGGGGCGGCGGCGGACAGCGAC
TCGAGCCTGGACGAGCCGTGCCGCCCCGGCTTCGCCTCGGAATCCAAGGTGTAG
Target 1 GenBank Gene ID
Target 1 GeneCard ID ADRB1 Link Image
Target 1 GenAtlas ID ADRB1 Link Image
Target 1 HGNC ID HGNC:285 Link Image
Target 1 Chromosome Location 10
Target 1 Locus 10q24-q26
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Mason DA, Moore JD, Green SA, Liggett SB: A gain-of-function polymorphism in a G-protein coupling domain of the human beta1-adrenergic receptor. J Biol Chem. 1999 Apr 30;274(18):12670-4. [PubMed Link Image]
  2. Moore JD, Mason DA, Green SA, Hsu J, Liggett SB: Racial differences in the frequencies of cardiac beta(1)-adrenergic receptor polymorphisms: analysis of c145A>G and c1165G>C. Hum Mutat. 1999 Sep 19;14(3):271. [PubMed Link Image]
  3. Borjesson M, Magnusson Y, Hjalmarson A, Andersson B: A novel polymorphism in the gene coding for the beta(1)-adrenergic receptor associated with survival in patients with heart failure. Eur Heart J. 2000 Nov;21(22):1853-8. [PubMed Link Image]
  4. Ranade K, Jorgenson E, Sheu WH, Pei D, Hsiung CA, Chiang FT, Chen YD, Pratt R, Olshen RA, Curb D, Cox DR, Botstein D, Risch N: A polymorphism in the beta1 adrenergic receptor is associated with resting heart rate. Am J Hum Genet. 2002 Apr;70(4):935-42. Epub 2002 Feb 18. [PubMed Link Image]
  5. Frielle T, Collins S, Daniel KW, Caron MG, Lefkowitz RJ, Kobilka BK: Cloning of the cDNA for the human beta 1-adrenergic receptor. Proc Natl Acad Sci U S A. 1987 Nov;84(22):7920-4. [PubMed Link Image]
Target 1 Drug 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 Link Image]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]

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.