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Showing toxin card for Atenolol (T3D3480)

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Version 1.0
Creation Date 2009-07-30 17:58:38
Update Date 2010-05-18 21:03:41
Accession Number T3D3480
Name Atenolol
Compound Type
  • Adrenergic Agent
  • Adrenergic beta-Antagonist
  • Anti-Arrhythmia Agent
  • Anti-Arrhythmic Agent
  • Antihypertensive Agent
  • Drug
  • Sympatholytic
Description A cardioselective beta-adrenergic blocker possessing properties and potency similar to propranolol, but without a negative inotropic effect. [PubChem]
Synonyms
  1. (+-)-4-(2-Hydroxy-3-isopropylaminopropoxy)phenylacetamide
  2. (+-)-atenolol
  3. 1-p-Carbamoylmethylphenoxy-3-isopropylamino-2-propanol
  4. 2-(4-(2-Hydroxy-3-isopropylaminopropoxy)phenyl)acetamid
  5. 2-(4-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl)acetamide
  6. 2-(p-(2-Hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide
  7. 4-[2 -Hydroxy-3 -(isopropylamino)-propoxy]phenylacetamide
  8. 4-[2'-Hydroxy-3'-(isopropylamino)propoxy]phenylacetamide
  9. Acetamide,2-(p-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)
  10. Aircrit
  11. Alinor
  12. Altol
  13. Anselol
  14. Antipressan
  15. Apo-Atenol Tab
  16. Apo-atenolol
  17. Atcardil
  18. Atecard
  19. Atehexal
  20. Atenblock
  21. Atendol
  22. Atenet
  23. Ateni
  24. Atenil
  25. Atenol
  26. Atenol 1A pharma
  27. Atenol CT
  28. Atenol GNR
  29. Atenol MSD
  30. Atenol NM pharma
  31. Atenol PB
  32. Atenol acis
  33. Atenol al
  34. Atenol atid
  35. Atenol cophar
  36. Atenol fecofar
  37. Atenol gador
  38. Atenol genericon
  39. Atenol heumann
  40. Atenol nordic
  41. Atenol quesada
  42. Atenol stada
  43. Atenol tika
  44. Atenol trom
  45. Atenol von CT
  46. Atenol-mepha
  47. Atenol-ratiopharm
  48. Atenol-wolff
  49. Atenolin
  50. Atenolol (JP15/USP/INN)
  51. Atenolol (jan/usp)
  52. Atenolol [usan:ban:inn:jan]
  53. Atenolol [usan:inn:ban:jan]
  54. Atenolol and chlorthalidone
  55. Atenolol-100 Tab
  56. Atenololum
  57. Atenololum [inn-latin]
  58. Atenomel
  59. Atereal
  60. Aterol
  61. Bci atenolol
  62. Betablok
  63. Betacard
  64. Betasyn
  65. Betatop ge
  66. Blocotenol
  67. Blokium
  68. Cardaxen
  69. Cardiopress
  70. Co atenolol
  71. Corotenol
  72. Cuxanorm
  73. Dom-Atenolol
  74. Duraatenolol
  75. Duratenol
  76. Evitocor
  77. Farnormin
  78. Felo-bits
  79. Gen-Atenolol
  80. Hipres
  81. Hypoten
  82. Ibinolo
  83. Internolol
  84. Jenatenol
  85. Juvental
  86. Lo-ten
  87. Lontermin
  88. Loten
  89. Lotenal
  90. Med Atenolol
  91. Myocord
  92. Neatenol
  93. Normalol
  94. Normiten
  95. Noten
  96. Novo-Atenol
  97. Novo-atenol
  98. Nu-Atenol
  99. Oraday
  100. Ormidol
  101. PHL-atenolol
  102. PMS-atenolol
  103. Panapres
  104. Plenacor
  105. Premorine
  106. Prenolol
  107. Prenormine
  108. Prinorm
  109. Procaterol hydrochloride
  110. Ran-atenolol
  111. Ratio-atenolol
  112. Riva-Atenolol
  113. Riva-atenolol
  114. Sandoz atenolol
  115. Scheinpharm atenol
  116. Seles beta
  117. Selobloc
  118. Serten
  119. Servitenol
  120. Stermin
  121. TENORETIC 100
  122. TENORETIC 50
  123. Tenidon
  124. Teno-basan
  125. Tenobloc
  126. Tenoblock
  127. Tenolol
  128. Tenoprin
  129. Tenoretic
  130. Tenormin
  131. Tenormin (TN)
  132. Tenormin
  133. Tenormine
  134. Tenormine [french]
  135. Tensimin
  136. Tensotin
  137. Tredol
  138. Unibloc
  139. Uniloc
  140. Vascoten
  141. Vericordin
  142. Wesipin
  143. Xaten
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=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)
InChI Key InChIKey=METKIMKYRPQLGS-UHFFFAOYSA-N
PubChem Compound ID 2249 Link Image
KEGG ID C13235 Link Image
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID Not Available
BioCyc ID Not Available
SuperToxic ID Not Available
CTD ID Not Available
Stitch ID Atenolol Link Image
DrugBank ID DB00335 Link Image
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Atenolol Link Image
Monoisotopic Mass 266.163043
MOL File Show
PDB File Show
SDF File Show
SMILES CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1
Appearance Not Available
Melting Point 146-148oC
Solubility 13.5 mg/mL
Predicted LogP 0.425
Route of Exposure Oral
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.
Metabolism Hepatic (minimal)
Toxicity Values LD50: 2000-3000 mg/kg(oral, mice).
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Not Available
Minimum Risk Level Not Available
Health Effects Not Available
Symptoms Symptoms of an atenolol overdose include a slow heart beat, shortness of breath, fainting, dizziness, weakness, confusion, nausea, and vomiting.
Treatment Not Available
General References
  • V508 - Drugs.com
Targets
  1. Beta-1 adrenergic receptor
Target 1 [top]
Target 1 ID 1175
Target 1 Name Beta-1 adrenergic receptor
Target 1 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.
Target 1 Description 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 Synonyms
  1. Beta-1 adrenoreceptor; Beta-1 adrenoceptor
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 477
Target 1 Molecular Weight 51322.1
Target 1 Theoretical pI 9.03
Target 1 GO Classification
Function
amine receptor activity
adrenoceptor activity
beta-adrenergic receptor activity
beta1-adrenergic receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like 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 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 56-84
  • 94-120
  • 133-154
  • 173-196
  • 223-248
  • 320-349
  • 355-377
Target 1 Essentiality Non Essential
Target 1 Domain Function PF00001:7tm_1
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB ID P08588 Link Image
Target 1 Cellular Location Cell membrane
Target 1 Gene Sequence >1434 bp 
CCCCGGCCTCCGCAGCTCGGCATGGGCGCGGGGGTGCTCGTCCTGGGCGCCTCCGAGCCC
GGTAACCTGTCGTCGGCCGCACCGCTCCCCGACGGCGCGGCCACCGCGGCGCGGCTGCTG
GTGCCCGCGTCGCCGCCCGCCTCGTTGCTGCCTCCCGCCAGCGAAAGCCCCGAGCCGCTG
TCTCAGCAGTGGACAGCGGGCATGGGTCTGCTGATGGCGCTCATCGTGCTGCTCATCGTG
GCGGGCAATGTGCTGGTGATCGTGGCCATCGCCAAGACGCCGCGGCTGCAGACGCTCACC
AACCTCTTCATCATGTCCCTGGCCAGCGCCGACCTGGTCATGGGGCTGCTGGTGGTGCCG
TTCGGGGCCACCATCGTGGTGTGGGGCCGCTGGGAGTACGGCTCCTTCTTCTGCGAGCTG
TGGACCTCAGTGGACGTGCTGTGCGTGACGGCCAGCATCGAGACCCTGTGTGTCATTGCC
CTGGACCGCTACCTCGCCATCACCTCGCCCTTCCGCTACCAGAGCCTGCTGACGCGCGCG
CGGGCGCGGGGCCTCGTGTGCACCGTGTGGGCCATCTCGGCCCTGGTGTCCTTCCTGCCC
ATCCTCATGCACTGGTGGCGGGCGGAGAGCGACGAGGCGCGCCGCTGCTACAACGACCCC
AAGTGCTGCGACTTCGTCACCAACCGGGCCTACGCCATCGCCTCGTCCGTAGTCTCCTTC
TACGTGCCCCTGTGCATCATGGCCTTCGTGTACCTGCGGGTGTTCCGCGAGGCCCAGAAG
CAGGTGAAGAAGATCGACAGCTGCGAGCGCCGTTTCCTCGGCGGCCCAGCGCGGCCGCCC
TCGCCCTCGCCCTCGCCCGTCCCCGCGCCCGCGCCGCCGCCCGGACCCCCGCGCCCCGCC
GCCGCCGCCGCCACCGCCCCGCTGGCCAACGGGCGTGCGGGTAAGCGGCGGCCCTCGCGC
CTCGTGGCCCTACGCGAGCAGAAGGCGCTCAAGACGCTGGGCATCATCATGGGCGTCTTC
ACGCTCTGCTGGCTGCCCTTCTTCCTGGCCAACGTGGTGAAGGCCTTCCACCGCGAGCTG
GTGCCCGACCGCCTCTTCGTCTTCTTCAACTGGCTGGGCTACGCCAACTCGGCCTTCAAC
CCCATCATCTACTGCCGCAGCCCCGACTTCCGCAAGGCCTTCCAGGGACTGCTCTGCTGC
GCGCGCAGGGCTGCCCGCCGGCGCCACGCGACCCACGGAGACCGGCCGCGCGCCTCGGGC
TGTCTGGCCCGGCCCGGACCCCCGCCATCGCCCGGGGCCGCCTCGGACGACGACGACGAC
GATGTCGTCGGGGCCACGCCGCCCGCGCGCCTGCTGGAGCCCTGGGCCGGCTGCAACGGC
GGGGCGGCGGCGGACAGCGACTCGAGCCTGGACGAGCCGTGCCGCCCCGGCTTC
Target 1 GenBank Gene ID Not Available
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 Chromosome:10
Target 1 Locus 10q24-q26
Target 1 SNPs SNPJam Report Link Image
Target 1 Toxin References
  • S918 - Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]
  • V510 - 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]
  • V509 - 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]
  • V512 - 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]
  • V511 - 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]
Target 1 General References 2825170; 10477438; 15164054; 15358775; 10212248; 11052857; 11854867

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