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Human Metabolome Database Version 3.5

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Showing metabocard for Salbutamol (HMDB01937)

Record Information
Version 3.5
Creation Date 2006-05-18 03:02:16 -0600
Update Date 2013-05-15 15:17:19 -0600
HMDB ID HMDB01937
Secondary Accession Numbers None
Metabolite Identification
Common Name Salbutamol
Description Salbutamol is a short-acting, selective beta2-adrenergic receptor agonist used in the treatment of asthma and COPD. It is 29 times more selective for beta2 receptors than beta1 receptors giving it higher specificity for pulmonary beta receptors versus beta1-adrenergic receptors located in the heart. Salbutamol is formulated as a racemic mixture of the R- and S-isomers. The R-isomer has 150 times greater affinity for the beta2-receptor than the S-isomer and the S-isomer has been associated with toxicity. This lead to the development of levalbuterol, the single R-isomer of salbutamol. However, the high cost of levalbuterol compared to salbutamol has deterred wide-spread use of this enantiomerically pure version of the drug. Salbutamol is generally used for acute episodes of bronchospasm caused by bronchial asthma, chronic bronchitis and other chronic bronchopulmonary disorders such as chronic obstructive pulmonary disorder (COPD). It is also used prophylactically for exercise-induced asthma. Salbutamol or albuterol is a short-acting beta 2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma. -- Pubchem.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (L)-albuterol
  2. 1-(Tert-butylaminomethyl)-4-hydroxy-m-xylene-alpha1,alpha3-diol
  3. 2-(Tert-butylamino)-1-(4-hydroxy-3-hydroxymethylphenyl)ethanol
  4. 4-Hydroxy-3-hydroxymethyl-alpha-((tert-butylamino)methyl)benzyl alcohol
  5. Aerolin
  6. Albuterol
  7. Almotex
  8. alpha'-((Tert-butylamino)methyl)-4-hydroxy-m-xylene-alpha,alpha'-diol
  9. alpha(Sup 1)-((tert-butylamino)methyl)-4-hydroxy-m-xylene-alpha,alpha'-diol
  10. Alti-salbutamol
  11. Anebron
  12. Arubendol-salbutamol
  13. Asmadil
  14. Asmanil
  15. Asmasal
  16. Asmatol
  17. Asmaven
  18. Asmidon
  19. Asmol
  20. Asmol uni-dose
  21. Asthalin
  22. Broncho-spray
  23. Broncovaleas
  24. Bronter
  25. Bugonol
  26. Bumol
  27. Butamol
  28. Buto-asma
  29. Butohaler
  30. Butotal
  31. Butovent
  32. Buventol
  33. Cobutolin
  34. Dilatamol
  35. DL-albuterol
  36. DL-N-tert-butyl-2-(4-hydroxy-3-hydroxymethylphenyl)-2-hydroxyethylamine
  37. DL-salbutamol
  38. Farcolin
  39. Gerivent
  40. Grafalin
  41. Levalbuterol
  42. Libretin
  43. Medolin
  44. Mozal
  45. Novosalmol
  46. Parasma
  47. Pneumolat
  48. Proventil
  49. Proventil hfa
  50. Proventil inhaler
  51. R-Salbutamol
  52. Respax
  53. Respolin
  54. Sabutal
  55. Salamol
  56. Salbetol
  57. Salbron
  58. Salbu-basf
  59. Salbu-fatol
  60. Salbuhexal
  61. Salbulin
  62. Salbupur
  63. Salbusian
  64. Salbutalan
  65. Salbutamol free base
  66. Salbutamol sulphate
  67. Salbutamolum
  68. Salbutan
  69. Salbutol
  70. Salbuven
  71. Salbuvent
  72. Sallbupp
  73. Salmaplon
  74. Salomol
  75. Salvent
  76. Saventol
  77. Servitamol
  78. Spreor
  79. Sultanol
  80. Sultanol N
  81. Suprasma
  82. Suxar
  83. Theosal
  84. Tobybron
  85. Vencronyl
  86. Ventamol
  87. Ventilan
  88. Ventiloboi
  89. Ventodisks
  90. Ventolin
  91. Ventolin inhaler
  92. Ventolin rotacaps
  93. Ventoline
  94. Volare albuterol hfa
  95. Volare easi-breathe
  96. Volmax
  97. Zaperin
Chemical Formula C13H21NO3
Average Molecular Weight 239.3107
Monoisotopic Molecular Weight 239.152143543
IUPAC Name 4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
Traditional IUPAC Name salbutamol
CAS Registry Number 18559-94-9
SMILES CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1
InChI Identifier InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3
InChI Key NDAUXUAQIAJITI-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenethylamines
Sub Class N/A
Other Descriptors
  • Organic Compounds
  • phenylethanolamines(ChEBI)
  • secondary amine(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • Benzyl Alcohol Derivative
  • Phenol
  • Phenol Derivative
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct Parent Phenethylamines
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 157 - 158 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 2.15e+00 g/L Not Available
LogP 1.4 Not Available
Predicted Properties
Property Value Source
Water Solubility 2.15 g/L ALOGPS
LogP 0.44 ALOGPS
LogP 0.34 ChemAxon
LogS -2.05 ALOGPS
pKa (strongest acidic) 10.12 ChemAxon
pKa (strongest basic) 9.4 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 72.72 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 67.87 ChemAxon
Polarizability 26.96 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location
  • Smooth Muscle
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01001 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022752
KNApSAcK ID Not Available
Chemspider ID 1999 Link_out
KEGG Compound ID C11770 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Salbutamol Link_out
NuGOwiki Link HMDB01937 Link_out
Metagene Link HMDB01937 Link_out
METLIN ID 799 Link_out
PubChem Compound 123600 Link_out
PDB ID 68H Link_out
ChEBI ID 8746 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Fayon M, Dumas De La Roque E, Berger P, Begueret H, Ousova O, Molimard M, Marthan R: Increased relaxation of immature airways to beta2-adrenoceptor agonists is related to attenuated expression of postjunctional smooth muscle muscarinic M2 receptors. J Appl Physiol. 2005 Apr;98(4):1526-33. Epub 2004 Dec 3. Pubmed: 15579574 Link_out
  2. Yoshihara S, Yamada Y, Abe T, Kashimoto K, Linden A, Arisaka O: Long-lasting smooth-muscle relaxation by a novel PACAP analogue in human bronchi. Regul Pept. 2004 Dec 15;123(1-3):161-5. Pubmed: 15518907 Link_out
Enzymes
Name: Beta-2 adrenergic receptor
Reactions:
    Gene Name: ADRB2
    Uniprot ID: P07550 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Interleukin-8
    Reactions:
      Gene Name: IL8
      Uniprot ID: P10145 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA