You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-05-18 09:02:16 UTC
Update Date2014-09-23 05:28:01 UTC
HMDB IDHMDB01937
Secondary Accession NumbersNone
Metabolite Identification
Common NameSalbutamol
DescriptionSalbutamol 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
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 sulfate
  67. Salbutamol sulphate
  68. Salbutamolum
  69. Salbutan
  70. Salbutol
  71. Salbuven
  72. Salbuvent
  73. Sallbupp
  74. Salmaplon
  75. Salomol
  76. Salvent
  77. Saventol
  78. Servitamol
  79. Spreor
  80. Sultanol
  81. Sultanol N
  82. Suprasma
  83. Suxar
  84. Theosal
  85. Tobybron
  86. Vencronyl
  87. Ventamol
  88. Ventilan
  89. Ventiloboi
  90. Ventodisks
  91. Ventolin
  92. Ventolin inhaler
  93. Ventolin rotacaps
  94. Ventoline
  95. Volare albuterol hfa
  96. Volare easi-breathe
  97. Volmax
  98. Zaperin
Chemical FormulaC13H21NO3
Average Molecular Weight239.3107
Monoisotopic Molecular Weight239.152143543
IUPAC Name4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
Traditional Namesalbutamol
CAS Registry Number18559-94-9
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 KeyNDAUXUAQIAJITI-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenethylamines
Sub ClassN/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 ParentPhenethylamines
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point157 - 158 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.15e+00 g/LNot Available
LogP1.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.15ALOGPS
logP0.44ALOGPS
logP0.34ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)10.12ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.87 m3·mol-1ChemAxon
Polarizability26.96 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Smooth Muscle
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-4 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01001
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022752
KNApSAcK IDNot Available
Chemspider ID1999
KEGG Compound IDC11770
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSalbutamol
NuGOwiki LinkHMDB01937
Metagene LinkHMDB01937
METLIN ID799
PubChem Compound123600
PDB ID68H
ChEBI ID8746
References
Synthesis ReferenceNot 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
  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

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
General function:
Involved in cytokine activity
Specific function:
IL-8 is a chemotactic factor that attracts neutrophils, basophils, and T-cells, but not monocytes. It is also involved in neutrophil activation. It is released from several cell types in response to an inflammatory stimulus. IL-8(6-77) has a 5-10-fold higher activity on neutrophil activation, IL-8(5-77) has increased activity on neutrophil activation and IL-8(7-77) has a higher affinity to receptors CXCR1 and CXCR2 as compared to IL-8(1-77), respectively
Gene Name:
IL8
Uniprot ID:
P10145
Molecular weight:
11098.0