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Record Information
Version3.6
Creation Date2006-05-18 09:02:16 UTC
Update Date2016-02-11 01:05:07 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
ValueSource
ProventilChEBI
SalbutamolChEBI
(L)-AlbuterolHMDB
1-(Tert-butylaminomethyl)-4-hydroxy-m-xylene-alpha1,alpha3-diolHMDB
2-(Tert-butylamino)-1-(4-hydroxy-3-hydroxymethylphenyl)ethanolHMDB
4-Hydroxy-3-hydroxymethyl-alpha-((tert-butylamino)methyl)benzyl alcoholHMDB
AerolinHMDB
AlmotexHMDB
Alpha'-((tert-butylamino)methyl)-4-hydroxy-m-xylene-alpha,alpha'-diolHMDB
Alti-salbutamolHMDB
AnebronHMDB
Arubendol-salbutamolHMDB
AsmadilHMDB
AsmanilHMDB
AsmasalHMDB
AsmatolHMDB
AsmavenHMDB
AsmidonHMDB
AsmolHMDB
Asmol uni-doseHMDB
AsthalinHMDB
broncho-SprayHMDB
BroncovaleasHMDB
BronterHMDB
BugonolHMDB
BumolHMDB
ButamolHMDB
buto-AsmaHMDB
ButohalerHMDB
ButotalHMDB
ButoventHMDB
BuventolHMDB
CobutolinHMDB
DilatamolHMDB
DL-AlbuterolHMDB
DL-N-Tert-butyl-2-(4-hydroxy-3-hydroxymethylphenyl)-2-hydroxyethylamineHMDB
DL-SalbutamolHMDB
FarcolinHMDB
GeriventHMDB
GrafalinHMDB
LevalbuterolHMDB
LibretinHMDB
MedolinHMDB
MozalHMDB
NovosalmolHMDB
ParasmaHMDB
PneumolatHMDB
Proventil hfaHMDB
Proventil inhalerHMDB
R-SalbutamolHMDB
RespaxHMDB
RespolinHMDB
SabutalHMDB
SalamolHMDB
SalbetolHMDB
SalbronHMDB
Salbu-basfHMDB
Salbu-fatolHMDB
SalbuhexalHMDB
SalbulinHMDB
SalbupurHMDB
SalbusianHMDB
SalbutalanHMDB
Salbutamol free baseHMDB
Salbutamol sulfateHMDB
Salbutamol sulphateHMDB
SalbutamolumHMDB
SalbutanHMDB
SalbutolHMDB
SalbuvenHMDB
SalbuventHMDB
SallbuppHMDB
SalmaplonHMDB
SalomolHMDB
SalventHMDB
SaventolHMDB
ServitamolHMDB
SpreorHMDB
SultanolHMDB
Sultanol NHMDB
SuprasmaHMDB
SuxarHMDB
TheosalHMDB
TobybronHMDB
VencronylHMDB
VentamolHMDB
VentilanHMDB
VentiloboiHMDB
VentodisksHMDB
VentolinHMDB
Ventolin inhalerHMDB
Ventolin rotacapsHMDB
VentolineHMDB
Volare albuterol hfaHMDB
Volare easi-breatheHMDB
VolmaxHMDB
ZaperinHMDB
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 KeyInChIKey=NDAUXUAQIAJITI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl alcohols
Direct ParentBenzyl alcohols
Alternative Parents
Substituents
  • Benzyl alcohol
  • Aralkylamine
  • Phenol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but 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 Solubility2.15 mg/mLALOGPS
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
Polarizability26.86 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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. [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. [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