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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-18 09:02:16 UTC
Update Date2017-10-23 19:03:55 UTC
HMDB IDHMDB0001937
Secondary Accession Numbers
  • HMDB01937
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
Structure
Thumb
Synonyms
ValueSource
ProventilChEBI
(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
AlbuterolHMDB
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
2-t-butylamino-1-(4-Hydroxy-3-hydroxy-3-hydroxymethyl)phenylethanolMeSH
Albuterol sulfateMeSH
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
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
  • Phenol
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Tissue and substructures:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point157 - 158 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.15 g/LNot Available
LogP1.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.15 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.87 m³·mol⁻¹ChemAxon
Polarizability26.86 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ff9-9710000000-a986fa7cee66bc21b185View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0535-4494200000-4d44fc69fd47c8bde941View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-002b-0900000000-1c9889f5fc33443c7b3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0090000000-afe3df5bdead805eacafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-1d8b235dd1e02960dba1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00dr-0090000000-6fee6c25dfbf9c3a7c13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0290000000-0d38029df88ee8018d9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00kf-0950000000-9572451e9f596ae94494View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-05c59c5c9d63de269febView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-8ef6b84074e243e637bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00dr-0090000000-e288fafc6755fa4abcbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0290000000-5569e08c145733118852View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0296-0940000000-f3558c829fecc8fea6f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0900000000-9b7ad78396782fd2237dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0090000000-19973e6238f364b40ec6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dl-0190000000-bec72774da692a955281View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-9d1b7a0e974ab4c5c2cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0090000000-98cef35812448be3e2dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-006x-0090000000-182d7b602151e8ac7849View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-006t-0950000000-935c99cfc4690ce298f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-064806e46a30b7dd760bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-63e55815a4526e7feb52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4j-1890000000-a1d656ba6a83af80a632View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avj-4910000000-dbdf8585f040436bd841View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-1190000000-2bd296e3b89e66c9df27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-4690000000-2cc3920d36cafabbfe05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9800000000-f42f6ecf60fdf4f504ffView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Smooth Muscle
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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
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 (1985). 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