ContaminantDB: Salbutamol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:14:00 UTC

Update Date

2016-11-09 01:09:11 UTC

Accession Number

CHEM003692

Identification

Common Name

Salbutamol

Class

Small Molecule

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.

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Adrenergic beta-2 Receptor Agonist
Amine
Bronchodilator Agent
Drug
Food Toxin
Organic Compound
Synthetic Compound
Tocolytic Agent

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Proventil	ChEBI
(L)-Albuterol	HMDB
1-(Tert-butylaminomethyl)-4-hydroxy-m-xylene-alpha1,alpha3-diol	HMDB
2-(Tert-butylamino)-1-(4-hydroxy-3-hydroxymethylphenyl)ethanol	HMDB
4-Hydroxy-3-hydroxymethyl-alpha-((tert-butylamino)methyl)benzyl alcohol	HMDB
Aerolin	HMDB
Albuterol	HMDB
Almotex	HMDB
Alpha'-((tert-butylamino)methyl)-4-hydroxy-m-xylene-alpha,alpha'-diol	HMDB
Alti-salbutamol	HMDB
Anebron	HMDB
Arubendol-salbutamol	HMDB
Asmadil	HMDB
Asmanil	HMDB
Asmasal	HMDB
Asmatol	HMDB
Asmaven	HMDB
Asmidon	HMDB
Asmol	HMDB
Asmol uni-dose	HMDB
Asthalin	HMDB
Broncho-spray	HMDB
Broncovaleas	HMDB
Bronter	HMDB
Bugonol	HMDB
Bumol	HMDB
Butamol	HMDB
Buto-asma	HMDB
Butohaler	HMDB
Butotal	HMDB
Butovent	HMDB
Buventol	HMDB
Cobutolin	HMDB
Dilatamol	HMDB
DL-Albuterol	HMDB
DL-N-Tert-butyl-2-(4-hydroxy-3-hydroxymethylphenyl)-2-hydroxyethylamine	HMDB
DL-Salbutamol	HMDB
Farcolin	HMDB
Gerivent	HMDB
Grafalin	HMDB
Levalbuterol	HMDB
Libretin	HMDB
Medolin	HMDB
Mozal	HMDB
Novosalmol	HMDB
Parasma	HMDB
Pneumolat	HMDB
Proventil hfa	HMDB
Proventil inhaler	HMDB
R-Salbutamol	HMDB
Respax	HMDB
Respolin	HMDB
Sabutal	HMDB
Salamol	HMDB
Salbetol	HMDB
Salbron	HMDB
Salbu-basf	HMDB
Salbu-fatol	HMDB
Salbuhexal	HMDB
Salbulin	HMDB
Salbupur	HMDB
Salbusian	HMDB
Salbutalan	HMDB
Salbutamol free base	HMDB
Salbutamol sulfate	HMDB
Salbutamol sulphate	HMDB
Salbutamolum	HMDB
Salbutan	HMDB
Salbutol	HMDB
Salbuven	HMDB
Salbuvent	HMDB
Sallbupp	HMDB
Salmaplon	HMDB
Salomol	HMDB
Salvent	HMDB
Saventol	HMDB
Servitamol	HMDB
Spreor	HMDB
Sultanol	HMDB
Sultanol N	HMDB
Suprasma	HMDB
Suxar	HMDB
Theosal	HMDB
Tobybron	HMDB
Vencronyl	HMDB
Ventamol	HMDB
Ventilan	HMDB
Ventiloboi	HMDB
Ventodisks	HMDB
Ventolin	HMDB
Ventolin inhaler	HMDB
Ventolin rotacaps	HMDB
Ventoline	HMDB
Volare albuterol hfa	HMDB
Volare easi-breathe	HMDB
Volmax	HMDB
Zaperin	HMDB
2-t-Butylamino-1-(4-hydroxy-3-hydroxy-3-hydroxymethyl)phenylethanol	HMDB
Albuterol sulfate	HMDB

Chemical Formula

C₁₃H₂₁NO₃

Average Molecular Mass

239.311 g/mol

Monoisotopic Mass

239.152 g/mol

CAS Registry Number

18559-94-9

IUPAC Name

4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol

Traditional Name

salbutamol

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

Description

belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyl alcohols

Direct Parent

Benzyl 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylethanolamines (CHEBI:2549 )
phenols (CHEBI:2549 )
secondary amino compound (CHEBI:2549 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	147-149°C
Boiling Point	Not Available
Solubility	1.41E+004 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	2.15 g/L	ALOGPS
logP	0.44	ALOGPS
logP	0.34	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	10.12	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.87 m³·mol⁻¹	ChemAxon
Polarizability	26.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ff9-9710000000-a986fa7cee66bc21b185	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0535-4494200000-4d44fc69fd47c8bde941	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-002b-0900000000-1c9889f5fc33443c7b3b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00di-0090000000-afe3df5bdead805eacaf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0090000000-1d8b235dd1e02960dba1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00dr-0090000000-6fee6c25dfbf9c3a7c13	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0290000000-0d38029df88ee8018d9a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00kf-0950000000-9572451e9f596ae94494	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0006-0900000000-05c59c5c9d63de269feb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0090000000-8ef6b84074e243e637bd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00dr-0090000000-e288fafc6755fa4abcba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0290000000-5569e08c145733118852	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0296-0940000000-f3558c829fecc8fea6f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0006-0900000000-9b7ad78396782fd2237d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00di-0090000000-19973e6238f364b40ec6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00dl-0190000000-bec72774da692a955281	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0900000000-9d1b7a0e974ab4c5c2cf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-0090000000-98cef35812448be3e2db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-006x-0090000000-182d7b602151e8ac7849	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-006t-0950000000-935c99cfc4690ce298f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-064806e46a30b7dd760b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0190000000-63e55815a4526e7feb52	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0g4j-1890000000-a1d656ba6a83af80a632	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0avj-4910000000-dbdf8585f040436bd841	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0079-1190000000-2bd296e3b89e66c9df27	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-4690000000-2cc3920d36cafabbfe05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9800000000-f42f6ecf60fdf4f504ff	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Systemic absorption is rapid following aerosol administration.

Mechanism of Toxicity

Salbutamol is a beta(2)-adrenergic agonist and thus it stimulates beta(2)-adrenergic receptors. Binding of albuterol to beta(2)-receptors in the lungs results in relaxation of bronchial smooth muscles. It is believed that salbutamol increases cAMP production by activating adenylate cyclase, and the actions of salbutamol are mediated by cAMP. Increased intracellular cyclic AMP increases the activity of cAMP-dependent protein kinase A, which inhibits the phosphorylation of myosin and lowers intracellular calcium concentrations. A lowered intracellular calcium concentration leads to a smooth muscle relaxation and bronchodilation. In addition to bronchodilation, salbutamol inhibits the release of bronchoconstricting agents from mast cells, inhibits microvascular leakage, and enhances mucociliary clearance.

Metabolism

Hydrolyzed by esterases in tissue and blood to the active compound colterol. The drug is also conjugatively metabolized to salbutamol 4'-O-sulfate. Route of Elimination: Approximately 72% of the inhaled dose is excreted in the urine within 24 hours, 28% as unchanged drug and 44% as metabolite. Half Life: 1.6 hours

Toxicity Values

LD₅₀=1100 mg/kg (orally in mice)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For symptomatic relief and prevention of bronchospasm due to bronchial asthma, chronic bronchitis, and other chronic bronchopulmonary disorders such as COPD.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01001

HMDB ID

HMDB0001937

FooDB ID

FDB022752

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

799

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Toshikuni Kawazi, Masahiro Ono, Nobuko Inoue, “Salbutamol-containing plaster and method of producing same.” U.S. Patent US5068103, issued February, 1984.

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=8267204

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=9847435

3. 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.

4. 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.

Salbutamol (CHEM003692)

Structure for CHEM003692: Salbutamol