albuterol (CHEBI:2549)

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ChEBI Name	albuterol

ChEBI ID	CHEBI:2549

Definition	A member of the class of phenylethanolamines that is 4-(2-amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol having a tert-butyl group attached to the nirogen atom. It acts as a β-adrenergic agonist used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB52675641, ChemicalBook:CB84796992, ChemicalBook:CB3129524, eMolecules:26756445, eMolecules:511751

Download	Molfile XML SDF

Wikipedia	License
Salbutamol, also known as albuterol and sold under the brand name Ventolin among others, is a medication that opens up the medium and large airways in the lungs. It is a short-acting β2 adrenergic receptor agonist that causes relaxation of airway smooth muscle. It is used to treat asthma, including asthma attacks and exercise-induced bronchoconstriction, as well as chronic obstructive pulmonary disease (COPD). It may also be used to treat high blood potassium levels. Salbutamol is usually used with an inhaler or nebulizer, but it is also available in a pill, liquid, and intravenous solution. Onset of action of the inhaled version is typically within 15 minutes and lasts for two to six hours. Common side effects include shakiness, headache, fast heart rate, dizziness, and feeling anxious. Serious side effects may include worsening bronchospasm, irregular heartbeat, and low blood potassium levels. It can be used during pregnancy and breastfeeding, but safety is not entirely clear. Salbutamol was patented in 1966 in Britain and became commercially available in the UK in 1969. It was approved for medical use in the United States in 1982. It is on the World Health Organization's List of Essential Medicines. Salbutamol is available as a generic medication. In 2022, it was the seventh most commonly prescribed medication in the United States, with more than 59 million prescriptions.
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Formula

C13H21NO3

Net Charge

Average Mass

239.31070

Monoisotopic Mass

239.15214

InChI

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

InChIKey

NDAUXUAQIAJITI-UHFFFAOYSA-N

SMILES

CC(C)(C)NCC(O)c1ccc(O)c(CO)c1

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects. Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	beta-adrenergic agonist An agent that selectively binds to and activates beta-adrenergic receptors. xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.

Application(s):	beta-adrenergic agonist An agent that selectively binds to and activates beta-adrenergic receptors. bronchodilator agent An agent that causes an increase in the expansion of a bronchus or bronchial tubes.

ChEBI Ontology
Outgoing	albuterol (CHEBI:2549) has role β-adrenergic agonist (CHEBI:35522) albuterol (CHEBI:2549) has role bronchodilator agent (CHEBI:35523) albuterol (CHEBI:2549) has role environmental contaminant (CHEBI:78298) albuterol (CHEBI:2549) has role xenobiotic (CHEBI:35703) albuterol (CHEBI:2549) is a phenols (CHEBI:33853) albuterol (CHEBI:2549) is a phenylethanolamines (CHEBI:25990) albuterol (CHEBI:2549) is a secondary amino compound (CHEBI:50995)

Incoming	albuterol sulfate (CHEBI:2550) has functional parent albuterol (CHEBI:2549) (R)-salbutamol (CHEBI:8746) is a albuterol (CHEBI:2549)

IUPAC Name

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

Citations

Last Modified

22 February 2017