salbutamol   Click here for help

GtoPdb Ligand ID: 558

Synonyms: albuterol | SCH-13949W | Ventolin®
Approved drug Immunopharmacology Ligand
salbutamol is an approved drug (FDA (1981))
Compound class: Synthetic organic
Comment: The approved drug salbutamol is a racemic mixture of two enantiomers: levosalbutamol ((R)-salbutamol) and (S)-salbutamol. The structure shown here does not specify stereochemistry and represents the mixture. The US FDA approved this drug with the name albuterol.
Marketed formulations may contain salbutamol sulfate (PubChem CID 9884233).
Salbutamol is termed a 'short-acting beta-agonist' (SABA).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 4
Rotatable bonds 5
Topological polar surface area 72.72
Molecular weight 239.15
XLogP 1.44
No. Lipinski's rules broken 0
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Canonical SMILES OCc1cc(ccc1O)C(CNC(C)(C)C)O
Isomeric SMILES OCc1cc(ccc1O)C(CNC(C)(C)C)O
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
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Summary of Clinical Use Click here for help
Highly selective β2-adrenoceptor agonist used in the treatment of COPD and asthma.
In April 2015, the FDA expanded approval to include treatment or prevention of bronchospasm in patients with reversible obstructive airway disease and for the treatment of exercise-induced bronchospasm (EIB).
A first-in-class, fixed-dose combination asthma rescue medication (delivered by a pressurised metered-dose inhaler) containing salbutamol/albuterol and budesonide (an anti-inflammatory inhaled corticosteroid), Airsupra®, was approved by the FDA in 2023.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Agonism of β2-adrenergic receptors in the lungs results in smooth muscle relaxation of bronchial smooth muscle. This is believed to be through the mechanism of increased cAMP production via adenylate cyclase activation. Increased levels of cAMP increase activity levels of protein kinase A which inhibits phosphorylation of myosin and lowers intracellular calcium concentrations leading to smooth muscle relaxation and bronchodilation. Salbutamol also inhibits the release of bronchoconstricting agents from mast cells, enhances mucociliary clearance and inhibits microvascular leakage.
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