4790
T3D4735
Salbutamol
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.
18559-94-9
2083
C13H21NO3
White powder.
147-149°C
1.41E+004 mg/L
Systemic absorption is rapid following aerosol administration.
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.
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
LD<sub>50</sub>=1100 mg/kg (orally in mice)
No indication of carcinogenicity to humans (not listed by IARC).
For symptomatic relief and prevention of bronchospasm due to bronchial asthma, chronic bronchitis, and other chronic bronchopulmonary disorders such as COPD.
2014-09-11T05:14:00Z
2014-12-24T20:26:56Z
Salbutamol
2549
DB01001
true
CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1
C13H21NO3
InChI=1/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-UHFFFAOYNA-N
239.3107
239.152143543
Exogenous
Solid
1.4
CHEMBL714
1999
<p>Toshikuni Kawazi, Masahiro Ono, Nobuko Inoue, “Salbutamol-containing plaster and method of producing same.” U.S. Patent US5068103, issued February, 1984.</p>