Contemporany

science

(Salbutam

ol)

Joel Torres

Youssef Tahiri

Salbutamol Accession Number: DB01001 (APRD00553) Type: small molecule

Salbutamol (INN) or albuterol (USAN) is a short-acting β2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and chronic obstructive pulmonary disease. It is marketed as Ventolin among other brand names.

 

Systematic (IUPAC) name

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

Pharmacokinetic data

Metabolism: Hepatic

Half-life: 1.6 hours

Excretion: Renal

Identifiers

CAS number: 18559-94-9

ATC code: R03AC02 R03CC02

PubChem: CID 2083

IUPHAR ligand: 558

Drug Bank: DB01001

Chemical data

Formula: C13H21NO3

Mol. Mass: 239.311

Brand names

It is marketed by GlaxoSmithKline as Ventolin, Ventoline, Ventilan, Aerolin or Ventorlin, depending on the market; by Cipla as Asthalin and Asthavent; by Schering-Plough as Proventil, by Teva as ProAir, Salamol or Airomir, by Beximco (Bangladesh) as AZMASOL by Ad-din Pharma as Ventosol and by Alphapharm as Asmol.

Pharmacology

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.

Chemistry

Structure-activity relationshipsThe tertiary butyl group in salbutamol (or albuterol) makes it more selective for β₂-receptors. The drug is sold as a racemic mixture mainly because the (S)-enantiomer blocks metabolism pathways while the (R)-enantiomer shows activity.

SynthesisSalbutamol can be prepared from an acetophenone derivative which is itself derived from salicylic acid

Medical uses

Salbutamol is typically used to treat bronchospasm (due to any cause, allergen asthma or exercise-induced), as well as chronic obstructive pulmonary disease. The dose of Salbutamol remains controversial. It is marketed as a metered dose inhaler which produces an average of 90 micrograms per puff.

Adverse effects

The most common side effects are fine tremor, anxiety, headache, muscle cramps, dry mouth, and palpitation. Other symptoms may include tachycardia, arrhythmia, flushing, myocardial ischemia (rare), and disturbances of sleep and behaviour.

Society and culture

Doping

Clinical studies show no compelling evidence that salbutamol and other β2-agonists can increase performance in healthy athletes. In spite of this, salbutamol required "a declaration of Use in accordance with the International Standard for Therapeutic Use Exemptions" under the 2010 WADA prohibited list.

Detection of useSalbutamol may be quantified in blood or plasma to confirm a diagnosis of poisoning in hospitalized patients or to aid in a forensic investigation. Urinary salbutamol concentrations are frequently measured in competitive sports programs, for which a level in excess of 1000 μg/L is considered to represent abuse.