Fenoterol
Encyclopedia
Fenoterol is an asthma medication designed to open up the airways to the lungs. It is classed as sympathomimetic beta2 agonist.

Fenoterol is produced and sold by Boehringer Ingelheim as Berotec N and in combination with ipratropium
Ipratropium
Ipratropium bromide is an anticholinergic drug used for the treatment of chronic obstructive pulmonary disease and acute asthma. It blocks the muscarinic acetylcholine receptors in the smooth muscles of the bronchi in the lungs, opening the bronchi...

 as Berodual N.

Side effects

Fenterol is a short-acting beta2-agonist, which also stimulates beta1 receptors at doses above the recommended therapeutic doses. It was widely used in New Zealand
New Zealand
New Zealand is an island country in the south-western Pacific Ocean comprising two main landmasses and numerous smaller islands. The country is situated some east of Australia across the Tasman Sea, and roughly south of the Pacific island nations of New Caledonia, Fiji, and Tonga...

 in the early 1990s but withdrawn from that market because of its association with an excess number of deaths.

It is thought that the association of increased risk of death was because it was typically used in excessively large doses for severe acute asthma attacks in the absence of medical assistance. Instances were known of patients who had used up to 80 puffs before seeking medical attention. Both excessive prescribed doses and patient's excessive self-medication with beta-agonists in acute asthma not responding to usual doses, are now generally recognised as undesirable with all beta-agonist asthma inhalers.

Stereoisomers

5-(1-Hydroxy-2-{[2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)benzene-1,3-diol is a molecule with two different stereogenic centers. Thus, four stereoisomers may exist, the (R,R)-, (S,S)-, (R,S)-, and (S,R)-stereoisomers (Scheme). Fenoterol is a racemate of the (R,R)- and the (S,S)-enantiomer
Enantiomer
In chemistry, an enantiomer is one of two stereoisomers that are mirror images of each other that are non-superposable , much as one's left and right hands are the same except for opposite orientation. It can be clearly understood if you try to place your hands one over the other without...

s. This racemate is 9 to 20 times more effective, as compared to the racemate of the (R,S)- and (S,R)-enantiomers.
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