The Full Wiki

More info on Fenoterol

Fenoterol: Wikis

  
  

Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.

Encyclopedia

From Wikipedia, the free encyclopedia

Fenoterol
Systematic (IUPAC) name
(RR,SS)-5-(1-hydroxy-2-{[2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)benzene-1,3-diol
Identifiers
CAS number 13392-18-2
ATC code R03AC04 G02CA03
PubChem 3343
Chemical data
Formula C17H21NO4 
Mol. mass 303.35 g/mol
SMILES eMolecules & PubChem
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes Inhaled
 Yes check.svgY(what is this?)  (verify)

Fenoterol is an asthma medication designed to open up the airways to the lungs. It is classed as a beta agonist.

Fenoterol was marketed as "Berotec" by Boehringer-Ingelheim.

It is still marketed in at least Lithuania (over the counter) as fenoteroli in combination with iprotropii as the medication Berodual N, which appears to be made in Germany by Boehringer Ingelheim. http://www.pharmacy1010.com/product_page.asp?id=1474

Side effects

It was a short-acting beta-agonist widely used in New Zealand in the early 1990s but withdrawn[1] because of its association with an excess number of deaths.

This was due to its additional effects on the β2 receptors that lead to cardiovascular adverse effects, notably dysrhythmia and cardiac hypoxia. Fenoterol increased the risk of death because it was typically used in excessively large doses for severe asthma attacks[2] in the absence of medical assistance. Instances were known of patients who had used up to 80 puffs before seeking medical attention.

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)-enantiomers. This racemate is 9- to 20-times more effective, as compared to the racemate of the (R,S)- and (S,R)-enantiomers.[3]

Four stereoisomeres of 5-(1-hydroxy-2-{[2-(4-hydroxyphenyl)-1-
methylethyl]amino}ethyl)benzene-1,3-diol

References

  1. ^ Beasley R, Pearce N, Crane J, Burgess C (1995). "Withdrawal of fenoterol and the end of the New Zealand asthma mortality epidemic". International archives of allergy and immunology 107 (1-3): 325–7. PMID 7613161. 
  2. ^ Spitzer WO, Suissa S, Ernst P, et al. (February 1992). "The use of beta-agonists and the risk of death and near death from asthma". The New England journal of medicine 326 (8): 501–6. PMID 1346340. 
  3. ^ J. P. Beale und N.C. Stephenson: X-ray analysis of Th 1165 and salbutamol, Journal of Pharmacy and Pharmacology 24 (1972) 277-280.







Got something to say? Make a comment.
Your name
Your email address
Message