Fenoterol

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Fenoterol
Fenoterol.svg
Fenoterol ball-and-stick.png
Systematic (IUPAC) name
(RR,SS)-5-(1-hydroxy-2-{[2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)benzene-1,3-diol
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy cat. ? (AU) ? (US) ?
Legal status Pharmacist only (AU) Rx-Only (CA) POM (UK) -only (US)
Routes Inhalation
Identifiers
CAS number 13392-18-2 YesY
ATC code R03AC04 G02CA03
PubChem CID 3343
IUPHAR ligand 557
DrugBank DB01288
ChemSpider 3226 YesY
UNII 22M9P70OQ9 YesY
KEGG D04157 YesY
ChEBI CHEBI:149226 YesY
ChEMBL CHEMBL32800 YesY
Chemical data
Formula C17H21NO4 
Mol. mass 303.35 g/mol
 YesY (what is this?)  (verify)

Fenoterol is a Beta 2 adrenergic agonist designed to open up the airways to the lungs. It is classed as sympathomimetic beta2 agonist and asthma medication.

Fenoterol is produced and sold by Boehringer Ingelheim as Berotec N and in combination with ipratropium as Berodual N.

Side effects[edit]

Fenoterol 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 It was widely used in New Zealand in the early 1990s but withdrawn from that market[1] because of its association with an excess number of deaths.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[2] 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[edit]

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

References[edit]

  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. doi:10.1159/000237016. 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. doi:10.1056/NEJM199202203260801. PMID 1346340. 
  3. ^ Beale J. P., Stephenson N.C. (1972). "X-ray analysis of Th 1165 and salbutamol". , Journal of Pharmacy and Pharmacology 24: 277–280.