Fenoterol

Fenoterol

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	US: B (No risk in non-human studies)
Routes of administration	Inhalation (MDI)
ATC code	R03AC04 (WHO) G02CA03 (WHO)
Legal status
Legal status	AU: S3 (Pharmacist only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Identifiers
IUPAC name (RR,SS)-5-(1-hydroxy-2-{[2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)benzene-1,3-diol
CAS Number	13392-18-2 Y
PubChem CID	3343
IUPHAR/BPS	557
DrugBank	DB01288 Y
ChemSpider	3226 Y
UNII	22M9P70OQ9
KEGG	D04157 Y
ChEBI	CHEBI:149226 Y
ChEMBL	CHEMBL32800 Y
ECHA InfoCard	100.205.960
Chemical and physical data
Formula	C17H21NO4
Molar mass	303.35 g/mol
3D model (Jmol)	Interactive image
SMILES Oc1cc(cc(O)c1)C(O)CNC(C)Cc2ccc(O)cc2
InChI InChI=1S/C17H21NO4/c1-11(6-12-2-4-14(19)5-3-12)18-10-17(22)13-7-15(20)9-16(21)8-13/h2-5,7-9,11,17-22H,6,10H2,1H3 Y Key:LSLYOANBFKQKPT-UHFFFAOYSA-N Y

Fenoterol is a β₂ adrenoreceptor agonist designed to open up the airways to the lungs. It is classed as sympathomimetic β₂ agonist and asthma medication.

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

Fenoterol is a short-acting β₂ agonist, which also stimulates β₁ receptors at doses above the recommended therapeutic doses. It was widely used in New Zealand in the early 1990s but withdrawn from that market because of its association with an excess number of deaths.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 β agonists in acute asthma not responding to usual doses, are now generally recognized as undesirable with all β agonist asthma inhalers.

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)-, (R,S)-, (S,R)- and (S,S)-stereoisomers (see the figure below). 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.