Fenoterol

Not to be confused with Formoterol.

Fenoterol is a β₂-adrenergic receptor agonist and bronchodilator medication used in the treatment of asthma.

Fenoterol

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	AU: A
Routes of administration	Inhalation
ATC code	R03AC04 (WHO) G02CA03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)
Pharmacokinetic data
Elimination half-life	~6.5 hours[1][2][3][4]
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
PubChem CID	3343
IUPHAR/BPS	557
DrugBank	DB01288 Y
ChemSpider	3226 Y
UNII	22M9P70OQ9
KEGG	D04157 Y
ChEBI	CHEBI:149226 Y
ChEMBL	ChEMBL32800 Y
CompTox Dashboard (EPA)	DTXSID4023046
ECHA InfoCard	100.205.960
Chemical and physical data
Formula	C17H21NO4
Molar mass	303.358 g·mol−1
3D model (JSmol)	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
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Fenoterol is produced and sold by Boehringer Ingelheim as Berotec N and in combination with ipratropium as Berodual N.

It was patented in 1962 and came into medical use in 1971,^[5] but in the 1980s concerns emerged about its safety and its use being associated with an increased risk of death.

Adverse effects

Fenoterol branded as Berotec

Fenoterol is a short-acting β₂ agonist that also stimulates β₁ receptors. Fenoterol has more cardiovascular toxicity than isoprenaline or salbutamol.^[6][7] Fenoterol was widely used in New Zealand in the late 1970s and the 1980s until it was removed from the New Zealand drug tariff in 1989 because its introduction and widespread use was associated with an epidemic of asthma deaths.^[8] A series of case-control studies demonstrated that asthmatics using fenoterol were more likely to die of asthma compared with controls treated with alternative beta agonists; this risk of asthma deaths was particularly high in severe asthmatics.^[9][10] The mortality rate declined following withdrawal of fenoterol^[11] without evidence supporting an alternative explanation for the abrupt rise and fall in asthma deaths.^[12] Data did not support confounding by severity as the explanation for the excess mortality.^[13] There are alternative short-acting beta agonists that have not been associated with increased mortality (e.g. salbutamol [albuterol]).^{[citation needed]}

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)-, (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.^[14]

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