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^Y
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
(verify)

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.

Side effects

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 It was widely used in New Zealand in the early 1990s but withdrawn from that market^[1] because of its association with an excess number of deaths.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 β agonists in acute asthma not responding to usual doses, are now generally recognized as undesirable with all β 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)-, (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.^[3]

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

References

↑ 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.
↑ 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.
↑ Beale J. P.; Stephenson N.C. (1972). "X-ray analysis of Th 1165 and salbutamol". Journal of Pharmacy and Pharmacology. 24: 277–280.

Drugs for obstructive airway diseases: asthma/COPD (R03)

Adrenergics, inhalants

Short-acting β₂ agonists	Bitolterol Carbuterol Fenoterol Isoetarine Pirbuterol Procaterol Reproterol Rimiterol Salbutamol (albuterol)^#/Levosalbutamol (levalbuterol) Terbutaline Tulobuterol

Long-acting β₂ agonists	Bambuterol Clenbuterol Formoterol/Arformoterol Salmeterol Salmefamol

Ultra-long-acting β₂ agonists	Abediterol Carmoterol Indacaterol Olodaterol Vilanterol

Other	Epinephrine^# Hexoprenaline Isoprenaline (isoproterenol) Orciprenaline (metaproterenol)

Glucocorticoids

Anticholinergics/
muscarinic antagonist

Mast cell stabilizers

Xanthines

Eicosanoid inhibition

Leukotriene antagonists	Montelukast Pranlukast Zafirlukast

Arachidonate 5-lipoxygenase inhibitors	Zileuton

Thromboxane receptor antagonists	Ramatroban Seratrodast

Non-xanthine PDE4 inhibitors	Ibudilast Roflumilast

Others/unknown

Combination products

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Tocolytics/labor repressants (G02CA)

β₂ adrenoreceptor agonists	Buphenine Fenoterol Hexoprenaline Ritodrine Terbutaline

Oxytocin antagonists	Atosiban

NSAIDs	Indometacin

Calcium channel blockers	Nifedipine

Myosin inhibitors	Magnesium sulfate

Adrenergic receptor modulators

α₁

Agonists 6-FNE Amidephrine Anisodine Buspirone Cirazoline Corbadrine Dexisometheptene Dipivefrine Dopamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etilefrine Etilevodopa Ethylnorepinephrine Indanidine Isometheptene L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Melevodopa Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetryzoline Tiamenidine XP21279 Xylometazoline

Antagonists Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, risperidone) Benoxathian Buflomedil Bunazosin Carvedilol Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride) Etoperidone Eugenodilol Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 Labetalol mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Nefazodone Neldazosin Niaprazine Nicergoline Niguldipine Pardoprunox Pelanserin Phendioxan Phenoxybenzamine Phentolamine Piperoxan Prazosin Quinazosin Ritanserin Silodosin Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Trazodone Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine) Trimazosin Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Urapidil WB-4101 Zolertine

α₂

Agonists (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Droxidopa (L-DOPS) Etilevodopa Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Lofexidine Medetomidine Melevodopa Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rilmenidine Romifidine Talipexole Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil XP21279 Xylazine Xylometazoline

Antagonists 1-PP Adimolol Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine) Azapirones (e.g., buspirone, tandospirone) BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan mCPP Mianserin Mirtazapine NAN-190 Olanzapine Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine SB-269970 Setiptiline Spiroxatrine Sunepitron Tolazoline Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Yohimbine

Agonists Abediterol Alifedrine Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Carmoterol Cimaterol Clenbuterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etafedrine Etilefrine Etilevodopa Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Levosalbutamol Mabuterol Melevodopa Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine PF-610355 Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol XP21279 Zilpaterol Zinterol

Antagonists Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

See also: Dopaminergics

Melatonergics

Serotonergics

Monoamine reuptake and release modulators

Monoamine metabolism modulators

Monoamine neurotoxins

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