Formoterol
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Formoterol (top),
(R,R)-(−)-formoterol (center) and
( S, S)-(+)-formoterol (bottom)
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Clinical data |
Trade names |
See below |
AHFS/Drugs.com |
Monograph |
License data |
- EU EMA: by formoterol fumarate dihydrate
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Pregnancy
category |
- AU: B3
- US: C (Risk not ruled out)
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Routes of
administration |
Inhalation (capsules for oral inhalation, DPI, MDI) |
ATC code |
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Legal status |
Legal status |
- UK: POM (Prescription only)
- US: ℞-only
- In general: ℞ (Prescription only)
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Pharmacokinetic data |
Protein binding |
61% to 64% |
Metabolism |
Hepatic demethylation and glucuronidation (CYP2D6, CYP2C19, CYP2C9 and CYP2A6 involved) |
Biological half-life |
10 h |
Excretion |
Renal and fecal |
Identifiers |
IUPAC name
- (RR,SS)-N-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl) propan-2-ylamino]ethyl] phenyl]formamide
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CAS Number |
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PubChem CID |
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IUPHAR/BPS |
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DrugBank |
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ChemSpider |
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UNII |
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KEGG |
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ChEBI |
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ChEMBL |
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ECHA InfoCard |
100.131.654 |
Chemical and physical data |
Formula |
C19H24N2O4 |
Molar mass |
344.405 g/mol |
3D model (JSmol) |
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Chirality |
Racemic mixture |
SMILES
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O=CNc1cc(ccc1O)[C@@H](O)CN[C@H](C)Cc2ccc(OC)cc2
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InChI
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InChI=1S/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1 Y
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Key:BPZSYCZIITTYBL-YJYMSZOUSA-N Y
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(verify) |
Not to be confused with Fenoterol.
Formoterol (INN) or eformoterol (former BAN) is a long-acting β2 agonist (LABA) used in the management of asthma and COPD. It is marketed in three forms: a dry-powder inhaler, a metered-dose inhaler and an inhalation solution, under various trade names including Atock, Atimos/Atimos Modulite, Foradil/Foradile, Oxeze/Oxis, and Perforomist. It is also marketed in the combination formulations budesonide/formoterol and mometasone/formoterol.
Formoterol has an extended duration of action (up to 12 h) compared to short-acting β2 agonists such as salbutamol (albuterol), which are effective for 4 h to 6 h. LABAs such as formoterol are used as "symptom controllers" to supplement prophylactic corticosteroid therapy. A "reliever" short-acting β2 agonist (e.g., salbutamol) is still required, since LABAs are not recommended for the treatment of acute asthma.
Contents
- 1 Mechanism of action
- 2 Safety
- 3 Additional potential uses
- 3.1 Stimulation of mitochondrial biogenesis
- 3.2 Treatment for Down syndrome
- 4 Trade names
- 5 See also
- 6 References
Mechanism of action
Inhaled formoterol works like other β2 agonists, causing bronchodilation by relaxing the smooth muscle in the airway so as to treat the exacerbation of asthma.
Safety
In November 2005, the US FDA released a health advisory alerting the public to findings that show the use of long-acting β2 agonists could lead to a worsening of wheezing symptoms in some patients.[1]
At the current time, available long-acting β2 agonists include salmeterol, formoterol, bambuterol, and sustained-release oral salbutamol.
Combinations of inhaled steroids and long-acting bronchodilators are becoming more widespread – combination preparations include fluticasone/salmeterol and budesonide/formoterol.
Additional potential uses
Stimulation of mitochondrial biogenesis
Formoterol may also help stimulate mitochondrial biogenesis. Mitochondrial dysfunction is related to many degenerative diseases — particularly neurodegenerative disorders.[2]
Treatment for Down syndrome
Preliminary research offers hope that formoterol may be a useful treatment in Down syndrome. In a mouse model of the disease, the drug strengthened nerve connections in the hippocampus, a brain center used for spatial navigation, paying attention and forming new memories.[3]
Trade names
Inhaler for a powder based in budesonide and formoterol
- Foradil/Foradile capsules for oral inhalation (Schering-Plough in the U.S., Novartis rest of world)
- Oxeze/Oxis Turbuhaler DPI (AstraZeneca)
- Atock (Astellas)
- Atimos/Atimos Modulite MDI (Chiesi)
- Perforomist inhalation solution (Mylan N.V.)
See also
- Arformoterol ((R,R)-(−)-formoterol) — an enantiopure compound used in the management of COPD
- Combination drugs:
- Aclidinium bromide/formoterol
- Budesonide/formoterol
- Mometasone furoate/formoterol
References
- ^ Center for Drug Evaluation and Research. "Advair Diskus, Advair HFA, Brovana, Foradil, Perforomist, Serevent Diskus, and Symbicort Information (Long Acting Beta Agonists)". Postmarket Drug Safety Information for Patients and Providers.
- ^ Wills, Lauren P; Trager, Richard E; Beeson, Gyda C; Lindsey, Christopher C; Peterson, Yuri K; Beeson, Craig C; Schnellmann, Rick G (April 6, 2012). "The β2-adrenoceptor agonist formoterol stimulates mitochondrial biogenesis". The Journal of Pharmacology and Experimental Therapeutics. 342 (1): 106–118. doi:10.1124/jpet.112.191528. ISSN 1521-0103. PMC 3383035 . PMID 22490378.
- ^ Dang, Van; Medina, Brian; Das, Devsmita; Moghadam, Sarah; Martin, Kara J.; Lin, Bill; Naik, Priyanka; Patel, Devan; Nosheny, Rachel; Wesson Ashford, John; Salehi, Ahmad (February 2014). "Formoterol, a Long-Acting β2 Adrenergic Agonist, Improves Cognitive Function and Promotes Dendritic Complexity in a Mouse Model of Down Syndrome". Biological Psychiatry. 75 (3): 179–188. doi:10.1016/j.biopsych.2013.05.024. ISSN 1873-2402. PMID 23827853.
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 |
- Beclometasone#
- Betamethasone
- Budesonide
- Ciclesonide
- Flunisolide
- Fluticasone
- Mometasone
- Triamcinolone
|
Anticholinergics/
muscarinic antagonist |
- Aclidinium bromide
- Glycopyrronium bromide
- Ipratropium bromide#
- Oxitropium bromide
- Tiotropium bromide
- Umeclidinium bromide
|
Mast cell stabilizers |
|
Xanthines |
- Acefylline
- Ambuphylline
- Bamifylline
- Doxofylline
- Enprofylline
- Etamiphylline
- Proxyphylline
- Theophylline/Aminophylline/Choline theophyllinate
|
Eicosanoid inhibition |
Leukotriene antagonists |
- Montelukast
- Pranlukast
- Zafirlukast
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Arachidonate 5-lipoxygenase inhibitors |
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Thromboxane receptor antagonists |
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Non-xanthine PDE4 inhibitors |
|
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Others/unknown |
- Amlexanox
- Eprozinol
- Fenspiride
- Omalizumab
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Combination products |
- Aclidinium/formoterol
- Beclometasone/formoterol
- Beclometasone/formoterol/glycopyrronium
- Budesonide/formoterol
- Fluticasone furoate/vilanterol
- Fluticasone propionate/salmeterol
- Indacaterol/glycopyrronium bromide
- Ipratropium bromide/salbutamol
- Mometasone/formoterol
- Umeclidinium bromide/vilanterol
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Adrenergic receptor modulators
|
α1 |
- Agonists: 6-FNE
- Amidephrine
- Anisodine
- Buspirone
- Cirazoline
- Corbadrine
- Desglymidodrine
- 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., brexpiprazole, 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
- Neldazosin
- Niaprazine
- Nicergoline
- Niguldipine
- Pardoprunox
- Pelanserin
- Perlapine
- Phendioxan
- Phenoxybenzamine
- Phentolamine
- Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione)
- Piperoxan
- Prazosin
- Quinazosin
- Quinidine
- Ritanserin
- Silodosin
- Spiperone
- Talipexole
- Tamsulosin
- Terazosin
- Tiodazosin
- Tolazoline
- 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
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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
- Rezatomidine
- Rilmenidine
- Romifidine
- Talipexole
- Tasipimidine
- Tetrahydrozoline
- Tiamenidine
- Tizanidine
- Tolonidine
- Urapidil
- Vatinoxan
- XP21279
- Xylazine
- Xylometazoline
- Antagonists: 1-PP
- Adimolol
- Amesergide
- Aptazapine
- Atipamezole
- Atypical antipsychotics (e.g., asenapine, brexpiprazole, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine)
- Azapirones (e.g., buspirone, gepirone, ipsapirone, 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
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β |
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