Formoterol

Chemical compound

EU EMA: by formoterol fumarate dihydrate

Pregnancy
category

AU: B3

Routes of
administrationInhalation (capsules for oral inhalation, DPI, MDI)ATC code

R03AC13 (WHO) R03CC15 (WHO)

AU: S4 (Prescription only)
NZ: Prescription only
UK: POM (Prescription only)
US: ℞-only
EU: Rx-only^[1]
In general: ℞ (Prescription only)

Pharmacokinetic dataProtein binding61% to 64%MetabolismLiver demethylation and glucuronidation (CYP2D6, CYP2C19, CYP2C9 and CYP2A6 involved)Elimination half-life10 hExcretion Kidney and fecalIdentifiers

IUPAC name

(RR,SS)-N-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl) propan-2-ylamino]ethyl] phenyl]formamide

CAS Number

73573-87-2^Y

PubChem CID

3083544
3034756

IUPHAR/BPS

3465

DrugBank

DB00983^Y

ChemSpider

2340731^Y

UNII

5ZZ84GCW8B

KEGG

D07990^Y

ChEBI

CHEBI:408174^Y

ChEMBL

ChEMBL1363^Y

CompTox Dashboard (EPA)

DTXSID1023077

ECHA InfoCard100.131.654

Chemical and physical dataFormulaC₁₉H₂₄N₂O₄Molar mass344.411 g·mol⁻¹3D model (JSmol)

Interactive image

ChiralityRacemic mixture

SMILES

O=CNc1cc(ccc1O)[C@@H](O)CN[C@H](C)Cc2ccc(OC)cc2

InChI

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
Key:BPZSYCZIITTYBL-YJYMSZOUSA-N^Y

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Formoterol, also known as eformoterol, is a long-acting β₂ agonist (LABA) used as a bronchodilator in the management of asthma and chronic obstructive pulmonary disease (COPD). 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. Formoterol has a relatively rapid onset of action compared to other LABAs, and is effective within 2-3 minutes.^[2] The 2022 Global Initiative for Asthma report ^[3] recommends a combination formoterol/inhaled corticosteroid inhaler as both a preventer and reliever treatment for asthma in adults. In children, a short-acting β₂ adrenergic agonist (e.g., salbutamol) is still recommended.

It was patented in 1972 and came into medical use in 1998.^[4] It is available as a generic medication.^[5] It is also marketed in the combination formulations budesonide/formoterol and mometasone/formoterol.

Side effects

In November 2005, the US Food and Drug Administration (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.^[6]

Nowadays, 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.

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.

Society and culture

Brand names

It is marketed in three forms: a dry-powder inhaler (DPI), a metered-dose inhaler (MDI) and an inhalation solution, under various brand names including Atock, Atimos/Atimos Modulite, Foradil/Foradile, Fostair, Oxeze/Oxis, Perforomist and Symbicort.

Foradil/Foradile capsules for oral inhalation (Schering-Plough in the U.S., Novartis rest of world)
Oxeze/Oxis Turbuhaler Dry powder inhaler (DPI) (AstraZeneca)
Atock (Astellas)
Atimos/Atimos Modulite Metered-dose inhaler (MDI) (Chiesi)
Perforomist inhalation solution (Mylan N.V.)
Symbicort Turbohaler Dry powder inhaler (AstraZeneca)

Uses and combinations

Arformoterol ((R,R)-(−)-formoterol) — an enantiopure compound used in the management of COPD
Combination drugs:

References

^ "List of nationally authorised medicinal products" (PDF). ema.europa.eu. Retrieved 17 June 2023.
^ Anderson GP (1993). "Formoterol: pharmacology, molecular basis of agonism, and mechanism of long duration of a highly potent and selective beta 2-adrenoceptor agonist bronchodilator". Life Sci. 52 (26): 2145–60. doi:10.1016/0024-3205(93)90729-m. PMID 8099696.
^ Global Initiative for Asthma (2022). Global Strategy for Asthma Prevention and Management (Updated 2022) (PDF) (Report).
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 543. ISBN 9783527607495.
^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
^ "Advair Diskus, Advair HFA, Brovana, Foradil, Perforomist, Serevent Diskus, and Symbicort Information (Long Acting Beta Agonists)". U.S. Food and Drug Administration (FDA). Archived from the original on 1 November 2017. Retrieved 16 December 2019.

External links

"Formoterol". Drug Information Portal. U.S. National Library of Medicine.
"Formoterol fumarate". Drug Information Portal. U.S. National Library of Medicine.

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