Formoterol

Not to be confused with Fenoterol.

Formoterol
Formoterol (top),
(R,R)-(−)-formoterol (center) and
(S,S)-(+)-formoterol (bottom)
Clinical data
Trade namesOxeze, Foradil, Symbicort, others
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: B3
Routes of
administration		Inhalation (capsules for oral inhalation, DPI, MDI)
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • NZ: Prescription only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only[1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding61% to 64%
MetabolismLiver demethylation and glucuronidation (CYP2D6, CYP2C19, CYP2C9 and CYP2A6 involved)
Elimination half-life10 h
ExcretionKidney and fecal
Identifiers
  • (RR,SS)-N-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl) propan-2-ylamino]ethyl] phenyl]formamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.131.654 Edit this at Wikidata
Chemical and physical data
FormulaC19H24N2O4
Molar mass344.411 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O=CNc1cc(ccc1O)[C@@H](O)CN[C@H](C)Cc2ccc(OC)cc2
  • 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 checkY
  • Key:BPZSYCZIITTYBL-YJYMSZOUSA-N checkY
  (verify)

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

Inhaler for a powder based in budesonide and formoterol

Formoterol 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.

In some countries, Perforomist is marketed by Viatris after Upjohn merged with Mylan to create Viatris.[7][8]

Uses and combinations

References

  1. ^ "List of nationally authorised medicinal products" (PDF). ema.europa.eu. Retrieved 17 June 2023.
  2. ^ 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.
  3. ^ Global Initiative for Asthma (2022). Global Strategy for Asthma Prevention and Management (Updated 2022) (PDF) (Report).
  4. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 543. ISBN 9783527607495.
  5. ^ "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.
  6. ^ "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.
  7. ^ "Pfizer Completes Transaction to Combine Its Upjohn Business with Mylan". Pfizer. 16 November 2020. Retrieved 17 June 2024 – via Business Wire.
  8. ^ "Brands". Viatris. 16 November 2020. Retrieved 17 June 2024.