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Formoterol

From Wikipedia, the free encyclopedia

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

[edit]

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

[edit]

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

[edit]

Brand names

[edit]
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

[edit]

References

[edit]
  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.