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Formoterol

From Wikipedia, the free encyclopedia
Long-acting bronchiodilator
Not to be confused withFenoterol.

Pharmaceutical compound
Formoterol
Formoterol molecular structure
Above (R,R)-(−)-formoterol
Below (S,S)-(+)-formoterol
Clinical data
Trade namesOxeze, Foradil, Symbicort, others
AHFS/Drugs.comMonograph
License data
Pregnancy
category
Routes of
administration
Inhalation (capsules for oral inhalation,DPI,MDI)
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding61% to 64%
MetabolismLiverdemethylation andglucuronidation (CYP2D6,CYP2C19,CYP2C9 andCYP2A6 involved)
Eliminationhalf-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
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.131.654Edit 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 aseformoterol, is along-acting β2 agonist (LABA) used as abronchodilator in the management ofasthma andchronic obstructive pulmonary disease (COPD). Formoterol has an extended duration of action (up to 12 h) compared to short-acting β2 agonists such assalbutamol (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 2022Global 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 ageneric medication.[5] It is also marketed in the combination formulationsbudesonide/formoterol andmometasone/formoterol.

Side effects

[edit]

In November 2005, the USFood 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 includesalmeterol, formoterol,bambuterol, and sustained-release oralsalbutamol.

Combinations of inhaled steroids and long-acting bronchodilators are becoming more widespread – combination preparations includefluticasone/salmeterol andbudesonide/formoterol.

Mechanism of action

[edit]

Inhaled formoterol works like otherβ2 agonists, causing bronchodilation by relaxing the smooth muscle in the airway so as to treat the exacerbation of asthma.It has also been reported to targettubulin, favorizing its polymerization.[7]

Society and culture

[edit]

Brand names

[edit]
Inhaler for a powder based inbudesonide and formoterol

Formoterol is marketed in three forms: adry-powder inhaler (DPI), ametered-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 byViatris after Upjohn merged with Mylan to create Viatris.[8][9]

Uses and combinations

[edit]

References

[edit]
  1. ^"List of nationally authorised medicinal products"(PDF).ema.europa.eu. Retrieved17 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 fromthe original on 29 June 2023. Retrieved29 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 fromthe original on 1 November 2017. Retrieved16 December 2019.
  7. ^Baksheeva VE, La Rocca R, Allegro D, Derviaux C, Pasquier E, Roche P, et al. (2025). "NanoDSF Screening for Anti-tubulin Agents Uncovers New Structure–Activity Insights".Journal of Medicinal Chemistry.doi:10.1021/acs.jmedchem.5c01008.
  8. ^"Pfizer Completes Transaction to Combine Its Upjohn Business with Mylan". Pfizer. 16 November 2020. Retrieved17 June 2024 – via Business Wire.
  9. ^"Brands".Viatris. 16 November 2020. Retrieved17 June 2024.
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