Formoterol

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Formoterol
Formoterol.svg
Formoterol ball-and-stick model.png
Formoterol (top),
(R,R)-(−)-formoterol (center) and
(S,S)-(+)-formoterol (bottom)
Clinical data
Trade namesOxeze, Foradil, 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)
  • 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. 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.

It was patented in 1972 and came into medical use in 1998.[2] 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.[3]

At the current time,[when?] 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

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, Oxeze/Oxis, and Perforomist.

Uses and combinations[edit]

References[edit]

  1. ^ https://www.ema.europa.eu/documents/psusa/formoterol-list-nationally-authorised-medicinal-products-psusa/00001469/202005_en.pdf
  2. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 543. ISBN 9783527607495.
  3. ^ "Advair Diskus, Advair HFA, Brovana, Foradil, Perforomist, Serevent Diskus, and Symbicort Information (Long Acting Beta Agonists)". U.S. Food and Drug Administration (FDA).[dead link]

External links[edit]