Formoterol

Not to be confused with Fenoterol.
Formoterol
Formoterol (top),
(R,R)-(−)-formoterol (center) and
(S,S)-(+)-formoterol (bottom)
Names
Trade namesOxeze, Perforomist, others
IUPAC name
  • (RR,SS)-N-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl) propan-2-ylamino]ethyl] phenyl]formamide
Clinical data
Drug classLABA[1]
Main usesAsthma, COPD[2]
Side effectsDry mouth, trouble sleeping, nausea, throat inflammation[1]
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Pregnancy
category
  • AU: B3
    Routes of
    use    		Inhalation (capsules for oral inhalation, DPI, MDI)
    Onset of actionUp to 3 hr for max. effect[1]
    Duration of action12 h[1]
    External links
    AHFS/Drugs.comMonograph
    Legal
    License data
    Legal status
    • AU: S4 (Prescription only)
    • UK: POM (Prescription only)
    • US: ℞-only
    • EU: Rx-only [3]
    • In general: ℞ (Prescription only)
    Pharmacokinetics
    Protein binding61% to 64%
    MetabolismLiver demethylation and glucuronidation (CYP2D6, CYP2C19, CYP2C9 and CYP2A6 involved)
    Elimination half-life10 h
    ExcretionKidney and fecal
    Chemical and physical data
    FormulaC19H24N2O4
    Molar mass344.411 g·mol−1
    3D model (JSmol)
    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 checkY
    • Key:BPZSYCZIITTYBL-YJYMSZOUSA-N checkY

    Formoterol, also known as eformoterol, is a used in the long term management of asthma and chronic obstructive pulmonary disease (COPD).[2] It is used by breathing it into the lungs.[2] Full effects take about 2 hours and last about 12 h.[1]

    Common side effects include dry mouth, trouble sleeping, nausea, and throat inflammation.[1] Other side effects may include bronchospasm, anaphylaxis, and QT prolongation.[1] In asthma, it may increase the risk of death if used without an inhaled steroid.[1] Use in pregnancy is of unclear safety.[1] It is a long-acting β2 agonist (LABA).[1]

    Formoterol was patented in 1972 and came into medical use in 1998.[4] It is available as a generic medication.[5] In the United Kingdom it costs the NHS about £12 per month as of 2021.[2] In the United States this amount costs about 285 USD.[5] It is also available in combination as budesonide/formoterol and mometasone/formoterol.[2][1]

    Medical uses

    Dosage

    It is often used at a dose of 12 micrograms twice per day.[2]

    Combinations

    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.[6]

    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

    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.

    References

    1. 1 2 3 4 5 6 7 8 9 10 11 "Formoterol Monograph for Professionals". Drugs.com. Archived from the original on 28 November 2021. Retrieved 13 December 2021.
    2. 1 2 3 4 5 6 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 267. ISBN 978-0857114105.
    3. ↑ "Archive copy" (PDF). Archived (PDF) from the original on 2021-10-31. Retrieved 2021-07-12.{{cite web}}: CS1 maint: archived copy as title (link)
    4. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 543. ISBN 9783527607495. Archived from the original on 2021-07-24. Retrieved 2021-07-12.
    5. 1 2 "Formoterol Prices, Coupons & Savings Tips - GoodRx". GoodRx. Retrieved 13 December 2021.
    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 2017-11-01. Retrieved 2021-07-12.
    External sites:
    Identifiers:
    • "Formoterol fumarate". Drug Information Portal. U.S. National Library of Medicine. Archived from the original on 2021-04-15. Retrieved 2021-07-12.
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