Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Formoterol: Difference between pages

{{Short description|Long-acting bronchiodilator}}

{{distinguish|Fenoterol}}

{{Use dmy dates|date=June 2024}}

{{cs1 config |name-list-style=vanc |display-authors=6}}

{{Infobox drug

| verifiedrevid = 461113044

| image = Formoterol.svg

| width = 230

| alt =

| image2 = Formoterol ball-and-stick model.png

| alt2 =

| caption = Formoterol (top),<br />(''R'',''R'')-(−)-formoterol (center) and<br />(''S'',''S'')-(+)-formoterol (bottom)

| chirality = [[Racemic mixture]]

<!-- Clinical data -->

| tradename = Oxeze, Foradil, Symbicort, others

| Drugs.com = {{drugs.com|monograph|formoterol-fumarate}}

| licence_EU = yes

| INN_EMA = formoterol fumarate dihydrate

| legal_AU = S4

| legal_NZ = Prescription only

| legal_EU = Rx-only

| legal_EU_comment = <ref>{{cite web|url=https://www.ema.europa.eu/documents/psusa/formoterol-list-nationally-authorised-medicinal-products-psusa/00001469/202005_en.pdf |title=List of nationally authorised medicinal products|website=ema.europa.eu|access-date=17 June 2023}}</ref>

| legal_status = Rx-only

| routes_of_administration = Inhalation ([[Capsule (pharmacy)|capsules]] for oral inhalation, [[Dry powder inhaler|DPI]], [[Metered-dose inhaler|MDI]])

<!-- Pharmacokinetic data -->

| protein_bound = 61% to 64%

| metabolism = [[Liver]] [[demethylation]] and [[glucuronidation]] ([[CYP2D6]], [[CYP2C19]], [[CYP2C9]] and [[CYP2A6]] involved)

| elimination_half-life = 10 h

| excretion = [[Kidney]] and fecal

<!-- Identifiers -->

| index_label =

| index2_label =

| CAS_number_Ref = {{cascite|correct|??}}

| ATC_supplemental = {{ATC|R03|CC15}}

| PubChem2 = 3034756

| IUPHAR_ligand = 3465

<!-- Chemical data -->

| IUPAC_name = (''RR'',''SS'')-''N''-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl) propan-2-ylamino]ethyl] phenyl]formamide

| C=19 | H=24 | N=2 | O=4

<!-- Definition and medical uses -->

'''Formoterol''', also known as '''eformoterol''', is a [[Long-acting beta-adrenoceptor agonist|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&nbsp;h) compared to short-acting β₂ agonists such as [[salbutamol]] (albuterol), which are effective for 4&nbsp;h to 6&nbsp;h. Formoterol has a relatively rapid onset of action compared to other LABAs, and is effective within 2-3&nbsp;minutes.<ref name="pmid8099696">{{cite journal| author=Anderson GP| title=Formoterol: pharmacology, molecular basis of agonism, and mechanism of long duration of a highly potent and selective beta 2-adrenoceptor agonist bronchodilator. | journal=Life Sci | year= 1993 | volume= 52 | issue= 26 | pages= 2145–60 | pmid=8099696 | doi=10.1016/0024-3205(93)90729-m | pmc= | url=https://pubmed.ncbi.nlm.nih.gov/8099696 }}</ref> The 2022 [[Global Initiative for Asthma]] report <ref>{{cite report |author=Global Initiative for Asthma|date=2022 |title=Global Strategy for Asthma Prevention and Management (Updated 2022) |url=https://ginasthma.org/wp-content/uploads/2022/07/GINA-Main-Report-2022-FINAL-22-07-01-WMS.pdf}}</ref> 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.

<!-- Society and culture -->

It was patented in 1972 and came into medical use in 1998.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=543 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA543 |language=en}}</ref> It is available as a [[generic medication]].<ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. [[Food and Drug Administration]] (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=live }}</ref> 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.<ref>{{cite web | work=U.S. [[Food and Drug Administration]] (FDA) | title=Advair Diskus, Advair HFA, Brovana, Foradil, Perforomist, Serevent Diskus, and Symbicort Information (Long Acting Beta Agonists) | url=https://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm108111.htm | access-date=16 December 2019 | archive-date=1 November 2017 | archive-url=https://web.archive.org/web/20171101115959/https://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm108111.htm | url-status=dead }}</ref>

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 [[beta2-adrenergic receptor agonist|β₂ agonist]]s, causing bronchodilation by relaxing the smooth muscle in the airway so as to treat the exacerbation of asthma.

== Society and culture ==

=== Brand names ===

[[File:Budesonide and formoterol inhaler.jpg|thumb|200px|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.

* Foradil/Foradile [[Capsule (pharmacy)|capsules]] for oral inhalation ([[Schering-Plough]] in the U.S., [[Novartis]] rest of world)

* Oxeze/Oxis Turbuhaler dry-powder inhaler (DPI) ([[AstraZeneca]])

* Atock ([[Astellas Pharma|Astellas]])

* Atimos/Atimos Modulite metered-dose inhaler (MDI) ([[Chiesi Farmaceutici S.p.A.|Chiesi]])

* Perforomist inhalation [[Solution (chemistry)|solution]] ([[Mylan|Mylan N.V.]])

* Symbicort Turbuhaler dry-powder inhaler (DPI) (AstraZeneca)

In some countries, Perforomist is marketed by [[Viatris]] after Upjohn merged with Mylan to create Viatris.<ref>{{cite web | title=Pfizer Completes Transaction to Combine Its Upjohn Business with Mylan | publisher=Pfizer | via=Business Wire | date=16 November 2020 | url=https://www.businesswire.com/news/home/20201116005378/en/ | access-date=17 June 2024}}</ref><ref>{{cite web | title=Brands | website=Viatris | date=16 November 2020 | url=https://www.viatris.com/en/products/brands | access-date=17 June 2024}}</ref>

==Uses and combinations==

* [[Arformoterol]] ((''R'',''R'')-(−)-formoterol) — an [[Enantiopure drug|enantiopure]] compound used in the management of [[Chronic obstructive pulmonary disease|COPD]]

* Combination drugs:

** [[Aclidinium bromide/formoterol]]

** [[Budesonide/formoterol]]

** [[Mometasone/formoterol|Mometasone furoate/formoterol]]

==References==

{{reflist}}

{{Asthma and copd rx}}

{{Adrenergic agonists}}

{{Portal bar | Medicine}}

[[Category:Beta2-adrenergic agonists]]

[[Category:4-Methoxyphenyl compounds]]

[[Category:Phenols]]

[[Category:Drugs developed by Schering-Plough]]

[[Category:Drugs developed by Merck & Co.]]

[[Category:Drugs developed by AstraZeneca]]

[[Category:Drugs developed by Novartis]]

[[Category:Formamides]]

[[Category:Substituted amphetamines]]

[[Category:Phenylethanolamines]]

[[pnb:آمو دریا]]