Editing Formoterol

{{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
| image_class = skin-invert-image
| 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}}
| pregnancy_AU = B3
| licence_EU = yes
| INN_EMA = formoterol fumarate dihydrate
| legal_AU = S4
| legal_CA =  
| legal_NZ = Prescription only
| legal_UK = POM
| legal_US = Rx-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 -->
| bioavailability =  
| 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|??}}
| CAS_number = 73573-87-2
| ATC_prefix = R03
| ATC_suffix = AC13
| ATC_supplemental = {{ATC|R03|CC15}}
| PubChem = 3083544
| PubChem2 = 3034756
| IUPHAR_ligand = 3465
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00983
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2340731
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5ZZ84GCW8B
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07990
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 408174
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1363

<!-- 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
| smiles = O=CNc1cc(ccc1O)[C@@H](O)CN[C@H](C)Cc2ccc(OC)cc2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BPZSYCZIITTYBL-YJYMSZOUSA-N
}}
<!-- Definition and medical uses -->
'''Formoterol''', also known as '''eformoterol''', is a [[Long-acting beta-adrenoceptor agonist|long-acting β<sub>2</sub> 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 β<sub>2</sub> 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 β<sub>2</sub> 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=dead }}</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 β<sub>2</sub> 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 β<sub>2</sub> 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|β<sub>2</sub> 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]]