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

{{Short description|Medication}}

{{Other uses|Fluticasone}}

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

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

{{Infobox drug

| verifiedrevid = 461102778

| image = Fluticasone_propionate.svg

| width =

| alt =

| caption =

| image2 = Fluticasone-propionate-3D-bs-17.png

<!-- Clinical data -->

| pronounce =

| tradename = Flovent, Flixotide, Flonase, others

| MedlinePlus = a695002

| DailyMedID = Fluticasone propionate

| pregnancy_AU = B3

| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Fluticasone Use During Pregnancy | website=Drugs.com | date=9 January 2019 | url=https://www.drugs.com/pregnancy/fluticasone.html | access-date=31 January 2020 | archive-date=26 March 2019 | archive-url=https://web.archive.org/web/20190326052503/https://www.drugs.com/pregnancy/fluticasone.html | url-status=live }}</ref>

| pregnancy_category=

| routes_of_administration = [[Intranasal]],<ref name="Flonase Allergy Relief FDA label"/> [[Inhalation administration|inhalation]],<ref name="Flovent Diskus FDA label"/> [[Topical administration|topical]]<ref name="Cutivate FDA label">{{cite web | title=Cutivate- fluticasone propionate lotion | website=DailyMed | date=8 August 2018 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cc79e200-ce69-4ffd-be5b-8c1a6bb88c5c | access-date=19 February 2022 | archive-date=20 February 2022 | archive-url=https://web.archive.org/web/20220220073758/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cc79e200-ce69-4ffd-be5b-8c1a6bb88c5c | url-status=live }}</ref>

| class = Steroids and steroid derivatives

| ATC_prefix = D07

| ATC_suffix = AC17

| ATC_supplemental = {{ATC|R01|AD08}} {{ATC|R03|BA05}} {{ATC|R01|AD58}}

<!-- Legal status -->

| legal_AU = S4

| legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | access-date=30 March 2024}}</ref>

| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->

| legal_BR_comment =

| legal_CA = Rx-only

| legal_CA_comment = <ref>{{cite web | title=Respiratory health | website=[[Health Canada]] | date=9 May 2018 | url=https://www.canada.ca/en/services/health/drug-health-products/drug-medical-device-highlights-2017/approved-drugs/respiratory-health.html | access-date=13 April 2024}}</ref>

| legal_DE = <!-- Anlage I, II, III or Unscheduled-->

| legal_DE_comment =

| legal_NZ = <!-- Class A, B, C -->

| legal_NZ_comment =

| legal_UK_comment = /&nbsp;[[Prescription drug|POM]]&nbsp;(Prescription)<ref>{{cite web | title=Flixonase Aqueous Nasal Spray - Summary of Product Characteristics (SmPC) | website=(emc) | date=25 October 2019 | url=https://www.medicines.org.uk/emc/product/845/smpc | access-date=31 January 2020 | archive-date=31 January 2020 | archive-url=https://web.archive.org/web/20200131185252/https://www.medicines.org.uk/emc/product/845/smpc | url-status=live }}</ref>

| legal_US = OTC

| legal_US_comment = /&nbsp;[[Rx-only]]<ref name="Cutivate FDA label" />

| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->

| legal_UN_comment =

| legal_status = <!--For countries not listed above-->

<!-- Pharmacokinetic data -->

| metabolism = Intranasal<br />[[Liver]] ([[CYP3A4]]-mediated)

| metabolites =

| >

| duration_of_action =

| excretion = [[Kidney]]

<!-- Identifiers -->

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

| CAS_supplemental =

| IUPHAR_ligand = 7080

| KEGG_Ref =

| KEGG = D01708

| NIAID_ChemDB =

| PDB_ligand =

| synonyms =

<!-- Chemical and physical data -->

| IUPAC_name = S-(fluoromethyl)-6α,9-difluoro-11β, 17-dihydroxy-16α-methyl-3-oxoandrosta-1, 4-diene-17β-carbothioate, 17-propanoate

| C=25 | H=31 | F=3 | O=5 | S=1

| SMILES = CCC(=O)OC1(C(CC2C1(CC(C3(C2CC(C4=CC(=O)C=CC43C)F)F)O)C)C)C(=O)SCF

| StdInChI_comment =

| density =

| density_notes =

| melting_point =

| melting_high =

| melting_notes =

| boiling_point =

| boiling_notes =

| solubility =

| sol_units =

| specific_rotation =

<!-- Definition and medical uses -->

'''Fluticasone propionate''', sold under the brand names '''Flovent''' and '''Flonase''' among others, is a [[glucocorticoid|steroid]] medication.<ref name=AHFS2019Inhaled>{{cite web |title=Fluticasone Propionate Monograph for Professionals |url=https://www.drugs.com/monograph/fluticasone-propionate.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=27 February 2019 |archive-date=28 February 2019 |archive-url=https://web.archive.org/web/20190228004035/https://www.drugs.com/monograph/fluticasone-propionate.html |url-status=live }}</ref> When inhaled it is used for the long term management of [[asthma]] and [[COPD]].<ref name=AHFS2019Inhaled/> In the nose it is used for [[hay fever]] and [[nasal polyps]].<ref name=AHFS2019ENT>{{cite web |title=Fluticasone Propionate eent Monograph for Professionals |url=https://www.drugs.com/monograph/fluticasone-propionate-eent.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=27 February 2019 |archive-date=28 February 2019 |archive-url=https://web.archive.org/web/20190228003943/https://www.drugs.com/monograph/fluticasone-propionate-eent.html |url-status=live }}</ref><ref name=BNF76/> It can also be used for [[mouth ulcer]]s.<ref name=She2019>{{cite web|url=https://publicdocuments.sth.nhs.uk/pil2057.pdf|title=Flixonase aqueous spray|date=June 2018|website=Sheffield Teaching Hospitals|access-date=31 January 2020|archive-date=25 September 2019|archive-url=https://web.archive.org/web/20190925231108/https://publicdocuments.sth.nhs.uk/pil2057.pdf|url-status=dead}}</ref> It works by decreasing [[inflammation]].

<!-- Side effects and mechanisms -->

Common side effects when inhaled include [[upper respiratory tract infection]]s, [[sinusitis]], [[Candidiasis|thrush]], and [[cough]].<ref name=AHFS2019Inhaled/> Common side effects when used in the nose include [[nosebleeding]] and sore throat.<ref name=AHFS2019ENT/>

<!-- Society and culture -->

Fluticasone propionate was patented in 1980, and approved for medical use in 1990.<ref>{{cite book |vauthors=Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=487 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA487 |access-date=19 September 2020 |archive-date=28 November 2023 |archive-url=https://web.archive.org/web/20231128055118/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA487#v=onepage&q&f=false |url-status=live }}</ref> It is available as a [[generic medication]].<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=262, 1172|edition=76}}</ref> In 2021, fluticasone was the 23rd most commonly prescribed medication in the United States, with more than 25{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title=Fluticasone - Drug Usage Statistics | website=ClinCalc | url=https://clincalc.com/DrugStats/Drugs/Fluticasone | access-date=14 January 2024 }}</ref>

==Medical uses==

Fluticasone propionate is used by powder or aerosol [[inhalation]] for the prophylaxis of asthma.<ref name="Flovent Diskus FDA label"/><ref name=AHFS2019Inhaled/> The [[nasal spray]] is used for prevention and treatment of [[allergic rhinitis]].<ref name="Flonase Allergy Relief FDA label"/> Nasal drops are used in the treatment of [[nasal polyp]]s. The nasal spray can also be used in the mouth for [[mouth ulcer]]s.<ref name=She2019 />

Fluticasone propionate in a topical form can be used to treat skin conditions such as [[eczema]], [[psoriasis]], and [[rashes]].<ref>{{cite web |title=Drugs & Medications |url=https://www.webmd.com/drugs/2/drug-8786/fluticasone-propionate-topical/details |website=www.webmd.com |access-date=13 April 2020 |language=en |archive-date=22 October 2020 |archive-url=https://web.archive.org/web/20201022160624/https://www.webmd.com/drugs/2/drug-8786/fluticasone-propionate-topical/details |url-status=live }}</ref><ref name=":3">{{cite journal |vauthors=Lax SJ, Harvey J, Axon E, Howells L, Santer M, Ridd MJ, Lawton S, Langan S, Roberts A, Ahmed A, Muller I, Ming LC, Panda S, Chernyshov P, Carter B, Williams HC, Thomas KS, Chalmers JR |date=March 2022 |title=Strategies for using topical corticosteroids in children and adults with eczema |journal=The Cochrane Database of Systematic Reviews |volume=2022 |issue=3 |pages=CD013356 |doi=10.1002/14651858.CD013356.pub2 |pmc=8916090 |pmid=35275399 |collaboration=Cochrane Skin Group}}</ref>

==Adverse effects==

The nasal spray and oral inhaler formulation have fewer corticosteroid side effects than the tablet formulation because they limit systemic (blood) absorption.<ref name="Flonase Allergy Relief FDA label">{{cite web | title=Flonase Allergy Relief- fluticasone propionate spray, metered | website=DailyMed | date=30 May 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b6134ba0-b70a-4eac-9a82-cef64b242c1d | access-date=31 January 2020 | archive-date=2 December 2020 | archive-url=https://web.archive.org/web/20201202035458/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b6134ba0-b70a-4eac-9a82-cef64b242c1d | url-status=live }}</ref> However, systemic absorption is not negligible even with correct administration.<ref name="Flonase Allergy Relief FDA label"/>{{Specify|date=October 2023}} Using the spray or inhaler at higher than recommended doses or with other corticosteroids can increase the risk for serious, systemic corticosteroid induced side effects.<ref name="Flonase Allergy Relief FDA label"/><ref name="Flovent Diskus FDA label">{{cite web | title=Flovent Diskus- fluticasone propionate powder, metered | website=DailyMed | date=7 January 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=001f22f8-a83d-495f-9196-d0264ef4d76e | access-date=31 January 2020 | archive-date=7 December 2019 | archive-url=https://web.archive.org/web/20191207063245/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=001f22f8-a83d-495f-9196-d0264ef4d76e | url-status=live }}</ref> These side effects include weakened [[immune system]], increased risk of [[systemic infection]]s, [[osteoporosis]], and elevated [[Intraocular pressure|pressure in the eyes]].<ref>{{cite web|url=http://www.mayoclinic.org/steroids/art-20045692?pg=2|title=Prednisone and other corticosteroids: Balance the risks and benefits|website=[[Mayo Clinic]]|access-date=4 March 2018|archive-date=25 May 2017|archive-url=https://web.archive.org/web/20170525083832/http://www.mayoclinic.org/steroids/art-20045692?pg=2|url-status=live}}</ref>

===Nasal spray===

[[File:Flonase.jpg|thumb|left|upright=0.4|Flonase brand nasal spray]]

Common side effects may include nasal irritation (burning, stinging, bleeding), headache, upset stomach (nausea, vomiting), and diarrhea. Rare side effects include infection (evidenced by, for example, fever, sore throat, and cough), [[glaucoma|vision problems]], [[angioedema|severe swelling]], hoarse voice, and [[anaphylaxis|difficulty breathing or swallowing]].<ref name="Medline" /><ref name=AHFS2019ENT/><ref name="Flonase Allergy Relief FDA label"/>

===Inhaled===

Common side effects may include upper respiratory tract infection, throat irritation, [[oral candidiasis|thrush]], cough, and headache. Rare side effects include bruising, swelling of the face/neck, depression, tiredness, and shortness of breath.<ref>{{cite web | work = AHFS Consumer Medication Information [Internet]. | location = Bethesda (MD) | publisher = American Society of Health-System Pharmacists, Inc. | orig-year = 2008 | title = Fluticasone Oral Inhalation | date = 1 September 2010 | access-date = 2 November 2014 | url = https://www.nlm.nih.gov/medlineplus/druginfo/meds/a601056.html | archive-date = 3 November 2014 | archive-url = https://web.archive.org/web/20141103051700/http://www.nlm.nih.gov/medlineplus/druginfo/meds/a601056.html | url-status = live }}</ref><ref name=AHFS2019Inhaled/><ref name="Flovent Diskus FDA label"/>

==Pharmacology==

Fluticasone propionate is a highly selective [[agonist]] at the [[glucocorticoid receptor]] with negligible activity at [[Androgen receptor|androgen]], [[Estrogen receptor|estrogen]], or [[mineralocorticoid receptor]]s,<ref name="Cutivate FDA label" /> thereby producing [[anti-inflammatory]] and [[vasoconstriction]] effects. It has been shown to have a wide range of inhibitory effects on multiple cell types (e.g. [[mast cell]], [[eosinophil]], [[neutrophil]], [[macrophage]]s, and [[lymphocyte]]s) and mediators (e.g. [[histamine]], [[eicosanoid]]s, [[leukotriene]]s, and [[cytokine]]s) involved in [[inflammation]]. Fluticasone propionate is stated to exert a topical effect on the lungs without significant systemic effects at usual doses, due to its low systemic [[bioavailability]].<ref name="Medline">{{Cite web |title=Fluticasone Nasal Spray: MedlinePlus Drug Information |url=https://medlineplus.gov/druginfo/meds/a695002.html |access-date=14 October 2023 |website=MedlinePlus |archive-date=5 September 2023 |archive-url=https://web.archive.org/web/20230905024124/https://medlineplus.gov/druginfo/meds/a695002.html |url-status=live }}</ref>

==Interactions==

Fluticasone propionate is broken down by [[CYP3A4]] ([[cytochrome P450]] 3A4), and has been shown to interact with strong CYP3A4 inhibitors such as [[ritonavir]] and [[ketoconazole]].<ref name="Flonase Allergy Relief FDA label"/><ref name="Flovent Diskus FDA label"/> Coadministration of ritonavir and fluticasone may lead to increased levels of fluticasone in the body, which may lead to [[Cushing's Syndrome]] and [[adrenal insufficiency]].<ref name="pmid18459946">{{cite journal | vauthors = Foisy MM, Yakiwchuk EM, Chiu I, Singh AE | title = Adrenal suppression and Cushing's syndrome secondary to an interaction between ritonavir and fluticasone: a review of the literature | journal = HIV Medicine | volume = 9 | issue = 6 | pages = 389–96 | date = July 2008 | pmid = 18459946 | doi = 10.1111/j.1468-1293.2008.00579.x | s2cid = 40502127 }}</ref> [[Ketoconazole]], an [[antifungal drug]], has been shown to increase fluticasone concentration leading to systemic corticosteroid side effects.<ref name="Flonase Allergy Relief FDA label"/><ref name="Flovent Diskus FDA label"/>

== Society and culture ==

In 2024, [[GSK plc]] removed Flovent from the market and replaced it with an authorized generic.<ref>{{cite news |url=https://www.npr.org/sections/health-shots/2023/12/30/1222224197/a-popular-asthma-inhaler-is-leaving-pharmacy-shelves-heres-what-you-need-to-know |title=A popular asthma inhaler is leaving pharmacy shelves. Here's what you need to know |date=30 December 2023 |author=Sydney Lupkin |publisher=NPR}}</ref><ref>{{cite web | last=Tirrell | first=Meg | title='A huge shock to the system': Doctors warn about asthma inhaler switch coming in January | website=CNN | date=28 December 2023 | url=https://www.cnn.com/2023/12/28/health/asthma-inhaler-generic-switch/index.html | access-date=10 January 2024}}</ref>

==References==

{{Reflist}}

==External links==

* {{cite web | title=Fluticasone Topical | website=MedlinePlus | url=https://medlineplus.gov/druginfo/meds/a601057.html }}

{{Glucocorticoids}}

{{Nasal preparations}}

{{Asthma and copd_rx}}

{{Glucocorticoidics}}

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