Chemistry:Fluticasone propionate

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Short description: Medication
Fluticasone propionate
Fluticasone propionate.svg
Fluticasone-propionate-3D-bs-17.png
Clinical data
Trade namesFlovent, Flixotide, Flonase, others
AHFS/Drugs.comMonograph
MedlinePlusa695002
License data
Pregnancy
category
Routes of
administration		Intranasal,[2] inhalation,[3] topical[4]
Drug classSteroids and steroid derivatives
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability0.51% (Intranasal)
Protein binding91%
MetabolismIntranasal
Liver (CYP3A4-mediated)
Elimination half-life10 hours
ExcretionKidney
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC25H31F3O5S
Molar mass500.57 g·mol−1
3D model (JSmol)
  (verify)

Fluticasone propionate, sold under the brand names Flovent and Flonase among others, is a steroid medication.[6] When inhaled it is used for the long term management of asthma and COPD.[6] In the nose it is used for hay fever and nasal polyps.[7][8] It can also be used for mouth ulcers.[9] It works by decreasing inflammation.[6]

Common side effects when inhaled include upper respiratory tract infections, sinusitis, thrush, and cough.[6] Common side effects when used in the nose include nosebleeding and sore throat.[7]

Fluticasone propionate was patented in 1980, and approved for medical use in 1990.[10] It is available as a generic medication.[8] In 2021, fluticasone was the 23rd most commonly prescribed medication in the United States, with more than 25 million prescriptions.[11][12]

Medical uses

Fluticasone propionate is used by powder or aerosol inhalation for the prophylaxis of asthma.[3][6] The nasal spray is used for prevention and treatment of allergic rhinitis.[2] Nasal drops are used in the treatment of nasal polyps. The nasal spray can also be used in the mouth for mouth ulcers.[9]

Fluticasone propionate in a topical form can be used to treat skin conditions such as eczema, psoriasis, and rashes.[13][14]

Adverse effects

The nasal spray and oral inhaler formulation have fewer corticosteroid side effects than the tablet formulation because they limit systemic (blood) absorption.[2] However, systemic absorption is not negligible even with correct administration.[2][specify] 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.[2][3] These side effects include weakened immune system, increased risk of systemic infections, osteoporosis, and elevated pressure in the eyes.[15]

Nasal spray

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), vision problems, severe swelling, hoarse voice, and difficulty breathing or swallowing.[16][7][2]

Inhaled

Common side effects may include upper respiratory tract infection, throat irritation, thrush, cough, and headache. Rare side effects include bruising, swelling of the face/neck, depression, tiredness, and shortness of breath.[17][6][3]

Pharmacology

Fluticasone propionate is a highly selective agonist at the glucocorticoid receptor with negligible activity at androgen, estrogen, or mineralocorticoid receptors,[4] 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, macrophages, and lymphocytes) and mediators (e.g. histamine, eicosanoids, leukotrienes, and cytokines) 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.[16]

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.[2][3] 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.[18] Ketoconazole, an antifungal drug, has been shown to increase fluticasone concentration leading to systemic corticosteroid side effects.[2][3]

Society and culture

In 2024, GSK plc removed Flovent from the market and replaced it with an authorized generic.[19][20]

References

  1. ↑ "Fluticasone Use During Pregnancy". 9 January 2019. https://www.drugs.com/pregnancy/fluticasone.html. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 "Flonase Allergy Relief- fluticasone propionate spray, metered". 30 May 2019. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b6134ba0-b70a-4eac-9a82-cef64b242c1d. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "Flovent Diskus- fluticasone propionate powder, metered". 7 January 2019. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=001f22f8-a83d-495f-9196-d0264ef4d76e. 
  4. ↑ 4.0 4.1 4.2 "Cutivate- fluticasone propionate lotion". 8 August 2018. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cc79e200-ce69-4ffd-be5b-8c1a6bb88c5c. 
  5. ↑ "Flixonase Aqueous Nasal Spray - Summary of Product Characteristics (SmPC)". 25 October 2019. https://www.medicines.org.uk/emc/product/845/smpc. 
  6. ↑ 6.0 6.1 6.2 6.3 6.4 6.5 "Fluticasone Propionate Monograph for Professionals". American Society of Health-System Pharmacists. https://www.drugs.com/monograph/fluticasone-propionate.html. 
  7. ↑ 7.0 7.1 7.2 "Fluticasone Propionate eent Monograph for Professionals". American Society of Health-System Pharmacists. https://www.drugs.com/monograph/fluticasone-propionate-eent.html. 
  8. ↑ 8.0 8.1 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 262, 1172. ISBN 9780857113382. 
  9. ↑ 9.0 9.1 "Flixonase aqueous spray". June 2018. https://publicdocuments.sth.nhs.uk/pil2057.pdf. 
  10. ↑ Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 487. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA487. Retrieved 19 September 2020. 
  11. ↑ "The Top 300 of 2021". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  12. ↑ "Fluticasone - Drug Usage Statistics". https://clincalc.com/DrugStats/Drugs/Fluticasone. 
  13. ↑ "Drugs & Medications" (in en). https://www.webmd.com/drugs/2/drug-8786/fluticasone-propionate-topical/details. 
  14. ↑ "Strategies for using topical corticosteroids in children and adults with eczema". The Cochrane Database of Systematic Reviews 2022 (3): CD013356. March 2022. doi:10.1002/14651858.CD013356.pub2. PMID 35275399. 
  15. ↑ "Prednisone and other corticosteroids: Balance the risks and benefits". http://www.mayoclinic.org/steroids/art-20045692?pg=2. 
  16. ↑ 16.0 16.1 "Fluticasone Nasal Spray: MedlinePlus Drug Information". https://medlineplus.gov/druginfo/meds/a695002.html. 
  17. ↑ "Fluticasone Oral Inhalation". AHFS Consumer Medication Information [Internet].. Bethesda (MD): American Society of Health-System Pharmacists, Inc.. 1 September 2010. https://www.nlm.nih.gov/medlineplus/druginfo/meds/a601056.html. 
  18. ↑ "Adrenal suppression and Cushing's syndrome secondary to an interaction between ritonavir and fluticasone: a review of the literature". HIV Medicine 9 (6): 389–96. July 2008. doi:10.1111/j.1468-1293.2008.00579.x. PMID 18459946. 
  19. ↑ Sydney Lupkin (30 December 2023). "A popular asthma inhaler is leaving pharmacy shelves. Here's what you need to know". NPR. 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. 
  20. ↑ Tirrell, Meg (28 December 2023). "'A huge shock to the system': Doctors warn about asthma inhaler switch coming in January". https://www.cnn.com/2023/12/28/health/asthma-inhaler-generic-switch/index.html. 

External links



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