Fluticasone propionate

Last updated

Fluticasone propionate
Fluticasone propionate.svg
Fluticasone-propionate-3D-bs-17.png
Clinical data
Trade names Flovent, Flixotide, Flonase, others
AHFS/Drugs.com Monograph
MedlinePlus a695002
License data
Pregnancy
category
Routes of
administration
Intranasal, [2] inhalation, [3] topical [4]
Drug class Steroids and steroid derivatives
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 0.51% (Intranasal)
Protein binding 91%
Metabolism Intranasal
Liver (CYP3A4-mediated)
Elimination half-life 10 hours
Excretion Kidney
Identifiers
  • S-(fluoromethyl)-6α,9-difluoro-11β, 17-dihydroxy-16α-methyl-3-oxoandrosta-1, 4-diene-17β-carbothioate, 17-propanoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.129.097 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C25H31F3O5S
Molar mass 500.57 g·mol−1
3D model (JSmol)
  • CCC(=O)OC1(C(CC2C1(CC(C3(C2CC(C4=CC(=O)C=CC43C)F)F)O)C)C)C(=O)SCF
  • InChI=1S/C25H31F3O5S/c1-5-20(31)33-25(21(32)34-12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15+,16+,18+,19+,22+,23+,24+,25+/m1/s1 Yes check.svgY
  • Key:WMWTYOKRWGGJOA-CENSZEJFSA-N Yes check.svgY
   (verify)

Fluticasone propionate, sold under the brand names Flovent and Flonase among others, is a glucocorticoid steroid medication. [8] When inhaled it is used for the long term management of asthma and COPD. [8] In the nose it is used for hay fever and nasal polyps. [9] [10] It can also be used for mouth ulcers. [11] It works by decreasing inflammation.

Contents

Common side effects when inhaled include upper respiratory tract infections, sinusitis, thrush, and cough. [8] Common side effects when used in the nose include nosebleeding and sore throat. [9] Unlike fluticasone furoate, which is approved in children as young as two years of age when used for allergies, fluticasone propionate is only approved for children four years and older. [12] [13]

Fluticasone propionate was patented in 1980, and approved for medical use in 1990. [14] It is available as a generic medication. [10] In 2022, fluticasone was the 25th most commonly prescribed medication in the United States, with more than 22 million prescriptions. [15] [16]

Medical uses

Fluticasone propionate is used by powder or aerosol inhalation for the prophylaxis of asthma. [3] [8] 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. [11]

Fluticasone propionate in a topical form can be used to treat skin conditions such as eczema, psoriasis, and rashes. [17] [18]

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. [19]

Nasal spray

Flonase brand nasal spray Flonase.jpg
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. [20] [9] [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. [21] [8] [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. [20]

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. [22] 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. [23] [24]

Related Research Articles

<span class="mw-page-title-main">Corticosteroid</span> Class of steroid hormones

Corticosteroids are a class of steroid hormones that are produced in the adrenal cortex of vertebrates, as well as the synthetic analogues of these hormones. Two main classes of corticosteroids, glucocorticoids and mineralocorticoids, are involved in a wide range of physiological processes, including stress response, immune response, and regulation of inflammation, carbohydrate metabolism, protein catabolism, blood electrolyte levels, and behavior.

A decongestant, or nasal decongestant, is a type of pharmaceutical drug that is used to relieve nasal congestion in the upper respiratory tract. The active ingredient in most decongestants is either pseudoephedrine or phenylephrine. Intranasal corticosteroids can also be used as decongestants and antihistamines can be used to alleviate runny nose, nasal itch, and sneezing.

<span class="mw-page-title-main">Fluticasone</span> Chemical compound

Fluticasone is a manufactured glucocorticoid used to treat nasal symptoms. Both the esters, fluticasone propionate and fluticasone furoate, are also used as topical anti-inflammatories and inhaled corticosteroids, and are used much more commonly in comparison.

<span class="mw-page-title-main">Ipratropium bromide</span> Type of anticholinergic

Ipratropium bromide, sold under the trade name Atrovent among others, is a type of anticholinergic medication which is applied by different routes: inhaler, nebulizer, or nasal spray, for different reasons.

<span class="mw-page-title-main">Fluticasone/salmeterol</span> Formulation used in the management of asthma and chronic obstructive pulmonary disease

Fluticasone/salmeterol, sold under the brand name Advair among others, is a fixed-dose combination medication containing fluticasone propionate, an inhaled corticosteroid; and salmeterol, a long-acting beta2‑adrenergic agonist. It is used in the management of asthma and chronic obstructive pulmonary disease (COPD). It is used by inhaling the medication into the lungs.

<span class="mw-page-title-main">Triamcinolone</span> Steroid medication

Triamcinolone is a glucocorticoid used to treat certain skin diseases, allergies, and rheumatic disorders among others. It is also used to prevent worsening of asthma and COPD. It can be taken in various ways including by mouth, injection into a muscle, and inhalation.

<span class="mw-page-title-main">Nasal spray</span> Spray that delivers medications locally in the nasal cavities or systemically

Nasal sprays are used to deliver medications locally in the nasal cavities or systemically. They are used locally for conditions such as nasal congestion and allergic rhinitis. In some situations, the nasal delivery route is preferred for systemic therapy because it provides an agreeable alternative to injection or pills. Substances can be assimilated extremely quickly and directly through the nose. Many pharmaceutical drugs exist as nasal sprays for systemic administration. Other applications include hormone replacement therapy, treatment of Alzheimer's disease and Parkinson's disease. Nasal sprays are seen as a more efficient way of transporting drugs with potential use in crossing the blood–brain barrier.

<span class="mw-page-title-main">Salmeterol</span> Chemical compound

Salmeterol is a long-acting β2 adrenergic receptor agonist (LABA) used in the maintenance and prevention of asthma symptoms and maintenance of chronic obstructive pulmonary disease (COPD) symptoms. Symptoms of bronchospasm include shortness of breath, wheezing, coughing and chest tightness. It is also used to prevent breathing difficulties during exercise.

<span class="mw-page-title-main">Budesonide/formoterol</span> Medication for asthma & chronic obstructive pulmonary disease

Budesonide/formoterol, sold under the brand name Symbicort among others, is a fixed-dose combination medication used in the management of asthma or chronic obstructive pulmonary disease (COPD). It contains budesonide, a steroid; and formoterol, a long-acting β2-agonist (LABA). The product monograph does not support its use for sudden worsening or treatment of active bronchospasm. However, a 2020 review of the literature does support such use. It is used by breathing in the medication.

<span class="mw-page-title-main">Formoterol</span> Long-acting bronchiodilator

Formoterol, also known as eformoterol, is a 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 compared to short-acting β2 agonists such as salbutamol (albuterol), which are effective for 4 h to 6 h. Formoterol has a relatively rapid onset of action compared to other LABAs, and is effective within 2-3 minutes. The 2022 Global Initiative for Asthma report 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 is still recommended.

<span class="mw-page-title-main">Olopatadine</span> Chemical compound

Olopatadine, sold under the brand name Patanol among others, is an antihistamine medication used to decrease the symptoms of allergic conjunctivitis and allergic rhinitis. It is used as eye drops or as a nasal spray. The eye drops generally result in an improvement within half an hour.

Beta<sub>2</sub>-adrenergic agonist Compounds that bind to and activate adrenergic beta-2 receptors

Beta2-adrenergic agonists, also known as adrenergic β2 receptor agonists, are a class of drugs that act on the β2 adrenergic receptor. Like other β adrenergic agonists, they cause smooth muscle relaxation. β2 adrenergic agonists' effects on smooth muscle cause dilation of bronchial passages, vasodilation in muscle and liver, relaxation of uterine muscle, and release of insulin. They are primarily used to treat asthma and other pulmonary disorders. Bronchodilators are considered an important treatment regime for chronic obstructive pulmonary disease (COPD) and are usually used in combination with short acting medications and long acting medications in a combined inhaler.

<span class="mw-page-title-main">Beclometasone</span> Chemical compound

Beclometasone or beclomethasone, also known as beclomethasone dipropionate, and sold under the brand name Qvar among others, is a steroid medication. It is available as an inhaler, cream, pills, and nasal spray. The inhaled form is used in the long-term management of asthma. The cream may be used for dermatitis and psoriasis. The pills have been used to treat ulcerative colitis. The nasal spray is used to treat allergic rhinitis and nasal polyps.

<span class="mw-page-title-main">Mometasone</span> Steroid medication

Mometasone, also known as mometasone y 3 s, is a steroid medication used to treat certain skin conditions, hay fever, and asthma. Specifically it is used to prevent rather than treat asthma attacks. It can be applied to the skin, inhaled, or used in the nose. Mometasone furoate, not mometasone, is used in medical products.

Topical steroids are the topical forms of corticosteroids. Topical steroids are the most commonly prescribed topical medications for the treatment of rash and eczema. Topical steroids have anti-inflammatory properties and are classified based on their skin vasoconstrictive abilities. There are numerous topical steroid products. All the preparations in each class have the same anti-inflammatory properties but essentially differ in base and price.

<span class="mw-page-title-main">Fluticasone furoate</span> Corticosteroid

Fluticasone furoate, sold under the brand name Flonase Sensimist among others, is a corticosteroid for the treatment of non-allergic and allergic rhinitis administered by a nasal spray. It is also available as an inhaled corticosteroid to help prevent and control symptoms of asthma. It is derived from cortisol. Unlike fluticasone propionate, which is only approved for children four years and older, fluticasone furoate is approved in children as young as two years of age when used for allergies.

<span class="mw-page-title-main">Budesonide</span> Type of corticosteroid medication

Budesonide, sold under the brand name Pulmicort, among others, is a steroid medication. It is available as an inhaler, nebulization solution, pill, nasal spray, and rectal forms. The inhaled form is used in the long-term management of asthma and chronic obstructive pulmonary disease (COPD). The nasal spray is used for allergic rhinitis and nasal polyps. Modified-release pills or capsules and rectal forms may be used for inflammatory bowel disease including Crohn's disease, ulcerative colitis, and microscopic colitis.

<span class="mw-page-title-main">Fluticasone furoate/vilanterol</span> Pharmaceutical drug formulation

Fluticasone furoate/vilanterol, sold under the brand name Breo Ellipta among others, is a combination medication for the treatment of chronic obstructive pulmonary disease (COPD) and asthma. It contains fluticasone furoate, an inhaled corticosteroid, and vilanterol, an ultra-long-acting β2 agonist (ultra-LABA).

Fluticasone furoate/umeclidinium bromide/vilanterol, sold under the brand name Trelegy Ellipta among others, is a fixed-dose combination inhaled medication that is used for the maintenance treatment of chronic obstructive pulmonary disease (COPD). The medications work in different ways: fluticasone furoate is an inhaled corticosteroid (ICS), umeclidinium is a long-acting muscarinic antagonist (LAMA), and vilanterol is a long-acting beta-agonist (LABA).

Indacaterol/glycopyrronium bromide/mometasone, sold under the brand name Enerzair Breezhaler among others, is an inhalable fixed-dose combination medication for the treatment of asthma. It contains indacaterol as acetate, glycopyrronium bromide, and mometasone furoate.

References

  1. "Fluticasone Use During Pregnancy". Drugs.com. 9 January 2019. Archived from the original on 26 March 2019. Retrieved 31 January 2020.
  2. 1 2 3 4 5 6 7 8 "Flonase Allergy Relief- fluticasone propionate spray, metered". DailyMed. 30 May 2019. Archived from the original on 2 December 2020. Retrieved 31 January 2020.
  3. 1 2 3 4 5 6 "Flovent Diskus- fluticasone propionate powder, metered". DailyMed. 7 January 2019. Archived from the original on 7 December 2019. Retrieved 31 January 2020.
  4. 1 2 3 "Cutivate- fluticasone propionate lotion". DailyMed. 8 August 2018. Archived from the original on 20 February 2022. Retrieved 19 February 2022.
  5. "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  6. "Respiratory health". Health Canada . 9 May 2018. Retrieved 13 April 2024.
  7. "Flixonase Aqueous Nasal Spray - Summary of Product Characteristics (SmPC)". (emc). 25 October 2019. Archived from the original on 31 January 2020. Retrieved 31 January 2020.
  8. 1 2 3 4 5 "Fluticasone Propionate Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 28 February 2019. Retrieved 27 February 2019.
  9. 1 2 3 "Fluticasone Propionate eent Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 28 February 2019. Retrieved 27 February 2019.
  10. 1 2 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 262, 1172. ISBN   9780857113382.
  11. 1 2 "Flixonase aqueous spray" (PDF). Sheffield Teaching Hospitals. June 2018. Archived from the original (PDF) on 25 September 2019. Retrieved 31 January 2020.
  12. "Flonase Sensimist Allergy Relief- fluticasone furoate spray, metered". DailyMed. 30 May 2019. Archived from the original on 2 December 2020. Retrieved 4 February 2020.
  13. "Veramyst- fluticasone furoate spray, metered". DailyMed. 1 March 2010. Archived from the original on 5 February 2020. Retrieved 4 February 2020.
  14. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 487. ISBN   9783527607495. Archived from the original on 28 November 2023. Retrieved 19 September 2020.
  15. "The Top 300 of 2022". clincalc.com. Retrieved 19 August 2024.
  16. "Fluticasone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  17. "Drugs & Medications". www.webmd.com. Archived from the original on 22 October 2020. Retrieved 13 April 2020.
  18. Lax SJ, Harvey J, Axon E, Howells L, Santer M, Ridd MJ, et al. (Cochrane Skin Group) (March 2022). "Strategies for using topical corticosteroids in children and adults with eczema". The Cochrane Database of Systematic Reviews. 2022 (3): CD013356. doi:10.1002/14651858.CD013356.pub2. PMC   8916090 . PMID   35275399.
  19. "Prednisone and other corticosteroids: Balance the risks and benefits". Mayo Clinic . Archived from the original on 25 May 2017. Retrieved 4 March 2018.
  20. 1 2 "Fluticasone Nasal Spray: MedlinePlus Drug Information". MedlinePlus. Archived from the original on 5 September 2023. Retrieved 14 October 2023.
  21. "Fluticasone Oral Inhalation". AHFS Consumer Medication Information [Internet]. Bethesda (MD): American Society of Health-System Pharmacists, Inc. 1 September 2010 [2008]. Archived from the original on 3 November 2014. Retrieved 2 November 2014.
  22. Foisy MM, Yakiwchuk EM, Chiu I, Singh AE (July 2008). "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. doi:10.1111/j.1468-1293.2008.00579.x. PMID   18459946. S2CID   40502127.
  23. Sydney Lupkin (30 December 2023). "A popular asthma inhaler is leaving pharmacy shelves. Here's what you need to know". NPR.
  24. Tirrell M (28 December 2023). "'A huge shock to the system': Doctors warn about asthma inhaler switch coming in January". CNN. Retrieved 10 January 2024.