Fluticasone

drugbox
IUPAC_name = "S"-(fluoromethyl) (6"S",8"S",9"R",10"S",11"S",13"S",14"S",16"R",17"R")-
6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-
6,7,8,11,12,14,15,16-octahydrocyclopenta ["a"]
phenanthrene-17-carbothioate

---

CAS_number = 80474-14-2
ATC_prefix = D07
ATC_suffix = AC17
ATC_supplemental = & ATC|D07|AC04 (topical)
*ATC|R01|AD08 (nasal)
*ATC|R03|BA05 (inhaled)
*ATC|R01|AD12 (furoate)
PubChem = 5311101
DrugBank = APRD00065
C=22 | H=27 | F=3 | O=4 | S=1
molecular_weight = 444.508 g/mol
smiles = FCSC(=O) [C@@] 1(OC(=O)CC) [C@H] (C)C [C@H] 2 [C@@H] 3C [C@H] (F)C4=CC(=O)C=C [C@] 4(C) [C@@] 3(F) [C@@H] (O)C [C@] 12C
bioavailability = 0.51% (Intranasal)
protein_bound = 91%
metabolism = Intranasal
Hepatic (CYP3A4-mediated)
elimination_half-life = 10 hours
excretion = Renal
pregnancy_AU =
pregnancy_US =
pregnancy_category = C for Intranasal and Inhaled
legal_AU =
legal_CA =
legal_UK = POM
legal_US = Rx-only
legal_status =
routes_of_administration = Intranasal, Inhaled, Topical Cream or Ointment

Fluticasone is a potent synthetic corticosteroid often prescribed as treatment for asthma and allergic rhinitis.

The related fluticasone propionate is marketed with the brand names Flixotide (UK) for asthma and Flixonase (UK) for allergic rhinitis by Allen & Hanburys. In the US, it is marketed for asthma as Flovent, and allergic rhinitis as Flonase, by GlaxoSmithKline. GlaxoSmithKline also markets a combination of fluticasone and salmeterol as Advair (US) or Seretide (UK).

The related fluticasone furoate is marketed by GlaxoSmithKline as Veramyst (US) for the treatment of allergic rhinitis.

It is also used as a cream or ointment for the treatment of eczema and psoriasis (Cutivate or Flutivate).

Mechanism of action

Inflammation is recognized as an important component in the pathogenesis of asthma. Glucocorticoids have been shown to inhibit multiple cell types (e.g., mast cells, eosinophils, basophils, lymphocytes, macrophages, and neutrophils) and mediate production or secretion (e.g., histamine, eicosanoids, leukotrienes, and cytokines) involved in the asthmatic response. These anti-inflammatory actions of glucocorticoids may contribute to their efficacy in asthma. Typically, however, the action on the cells affected requires several days. Therefore, inhaled steroids are not used for immediate relief of asthma, but instead as preventive and maintenance therapy.

Nasal spray

Dosage

*Adults: The recommended dosage for adults is 110 micrograms (two inhalations) once daily. This may be increased to maximum of twice daily use if required. When control is achieved dose is reduced to 50 micrograms (one spray) daily.
*Adolescents and children: The recommended dosage for children (4 years of age or older in US, but only from 12 years in UK) is 50 micrograms (one spray) into each nostril once daily. This may be increased to maximum of twice daily use if required.

Flonase patent issues

GlaxoSmithKline's patent on Flonase expired in May 2004. The Food and Drug Administration (FDA) approved the sale of a generic version of Flonase on February 22, 2006. On February 23, 2006, GlaxoSmithKline (GSK) was able to obtain a temporary 10-day restraining order from a federal judge in Baltimore blocking the shipment and sales of the approved generic versions of Flonase. The restraining order lasted until March 6, 2006. The basis of the complaint by GSK was that the FDA failed to follow its own regulations in approving the generics and failed to apply the same quality standards for the generic version as it did for Flonase. GSK made these arguments in petitions filed with the FDA, but the FDA rejected those petitions. The Maryland District Court denied the request by GSK to extend the ban on Flonase generics beyond March 6, 2006, and GSK released a statement that they would not appeal the ruling. [http://www.medicalnewstoday.com/medicalnews.php?newsid=39333] The ruling meant that sales of generic versions of Flonase could proceed.

References

* [http://www.gsk.com/ControllerServlet?appId=4&pageId=402&newsid=754 GSK's official statement on Flonase generic]
* [http://www.rxlist.com/cgi/generic/flutic_ids.htm RxList The Internet Drug Index]
* BNF 45 March 2003

Clinical trials

"This listing is NOT complete and should NOT be construed as support for treatment decisions." See also [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?termClinical=fluticasone&precision=specificity&strategy=therapy&filters=&orig_db=PubMed&db=PubMed&cmd=Search&term=%28fluticasone%29+AND+%28randomized+controlled+trial%5BPublication+Type%5D+OR+%28randomized%5BTitle%2FAbstract%5D+AND+controlled%5BTitle%2FAbstract%5D+AND+trial%5BTitle%2FAbstract%5D%29%29 PubMed clinical manuscripts referring to fluticasone]
*
*::"both support a positive outcome for use of fluticasone in patients with chronic obstructive pulmonary disease, also referred to as COPD"

External links

* [http://www.flixonase.co.uk Flixonase Official Website]
* [http://www.flonase.com Flonase Official Website]
* [http://www.veramyst.com Veramyst Official Website]
* [http://www.gw-flovent.com Flovent Official Website]
* [http://www.advair.com Advair Official Website]
* [http://www.fluticasone.com fluticasone Official Website]