Fluticasone propionate

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Fluticasone propionate
Systematic (IUPAC) name
S-(fluoromethyl)-6α,9-difluoro-11β, 17-dihydroxy-16α-methyl-3-oxoandrosta-1, 4-diene-17β-carbothioate, 17-propanoate
Clinical data
AHFS/Drugs.com monograph
Pregnancy cat. C (US) C for Intranasal and Inhaled
Legal status POM (UK) Rx Only (US)
Routes Intranasal, Inhaled, Topical Cream or Ointment
Pharmacokinetic data
Bioavailability 0.51% (Intranasal)
Protein binding 91%
Metabolism Intranasal
Hepatic (CYP3A4-mediated)
Half-life 10 hours
Excretion Renal
Identifiers
CAS number 80474-14-2 YesY
ATC code D07AC17 & D07AC04 (topical)
PubChem CID 444036
DrugBank DB00588
ChemSpider 392059 YesY
UNII O2GMZ0LF5W YesY
ChEBI CHEBI:31441 YesY
ChEMBL CHEMBL1473 YesY
Chemical data
Formula C25H31F3O5S 
Mol. mass 500.57 g/mol
 YesY (what is this?)  (verify)
FloVent HFA inhaler

Fluticasone propionate is a corticosteroid derived from fluticasone used to treat asthma and allergic rhinitis. It is also used to treat eosinophilic esophagitis.

GlaxoSmithKline currently markets fluticasone propionate as Flovent (USA and Canada) and Flixotide (EU) for asthma, and as Flonase (USA and Canada), Flixonase (Australia, Brazil, EU, Morocco, India, Israel, South Africa, and South Korea) and Pirinase (UK) for allergic rhinitis (hay fever), as well as a combination of fluticasone and salmeterol as Advair (USA and Canada) or Seretide[1] (EU). In India it is also marketed by Intas under the trade name 'Ezicas'.
Ezicas
Teva markets fluticasone propionate as Nasofan in Italy. It is available as Fluticone in India. It is also available as a cream (marketed as Cutivate or Flutivate) for the treatment of eczema and psoriasis.

Flonase patent issues

(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.[2] The ruling meant that sales of generic versions of Flonase could proceed.

Monopoly class action lawsuit settlement

MEDICAL MUTUAL OF OHIO brought suit against GSK for conspiring to keep generic Flonase off the market. A class action lawsuit settlement with a “Total Settlement Amount” of $45 million was reached. Both consumers and insurance companies like the plaintiff had until August 15, 2013 to file a claim.[3]

Chemistry and Side effects

Fluticasone propionate is a synthetic trifluorinated glucocorticoid. It is highly lipophilic (logp octanol/water 3.69).[4]

In studies the topical drug has been associated with burning, stinging, skin irritation, blisters, dryness, skin infection, infected eczema, viral warts, impetigo, atopic dermatitis, pruritus, exacerbation of pruritus, exacerbation of eczema, erythema, and folliculitis.[5]

There are also numerous side effects associated with the oral version of this medication including headache, stuffy or runny nose, difficulty speaking, sore or irritated throat and painful white patches in the mouth or throat.[6]

Candidiasis of mouth and throat is reported as a "very common" side effect indicating that it occurs with a frequency greater than 1 in 10.[7] Hoarseness is "common" indicating a frequency from 1 in 10 to 1 in 100.[7] In both instances rinsing the mouth with water immediately after inhalation is recommended.[7]

Excessive use of corticosteroids, particularly fluticasone propionate, are "the most common cause of hypercortisolemia among all age groups." [8]

While hypercortisolism (excess cortisol) is common during fluticasone propionate inhaler use, hypocortisolism (suppressed cortisol) can be expected as a result of sudden withdrawal from fluticasone propionate.[9]

See also

References

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