Fluticasone propionate

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 for Intranasal and Inhaled
Legal status	P (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
ATC code	D07AC17 & D07AC04 (topical)
PubChem	CID 444036
DrugBank	APRD00065
ChemSpider	392059 Y
UNII	O2GMZ0LF5W Y
ChEBI	CHEBI:31441 Y
ChEMBL	CHEMBL1473 Y
Chemical data
Formula	C25H31F3O5S
Mol. mass	500.57 g/mol
SMILES	eMolecules & PubChem
InChI 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 Y Key:WMWTYOKRWGGJOA-CENSZEJFSA-N Y
Y(what is this?)  propionate (verify)

Fluticasone propionate is a synthetic corticosteroid derived from fluticasone used to treat asthma and allergic rhinitis (hay fever). 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 (EU, South Africa, Israel and Brazil) for allergic rhinitis (hay fever), as well as a combination of fluticasone and salmeterol as Advair (USA and Canada) or Seretide (EU). Teva markets fluticasone propionate as Nasofan in Italy.

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

Flonase patent issues

Fluticasone propionate metered dose inhaler.

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.^[1] The ruling meant that sales of generic versions of Flonase could proceed.

Side effects

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.^[2]

Side effects associated with the nostril spray version include headache, throat infection, nasal irritation, sneezing, cough, nausea, vomiting, nosebleeds, skin rash, itching, facial swelling, and anaphylaxis. It has also been associated with growth suppression in children.^[3]

See also

• Fluticasone
• Fluticasone furoate
• Anti-inflammatory uses of glucocorticoids

References

1. ^ Medical News Today
2. ^ FDA
3. ^ Medicinenet.com