Fluticasone propionate
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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 Y |
ATC code |
D07AC17 & D07AC04 (topical) |
PubChem |
CID 444036 |
DrugBank |
DB00588 |
ChemSpider |
392059 Y |
UNII |
O2GMZ0LF5W Y |
ChEBI |
CHEBI:31441 Y |
ChEMBL |
CHEMBL1473 Y |
Chemical data |
Formula |
C25H31F3O5S |
Mol. mass |
500.57 g/mol |
SMILES
- O=C(SCF)[C@]3(OC(=O)CC)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)[C@@H](F)C[C@H]4[C@@H]2C[C@H]3C)C)C
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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
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Y (what is this?) (verify)
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Fluticasone propionate is a 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 (Australia, Brazil, EU, 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'. 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.
Contents
- 1 Flonase patent issues
- 2 Side effects
- 3 See also
- 4 References
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Flonase patent issues [edit]
(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.
Side effects [edit]
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.[3]
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.[4]
See also [edit]
- Fluticasone
- Fluticasone furoate
- Anti-inflammatory uses of glucocorticoids
References [edit]
- ^ Allen & Hanburys. Package Leaflet: Information for the User of Seretide(tm) Evohaler(tm). GSK.
- ^ Medical News Today
- ^ FDA
- ^ Fluticasone Oral Inhalation U.S. National Library of Medicine
Decongestants and other nasal preparations (R01)
|
|
Topical |
Sympathomimetics, plain
|
- Cyclopentamine
- Ephedrine
- Phenylephrine
- Oxymetazoline
- Tetryzoline
- Xylometazoline
- Naphazoline
- Tramazoline
- Metizoline
- Tuaminoheptane
- Fenoxazoline
- Tymazoline
- Epinephrine
|
|
Antiallergic agents,
excluding corticosteroids
|
- histamine antagonists (Levocabastine
- Antazoline
- Thonzylamine)
- mast cell stabilizer (some are also antihistamines) (Cromoglicic acid
- Nedocromil
- Azelastine
- Olopatadine
- Lodoxamide)
|
|
Corticosteroids
|
- Beclometasone
- Prednisolone
- Dexamethasone
- Flunisolide
- Budesonide
- Betamethasone
- Tixocortol
- Fluticasone
- Mometasone furoate
- Triamcinolone
- Ciclesonide
|
|
Other nasal preparations
|
- Cafaminol
- Calcium hexamine thiocyanate
- Retinol
- Ipratropium bromide
- Ritiometan
- Mupirocin
- Hexamidine
- Framycetin
- Hyaluronic acid
- Eucalyptus oil
|
|
|
Systemic use:
Sympathomimetics |
- Phenylpropanolamine
- Pseudoephedrine (+loratadine)
- Phenylephrine
- Phenylpropylamine
|
|
|
anat (n, x, l, c)/phys/devp
|
noco (c, p)/cong/tumr, sysi/epon, injr
|
proc, drug (R1/2/3/5/6/7)
|
|
|
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Drugs for obstructive airway diseases: asthma/COPD (R03)
|
|
Adrenergics, inhalants |
Short acting β2-agonists |
- Bitolterol
- Carbuterol
- Fenoterol
- Pirbuterol
- Procaterol
- Reproterol
- Rimiterol
- Salbutamol#/Levosalbutamol
- Terbutaline
- Tulobuterol
|
|
Long acting β2-agonists (LABA) |
- Arformoterol
- Bambuterol
- Clenbuterol
- Formoterol
- Olodaterol
- Salmeterol
- Ultra LABA: Indacaterol
|
|
other |
- Epinephrine#
- Hexoprenaline
- Isoprenaline (Isoproterenol)
- Orciprenaline (Metaproterenol)
|
|
|
Glucocorticoids |
- Beclometasone#
- Betamethasone
- Budesonide
- Ciclesonide
- Flunisolide
- Fluticasone
- Mometasone
- Triamcinolone
|
|
Anticholinergics/
muscarinic antagonist |
- Aclidinium bromide
- Glycopyrronium bromide
- Ipratropium bromide#
- Oxitropium bromide
- Tiotropium bromide
|
|
Mast cell stabilizers |
|
|
Xanthines |
- Doxofylline
- Enprofylline
- Theobromine
- Theophylline/Aminophylline/Choline theophyllinate
|
|
Eicosanoid inhibition |
Leukotriene antagonists |
- Montelukast
- Pranlukast
- Zafirlukast
|
|
Lipoxygenase inhibitor |
|
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Thromboxane receptor antagonists |
|
|
|
Combination products |
- Budesonide/formoterol
- Fluticasone/salmeterol
- Ipratropium bromide/salbutamol
- Mometasone/formoterol
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
anat (n, x, l, c)/phys/devp
|
noco (c, p)/cong/tumr, sysi/epon, injr
|
proc, drug (R1/2/3/5/6/7)
|
|
|
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Corticosteroids – glucocorticoids and mineralocorticoids (H02)
(also A07EA, C05AA, D07, D10AA, R01AD, R03BA, S01BA, S02B, and S03B)
|
|
Mineralocorticoids
(3-one, 4-ene,
no FG at 16) |
- Pregnenedione: ALDOSTERONE
- 11-DEOXYCORTICOSTERONE
- HALOGENATED AT 9: Fludrocortisone
|
|
Glucocorticoids
(3-one, 4-ene,
11-FG,
17-hydroxy) |
Pregnene
|
|
|
Pregnenedione
(+20-one)
|
- HYDROCORTISONE/CORTISOL# (Hydrocortisone aceponate
- Hydrocortisone buteprate
- Hydrocortisone butyrate)
- Budesonide
- Ciclesonide
- Deflazacort
- Medrysone
- Tixocortol
- HALOGENATED AT 6: Cloprednol
- HALOGENATED, WITH FG AT 16: Halcinonide
|
|
Pregnadiene (+1-ene)
|
- Rimexolone
- HALOGENATED, WITH FG AT 16: Flunisolide
- Triamcinolone
- Amcinonide
- Fluocinolone acetonide (Fluocinonide)
|
|
Pregnadienediol
(+21-hydroxy)
|
- Prednisone (Meprednisone)
- HALOGENATED AT 9: Fluorometholone
- HALOGENATED, WITH FG AT 16: Fluocortolone (Clocortolone
- Diflucortolone
- Fluocortin)
- Desoximetasone
|
|
Pregnadienetriol
(+11-hydroxy)
|
- Prednisolone# (Methylprednisolone
- Methylprednisolone aceponate
- Prednicarbate
- Prednylidene)
- Desonide
- HALOGENATED: Fluprednisolone (Difluprednate
- Fluperolone)
- HALOGENATED, WITH FG AT 16: Dexamethasone#
- Betamethasone (Clobetasol
- Clobetasone
- Diflorasone
- Halometasone
- Ulobetasol)
- Beclometasone
- Paramethasone
- Alclometasone
- Fluclorolone acetonide
- Flumetasone
- Fluprednidene
|
|
Pregnatriene
(+2-ene)
|
|
|
Androstene
|
- HALOGENATED, WITH FG AT 16: Fluticasone (Fluticasone propionate
- Fluticasone furoate)
|
|
Other/ungrouped
|
- HALOGENATED: Loteprednol
- HALOGENATED, WITH FG AT 16: Fludroxycortide
- Formocortal
- Mometasone furoate
|
|
|
Aldosterone antagonists |
- Spironolactone
- Eplerenone
- Potassium canrenoate
- Canrenone
|
|
Synthesis modifiers |
- Trilostane
- Carbenoxolone
- Aminoglutethimide
- Metyrapone
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
|
|
noco (d)/cong/tumr, sysi/epon
|
proc, drug (A10/H1/H2/H3/H5)
|
|
|
|
Glucocorticoids
|
|
Receptor |
|
|
Enzyme
(inhibitors) |
20,22-Desmolase
|
- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
|
|
17α-Hydroxylase,
17,20-Lyase
|
- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
|
|
3β-HSD
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Metyrapone
- Norethisterone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
|
|
21-Hydroxylase
|
- Aminoglutethimide
- Amphenone B
- Bifonazole
- Clotrimazole
- Diazepam
- Econazole
- Genistein
- Isoconazole
- Ketoconazole
- Metyrapone
- Miconazole
- Midazolam
- Tioconazole
|
|
11β-Hydroxylase
|
- Aminoglutethimide
- Canrenone
- Etomidate
- Fadrozole
- FETO
- Ketoconazole
- Metomidate
- Metyrapone
- Mitotane
- Potassium canrenoate
- Spironolactone
- Trilostane
|
|
18-Hydroxylase
|
- Aminoglutethimide
- Canrenone
- FAD286
- Fadrozole
- Ketoconazole
- LCI699
- Metyrapone
- Mespirenone
- Potassium canrenoate
- Spironolactone
|
|
|
Other |
Endogenous
|
- Glucocorticoids: Corticosterone
- Cortisone
- Cortodoxone/Deoxycortisol
- Hydrocortisone/Cortisol
- Antiglucocorticoids: 17-Hydroxyprogesterone
- Deoxycorticosterone
- Pregnenolone
- Progesterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- 17-Hydroxyprogesterone
- Progesterone
- Deoxycorticosterone
|
|
Indirect
|
- ACTH/Corticotropin
- CRH
- DHEA
- DHEA sulfate
- Plasma proteins (Transcortin, Albumin)
- Vasopressin
|
|
Procedures
|
- Adrenalectomy
- Hypophysectomy
|
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