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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H27F3O4S
Molecular Weight 444.508
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUTICASONE

SMILES

C[C@@H]1C[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@]2(C)[C@@]1(O)C(=O)SCF

InChI

InChIKey=MGNNYOODZCAHBA-GQKYHHCASA-N
InChI=1S/C22H27F3O4S/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-19(15,2)21(14,25)17(27)9-20(13,3)22(11,29)18(28)30-10-23/h4-5,7,11,13-14,16-17,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H27F3O4S
Molecular Weight 444.508
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Fluticasone is a medium-potency synthetic trifluorinated corticosteroid which is used in some countries to manage nasal symptoms of allergic and non-allergic rhinitis. Fluticasone binds and activates glucocorticoid receptor, resulting in the activation of lipocortin. Lipocortin, in turn, inhibits cytosolic phospholipase A2, which triggers a cascade of reactions involved in the synthesis of inflammatory mediators, such as prostaglandins and leukotrienes. Both the furoate and propanoate esters, fluticasone furoate and fluticasone propionate, are much more commonly used as topical anti-inflammatories and inhaled corticosteroids.

Approval Year

Cmax

ValueDoseCo-administeredAnalytePopulation
0.09 ng/mL
0.25 mg single, respiratory
FLUTICASONE PROPIONATE serum
Homo sapiens
0.15 ng/mL
0.5 mg single, respiratory
FLUTICASONE PROPIONATE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
0.69 ng × h/mL
0.25 mg single, respiratory
FLUTICASONE PROPIONATE serum
Homo sapiens
1.47 ng × h/mL
0.5 mg single, respiratory
FLUTICASONE PROPIONATE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5.2 h
0.25 mg single, respiratory
FLUTICASONE PROPIONATE serum
Homo sapiens
5.9 h
0.5 mg single, respiratory
FLUTICASONE PROPIONATE serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.7%
unknown, unknown
FLUTICASONE PROPIONATE plasma
Homo sapiens

PubMed

Substance Class Chemical
Record UNII
CUT2W21N7U
Record Status Validated (UNII)
Record Version