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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H31F3O5S
Molecular Weight 500.571
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUTICASONE PROPIONATE

SMILES

[H][C@@]12C[C@@H](C)[C@](OC(=O)CC)(C(=O)SCF)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])C[C@H](F)C4=CC(=O)C=C[C@]34C

InChI

InChIKey=WMWTYOKRWGGJOA-CENSZEJFSA-N
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

HIDE SMILES / InChI

Molecular Formula C25H31F3O5S
Molecular Weight 500.571
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 propionate, a medium-potency synthetic corticosteroid, is used topically to relieve inflammatory and pruritic symptoms of dermatoses and psoriasis, intranasally to manage symptoms of allergic and non-allergic rhinitis, and orally for the treatment of asthma. Fluticasone proprionate is marketed under several different brand names such as Flonase®. Fluticasone propionate is also available as a combination product of azelastine hydrochloride and fluticasone propionate called Dymista™. Dymista™ is indicated in patients over 12 years old for symptomatic relief of seasonal allergic rhinitis. Fluticasone propionate binds to the glucocorticoid receptor. Unbound corticosteroids cross the membranes of cells such as mast cells and eosinophils, binding with high affinity to glucocorticoid receptors (GR). The results include alteration of transcription and protein synthesis, a decreased release of leukocytic acid hydrolases, reduction in fibroblast proliferation, prevention of macrophage accumulation at inflamed sites, reduction of collagen deposition, interference with leukocyte adhesion to the capillary wall, reduction of capillary membrane permeability and subsequent edema, reduction of complement components, inhibition of histamine and kinin release, and interference with the formation of scar tissue. In the management of asthma, the glucocorticoid receptor complexes down-regulates proinflammatory mediators such as interleukin-(IL)-1, 3, and 5, and up-regulates anti-inflammatory mediators such as IkappaB [inhibitory molecule for nuclear factor kappaB1], IL-10, and IL-12. The antiinflammatory actions of corticosteroids are also thought to involve inhibition of cytosolic phospholipase A2 (through activation of lipocortin-1 (annexin)) which controls the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.0 nM [EC50]
0.7 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CUTIVATE

Cmax

ValueDoseCo-administeredAnalytePopulation
23364 pg/mL
1000 μg single, intravenous
FLUTICASONE PROPIONATE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
14148 pg × h/mL
1000 μg single, intravenous
FLUTICASONE PROPIONATE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4.1 h
1000 μg single, intravenous
FLUTICASONE PROPIONATE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
9%
1 mg single, intravenous
FLUTICASONE PROPIONATE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Dermatitis Cream/Ointment: Apply a thin film to affected area twice a day
Route of Administration: Topical
In Vitro Use Guide
Pretreatment with Fluticasone propionate (10(-11) M to about 10(-7) M, 24 h) inhibited TNF-alpha-induced VCAM-1 mRNA expression in BEAS-2B in a dose-dependent manner
Substance Class Chemical
Record UNII
O2GMZ0LF5W
Record Status Validated (UNII)
Record Version