F9428

Fluticasone propionate

Name: Fluticasone propionate
Brand: SIGMA

≥98% (HPLC), anti-inflammatory agent, powder

Synonym(s):

(6α,11β,16α,17α)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)androsta-1,4-diene-17-carbothioic acid S-(fluoromethyl) ester

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About This Item

Empirical Formula (Hill Notation):

C₂₅H₃₁F₃O₅S

CAS Number:

80474-14-2

Molecular Weight:

500.57

UNSPSC Code:

12352200

PubChem Substance ID:

329799785

NACRES:

NA.77

MDL number:

MFCD00866007

Product Name

Fluticasone propionate, ≥98% (HPLC), powder

SMILES string

CCC(=O)O[C@@]1([C@H](C)C[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@]12C)C(=O)SCF

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

InChI key

WMWTYOKRWGGJOA-CENSZEJFSA-N

assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: ≥10 mg/mL

originator

GlaxoSmithKline

Quality Level

100

Gene Information

human ... NR3C1(2908)

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Bioactive Small Molecules

Biochem/physiol Actions

Fluticasone propionate is a second generation glucocorticoid. Used as an anti-inflammatory agent for asthma. Shown to enhance eosinophil apoptosis in a concentration-dependent manner via the glucocorticoid receptor.

Features and Benefits

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This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

General description

Fluticasone blocks mast cells, eosinophils, lymphocytes, neutrophils and macrophages.

pictograms

GHS08

signalword

Warning

hcodes

H361f,H373

pcodes

P202 - P260 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Repr. 2 - STOT RE 2

target_organs

Endocrine system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000217417

0000207384

0000134002

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Small Animal Clinical Pharmacology (2008)

Randomized controlled trial comparing aerosolized swallowed fluticasone to esomeprazole for esophageal eosinophilia.

Fouad J Moawad et al.

The American journal of gastroenterology, 108(3), 366-372 (2013-02-13)

Patients with clinical symptoms of esophageal dysfunction and dense eosinophilic infiltration of the esophageal mucosa are suspected to have eosinophilic esophagitis (EoE). Topical steroids are often used as first-line therapy for EoE, although some patients respond clinically to proton pump

Severe asthma in humans and mouse model suggests a CXCL10 signature underlies corticosteroid-resistant Th1 bias.

Marc Gauthier et al.

JCI insight, 2(13) (2017-07-07)

We previously showed that Th1/type 1 inflammation marked by increased IFN-γ levels in the airways can be appreciated in 50% of patients with severe asthma, despite high dose corticosteroid (CS) treatment. We hypothesized that a downstream target of IFN-γ, CXCL10

Long-acting β2-agonists increase fluticasone propionate-induced mitogen-activated protein kinase phosphatase 1 (MKP-1) in airway smooth muscle cells.

Melanie Manetsch et al.

PloS one, 8(3), e59635-e59635 (2013-03-28)

Mitogen-activated protein kinase phosphatase 1 (MKP-1) represses MAPK-driven signalling and plays an important anti-inflammatory role in asthma and airway remodelling. Although MKP-1 is corticosteroid-responsive and increased by cAMP-mediated signalling, the upregulation of this critical anti-inflammatory protein by long-acting β2-agonists and

Inhaled corticosteroid dose response using domiciliary exhaled nitric oxide in persistent asthma: the FENOtype trial.

William J Anderson et al.

Chest, 142(6), 1553-1561 (2013-02-01)

International guidelines advocate a standard approach to asthma management for all, despite its heterogeneity. "Personalized" treatment of inflammatory asthma phenotypes confers superior benefits. We wished to evaluate dose response to inhaled corticosteroids (ICSs) in patients with asthma with an elevated

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