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F9507

Sigma-Aldrich

Flumethasone

Synonym(s):

6α,9α-Difluoro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione, 6α,9α-Difluoro-16α-methylprednisolone, 6α-Fluorodexamethasone

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About This Item

Empirical Formula (Hill Notation):
C22H28F2O5
CAS Number:
Molecular Weight:
410.45
EC Number:
MDL number:
UNSPSC Code:
51102829
PubChem Substance ID:
NACRES:
NA.85

form

powder

color

white to off-white

solubility

acetic acid: 10 mg/mL

Mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

[H][C@@]12C[C@@H](C)[C@](O)(C(=O)CO)[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

1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1

InChI key

WXURHACBFYSXBI-GQKYHHCASA-N

Application

Flumethasone pivalate is a topical difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. A prompt decrease in inflammation, exudation and itching is experienced after application. It is commonly used in veterinary practice and has been used in cortisol assays to study early porcine conceptus development.

Biochem/physiol Actions

Flumethasone is a glucocorticoid receptor agonist used in studies on plasma transcortin binding. It binds to the nucleus causing a variety of genetic activation and repressions. The anti-inflammatory actions of flumethasone is thought to involve lipocortins and phospholipase A2 inhibitory proteins, which results in the inhibition of arachidonic acid and the control of prostaglandin and leukotriene biosynthesis. Flumethasone suppresses the immune system due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding .

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Flexor carpi ulnaris tendonopathy in a Weimaraner.
S Y Kuan et al.
Australian veterinary journal, 85(10), 401-404 (2007-10-02)
J P Antignac et al.
Rapid communications in mass spectrometry : RCM, 14(1), 33-39 (2000-01-07)
A screening method based on liquid chromatography/electrospray tandem mass spectrometry was developed in order to control the illegal use of corticosteroids as growth promoters in cattle. The objective was the detection of low residue levels of corticosteroids or metabolites in
G Brambilla et al.
Journal of chromatography. B, Biomedical sciences and applications, 755(1-2), 265-278 (2001-06-08)
Corticosteroids can be illegally administered to cattle as growth promoting agents to improve meat production. We developed a liquid chromatography-atmospheric pressure ionization mass spectrometry-mass spectrometry (LC-MS-MS) method able to identify and quantify flumethasone, one of the most potent fluorinated synthetic
Gianluca Damonte et al.
Journal of pharmaceutical and biomedical analysis, 43(1), 376-380 (2006-08-05)
Dexamethasone is a synthetic glucocorticoid with potent anti-inflammatory properties. However, its administration causes significant side effects, specially in long-term therapy. A new approach for limiting adverse effects consists in the slow and constant deliver of this drug, using dexamethasone-21-phosphate-loaded erythrocytes
Olivia Van den hauwe et al.
Journal of AOAC International, 88(1), 87-94 (2005-03-12)
Within the framework of a European Union (EU) research project entitled "Food Safety Screening: Synthetic Glucocorticoids (QLK1-1999-00122)," an international interlaboratory ring test was organized to compare and evaluate different liquid chromatography/mass spectrometry (LC/MS) confirmatory methods that are applied in European

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