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F0891

Flumethasone pivalate

Name: Flumethasone pivalate
Brand: SIGMA

Synonym(s):

6α,9-Difluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-(2,2-dimethylpropionate), Flumetasone 21-pivalate, NSC 107680

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₃₆F₂O₆

CAS Number:

2002-29-1

Molecular Weight:

494.57

NACRES:

NA.85

PubChem Substance ID:

24894735

UNSPSC Code:

51101500

EC Number:

217-901-1

MDL number:

MFCD00079287

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Properties

form

solid

optical activity

[α]25/D 71.0 to 82.0°, c = 1 in dioxane

solubility

dioxane: 4.0 mL, clear, colorless to very faintly yellow (50 mg + 4.0 mL dioxane)

mode of action

cell membrane | interferes

SMILES string

[H][C@@]12C[C@@H](C)[C@](O)(C(=O)COC(=O)C(C)(C)C)[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/C27H36F2O6/c1-14-9-16-17-11-19(28)18-10-15(30)7-8-24(18,5)26(17,29)20(31)12-25(16,6)27(14,34)21(32)13-35-22(33)23(2,3)4/h7-8,10,14,16-17,19-20,31,34H,9,11-13H2,1-6H3/t14-,16+,17+,19+,20+,24+,25+,26+,27+/m1/s1

InChI key

JWRMHDSINXPDHB-OJAGFMMFSA-N

Gene Information

human ... NR3C1(2908)

Description

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 used to study adrenocortical suppression, plasma transcortin binding, and cutaneous atrophy and telangiectasia.

Biochem/physiol Actions

Flumethasone pivalate is a glucocorticoid receptor agonist used in studies on plasma transcortin binding. It binds to the nucleus causing a variety of genetic activations and repressions. The anti-inflammatory action 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.

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pictograms

GHS08

signalword

Warning

hcodes

H351

pcodes

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Carc. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c