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Merck
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F0891

Sigma-Aldrich

Flumethasone pivalate

Synonyme(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

Formule empirique (notation de Hill):
C27H36F2O6
Numéro CAS:
2002-29-1
Poids moléculaire :
494.57
Numéro CE :
217-901-1
Numéro MDL:
MFCD00079287
Code UNSPSC :
51101500
ID de substance PubChem :
24894735
Nomenclature NACRES :
NA.85

Forme

solid

Activité optique

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

Solubilité

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

Mode d’action

cell membrane | interferes

Chaîne SMILES 

[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

Clé InChI

JWRMHDSINXPDHB-OJAGFMMFSA-N

Informations sur le gène

human ... NR3C1(2908)

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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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Warning

Mentions de danger

H351

Classification des risques

Carc. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

[Double-blind comparison of a betamethasone dipropionate-iodochloroxyquinoline combination and a flumethasone pivalate-iodochloroxyquinoline combination in the therapy of steroid-sensitive dermatoses with superinfection].
M Mosca et al.
Giornale italiano di dermatologia e venereologia : organo ufficiale, Societa italiana di dermatologia e sifilografia, 121(1), XI-XIV (1986-01-01)
Contact allergy to EDTA in a topical corticosteroid preparation.
A C de Groot
Contact dermatitis, 15(4), 250-252 (1986-10-01)
V Wienert et al.
Archives of dermatological research, 271(1), 19-27 (1981-01-01)
Test results are reported of the effect of salicylic acid on the vasoconstrictive effect of flumethasone pivalate. In specific, the depigmentation of the skin (identical with increase in lightness of the skin) following topical application of flumethasone pivalate was investigated
F Scaglione et al.
Drugs under experimental and clinical research, 11(8), 523-526 (1985-01-01)
The combination flumethasone pivalate + iodochlorohydroxychinoline drops was used in 40 patients, 24 males and 16 females, mean age 42.6 years, suffering from infectious enanthema (35%), periodontitis (30%), aphthous stomatitis (25%) and abscess due to prosthesis (10%). After application of
M Shohat et al.
Clinical pediatrics, 25(4), 209-212 (1986-04-01)
Fifteen infants with seborrheic dermatitis were treated with topical glucocorticosteroids (flumethasone pivalate 0.02%). Early morning plasma cortisol levels were determined prior to treatment, during the 10-day treatment period, and 2 days after its termination. The mean plasma cortisol level prior
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