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Safety Information

F0891

Sigma-Aldrich

Flumethasone pivalate

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
EC Number:
217-901-1
MDL number:
MFCD00079287
UNSPSC Code:
51101500
PubChem Substance ID:
24894735
NACRES:
NA.85

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)

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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.

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.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H351

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

Regulatory Information

监管及禁止进口产品

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Certificates of Analysis (COA)

Lot/Batch Number
048F0374
048F0374V

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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
[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)
[Release of flumethasone pivalate from oleogel and W/O emulsion bases in vitro].
W Horsch et al.
Die Pharmazie, 37(11), 807-808 (1982-11-01)
[Darkness effect in photochemotherapy. I. Effect of 8-methoxypsoralen on the epidermal patch test in allergic contact eczema].
H Meffert et al.
Dermatologische Monatschrift, 169(1), 46-48 (1983-01-01)
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