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SML0099

Sigma-Aldrich

Fluocinonide

≥98% (HPLC)

Synonyma:

(6α,11β,16α)-21-(acetyloxy)-6,9-difluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione, Lonide

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About This Item

Empirický vzorec (Hillův zápis):
C26H32F2O7
Číslo CAS:
356-12-7
Molekulová hmotnost:
494.52
EC Number:
206-597-6
MDL number:
MFCD00079302
UNSPSC Code:
51111800
PubChem Substance ID:
329825157
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +75 to +90°, c = 1 in dichloromethane

color

white to tan

solubility

DMSO: ≥19 mg/mL

storage temp.

2-8°C

SMILES string

CC(=O)OCC(=O)[C@@]12OC(C)(C)O[C@@H]1C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]23C

InChI

1S/C26H32F2O7/c1-13(29)33-12-20(32)26-21(34-22(2,3)35-26)10-15-16-9-18(27)17-8-14(30)6-7-23(17,4)25(16,28)19(31)11-24(15,26)5/h6-8,15-16,18-19,21,31H,9-12H2,1-5H3/t15-,16-,18-,19-,21+,23-,24-,25-,26+/m0/s1

InChI key

WJOHZNCJWYWUJD-IUGZLZTKSA-N

Gene Information

human ... NR3C1(2908)

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Biochem/physiol Actions

Flucinonide is a fluorinated glucocorticid that is used as a topical anti-inflammatory agent. Recently, flucinonide and other fluorinated glucocorticolids were identified as smoothend agonists. Flucinonide induces expression of Gli-reporter luciferase in Shh-LIGHT2 cells.
Fluocinonide has been used to study its effect on T-cell proliferation.
Fluocinonide is shown to be effective in the treatment of atopic dermatitis and oral lichen planus (OLP).

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H300,H361

Hazard Classifications

Acute Tox. 2 Oral - Repr. 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Małgorzata Radwan-Oczko
Advances in clinical and experimental medicine : official organ Wroclaw Medical University, 22(6), 893-898 (2014-01-17)
Oral lichen planus is a common, chronic mucosal disease associated with a cell-mediated immunological dysfunction. The clinical manifestation is different when various forms, white and red, are considered. Erosive, atrophic, ulcerative lesions require long-term treatment, because of inflammation and severe
Emily Hix et al.
Dermatology online journal, 19(10), 20029-20029 (2013-10-22)
Adherence in the treatment of chronic inflammatory skin diseases such as atopic dermatitis is poor. Methods to improve adherence have proven difficult. To determine whether a short course of treatment with a high-potency corticosteroid will improve adherence compared to longer
N Deslauriers et al.
FEMS immunology and medical microbiology, 11(1), 45-55 (1995-03-01)
Using an experimental model in the mouse we have shown that both local and central lines of defense, involving CD4+ T cells, participate in a dynamic interaction to maintain a long-term carrier state of Candida albicans in the oral cavity.
Rapid cutaneous dissemination of persistently agminated lymphomatoid papulosis in a 9-year-old boy.
Derek V Chan et al.
Archives of dermatology, 147(11), 1340-1342 (2011-11-23)
Matthew T Woods et al.
Journal of drugs in dermatology : JDD, 10(2), 171-176 (2011-02-02)
To determine the effect a novel formulation of fluocinonide cream on skin barrier function in subjects with atopic dermatitis. The authors performed an open-label, investigator-blinded, side-by-side, controlled trial examining skin barrier function before and after a two-week course of a
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