Fluocinonide

Fluocinonide Basic information
Product Name:Fluocinonide
Synonyms:Cortalar;Gelisyn;Lidemol;Fluocinonide (100 mg);Fluocinonide(Vanos);(6α,11β,16α)-21-(Acetyloxy)-6,9-difluoro-11-hydroxy-16,17-[(1-Methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione;Flucetonide;Vanos
CAS:356-12-7
MF:C26H32F2O7
MW:494.52
EINECS:206-597-6
Product Categories:Steroids;LIDEX;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors;API;356-12-7
Mol File:356-12-7.mol
Fluocinonide Structure
Fluocinonide Chemical Properties
Melting point 309 °C
alpha D +83° (chloroform)
Boiling point 235°C (rough estimate)
density 1.2001 (estimate)
storage temp. 2-8°C
solubility DMSO: ≥19mg/mL
pka12.77±0.70(Predicted)
form powder
color white to tan
optical activity[α]/D +75 to +90°, c = 1 in dichloromethane
Water Solubility 0.53mg/L(25 ºC)
InChIKeyWJOHZNCJWYWUJD-IUGZLZTKSA-N
Safety Information
Hazard Codes T+
Risk Statements 28-63
Safety Statements 22-25-28-36/37/39-45
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS TU3831000
HazardClass 6.1(a)
PackingGroup I
HS Code 2937220000
Toxicityguinea pig,LD50,subcutaneous,> 3170mg/kg (3170mg/kg),Drugs in Japan Vol. 6, Pg. 694, 1982.
MSDS Information
ProviderLanguage
SigmaAldrich English
Fluocinonide Usage And Synthesis
Chemical PropertiesWhite Solid
OriginatorTopsyn ,Recordati,Italy,1970
UsesGlucocorticoid; anti-inflammatory.
UsesFluocinonide (Lidex, Lidex E, Fluonex) is a synthetic fluorinated corticosteroid.
IndicationsFluocinonide (Lidex, Lidex E, Fluonex) is a synthetic fluorinated corticosteroid.
DefinitionChEBI: Fluocinonide is an organic molecular entity.
Manufacturing ProcessTo a suspension of 500 mg of 6α-fluoro-triamcinolone in 75 ml of acetone is added 0.05 milliliters of 72% perchloric acid and the mixture agitated-at room temperature for 3 hours. During this period the crystals gradually dissolve and the clear solution is neutralized with dilute bicarbonate and the acetone removed in vacuo. The resulting crystalline suspension is filtered and the crystals washed with water. The dried material is recrystallized from 95% alcohol to give the pure acetonide.
A solution of 50 mg of 6α-fluoro-triamcinolone acetonide in 1 ml of pyridine and 1 ml of acetic anhydride is allowed to stand at room temperature for 18 hours. Removal of the reagents in vacuo gives a crystalline residue which after crystallization from acetone-hexane gives the pure 16α,17α- isopropylidene 6α-fluoro-triamcinolone 21 acetate (fluocinonide), as described in US Patent 3,197,469.
Brand nameLidex (Medicis); Vanos (Medicis).
Therapeutic FunctionAntiinflammatory, Glucocorticoid
Biochem/physiol ActionsFlucinonide 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.
Triamcinolone acetonide Fluocinonide CP2000 (S)-Glyceraldehyde acetonide ACETONE DI-N-BUTYL ACETAL Triamcinolone (1-FLUOROCYCLOHEXYL)METHANOL Descinolone 2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde DIPENTOXYETHANE 2-FLUORO-2-METHYL-PROPAN-1-OL ACETALDEHYDE DI-N-HEXYL ACETAL Fluocinonide 3-METHOXY-3-METHYLBUTYL ACETATE 2,2-Dimethyl-4-hexyl-1,3-dioxolane 1,3-DIMETHOXYACETONE 6alpha,9-difluoro-11beta-hydroxy-16alpha,17-[isopropylidenebis(oxy)]pregna-1,4-diene-3,20-dione 21-propionate L-(+)-Erythrulose 6-alpha-Fluoro-isoflupredone

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