Fluocinolonacetonid

Bezeichnung:Fluocinolonacetonid

CAS-Nr67-73-2

Englisch Name:fluocinolone16,17-acetonide

CBNumberCB6394372

SummenformelC24H30F2O6

Molgewicht452.49

MOL-Datei67-73-2.mol

Synonyma

Fluocinolonacetonid

Fluocinolonacetonid physikalisch-chemischer Eigenschaften

Schmelzpunkt	267-269 °C(lit.)
Siedepunkt	578.5±50.0 °C(Predicted)
alpha	D +95° (chloroform)
Dichte	1.1826 (estimate)
Brechungsindex	103 ° (C=1, MeOH)
storage temp.	Refrigerator
Löslichkeit	Practically insoluble in water, soluble in acetone and in ethanol
pka	12.78±0.70(Predicted)
Farbe	White to Off-White
Wasserlöslichkeit	Soluble in water (partly), DMSO, alcohol, chloroform and methanol.
Merck	14,4150
InChIKey	FEBLZLNTKCEFIT-VSXGLTOVSA-N
CAS Datenbank	67-73-2(CAS DataBase Reference)
EPA chemische Informationen	Fluocinolone acetonide (67-73-2)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-40-20/21/22
S-Sätze:	26-36-22
WGK Germany	3
RTECS-Nr.	TU3830000
HS Code	2937220000
Giftige Stoffe Daten	67-73-2(Hazardous Substances Data)
Toxizität	LD50 oral in rat: > 4gm/kg

Gefahreninformationscode (GHS)

fluocinolone16,17-acetonide Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R40:Verdacht auf krebserzeugende Wirkung.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S22:Staub nicht einatmen.
Chemische Eigenschaften
Crystalline Solid
Originator
Synalar,Syntex,US,1961
Verwenden
A synthetic glucocorticoid VEGF inhibitor; anti-inflammatory.
Verwenden
Fluocinolone acetonide is primarily used in dermatology to reduce skin inflammation and relieve itching. It acts as an inhibitor of tumor cells and it can regulate lipid metabolism by modulating gene expression. It can also inhibit the expression of VEGF (vascular endothelial growth factor) in the retinal pigment epithelial cell line due to its high glucocorticoid receptor affinity. Furthermore, it can inhibit TNF-α angiogenesis.
Verwenden
Fluocinolone acetonide (Derma-Smoothe/FS, Flurosyn, Capex, Synalar) is a synthetic fluorinated corticosteroid.
Indications
Fluocinolone acetonide (Derma-Smoothe/FS, Flurosyn, Capex, Synalar) is a synthetic fluorinated corticosteroid.
Definition
ChEBI: A fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatme t of various skin disorders.
Manufacturing Process
A mixture of 1.2 grams of 6α-fluoro-16α-hydroxy-hydrocortisone, 4 cc of acetic anhydride and 8 cc of pyridine was heated at 60°C for 2 hours and then kept at room temperature for 2 hours. Ice and water were added and the solid was collected, washed with water, dried and recrystallized from methylene chloride-methanol, thus giving 1.05 grams of the 16,21-diacetate of 6α-fluoro-16α-hydroxy-hydrocortisone (solvated) of MP 182° to 187°C;concentration of the mother liquors afforded an additional 130 mg of the same compound, MP 184° to 187°C. By recrystallization from the same solvents there was obtained the compound with a lower constant melting point of 175° to 177°C.
2.94 grams of the 16,21-diacetate of 6α-fluoro-16α-hydroxy-hydrocortisone was mixed with 60 cc of dimethylformamide, 3.6 cc of pyridine and 2.4 cc of methane-sulfonyl chloride was heated on the steam bath for 2 hours. The diacetate of 6α-fluoro-16α-hydroxy-hydrocortisone had been prepared as set forth above, and further dried by azeotropic distillation with benzene; the dimethylformamide had been previously distilled. After the 2 hours on the steam bath the mixture was cooled and poured into saturated aqueous sodium bicarbonate solution; the product was extracted with methylene chloride, the extract was washed with water, dried over anhydrous sodium sulfate and the solvent was evaporated.
The residue was chromatographed on 90 grams of silica gel eluting the product with methylene chloride-acetone (9:1) and then recrystallizing from methylene chloride-methanol. There was thus obtained 1.6 grams of the 16,21-diacetate of 6α-fluoro-δ4,9(11)-pregnadiene-16α,-17α,21-triol-3,20-dione with MP 110° to 114°C; the analytical sample melted at 115° to 117°C, [α]D+23.5° (chloroform), λ max. 234 to 236 nm, log ε 4.18.
A mixture of 1.38 grams of the above compound and 15 cc of dioxane was treated with 1.9 cc of a 0.5 N aqueous solution of perchloric acid and 600 mg of N-bromoacetamide, adding the latter in the dark, in three portions, in the course of half an hour and under continuous stirring, It was then stirred for a further 1% hours in the dark, then the excess of reagent was decomposed by the addition of aqueous sodium bisulfite solution and ice water was added; the product was extracted with methylene chloride, washed with water, dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure, thus giving a yellow oil consisting of the 16,21-diacetate of 6α- fluoro-9α-bromo-16α-hydroxy-hydrocortisone which was used for the next step without further purification.
The above crude bromohydrin was mixed with 2.5 grams of potassium acetate and 60 cc of acetone and refluxed for 6 hours, at the end of which the acetone was distilled, water was added to the residue and the product was extracted with methylene chloride. The extract was washed with water, dried over anhydrous sodium sulfate and the solvent was evaporated. Recrystallization of the residue from methanol furnished 800 mg of the 16,21- diacetate of 6α-fluoro-9β,11β-oxido-δ4-pregnene-16α,17α,21-triol-3,20-dione with MP 120° to 124°C; by chromatography of the mother liquors on silica gel there was obtained 180 milligrams more of the same compound with MP 117° to 119°C. The analytical sample was obtained by recrystallization from methanol; it showed MP 125° to 127°C.
To a solution of 1.6 grams of anhydrous hydrogen fluoride in 2.85 grams of tetrahydrofurane and 10 cc of methylene chloride cooled to -60°C was added a solution of 650 mg of the 16,21-diacetate of 6α-fluoro-9β,11β-oxido-δ4- pregnene-16α,17α,21-triol-3,20-dione in 20 cc of methylene chloride and the mixture was kept at -10°C for 72 hours. It was then poured into saturated aqueous sodium bicarbonate solution and the organic layer was separated, washed with water, dried over anhydrous sodium sulfate and evaporated. The residue was reacetylated by heating with 3 cc of acetic anhydride and 6 cc of pyridine for 1 hour on th
Trademarks
Fluonid (Allergan); Fluotrex (Savage); FS Shampoo (Galderma); Retisert (Bausch & Lomb); Synalar (Medicis).
Therapeutic Function
Glucocorticoid, Antiinflammatory
Allgemeine Beschreibung
Fluocinolone acetonide,6α,9-difluoro-11β,21-dihydroxy-16α,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione, also known as6α-fluorotriamcinolone acetonide, is the 21-acetate derivativeof fluocinolone acetonide and is about 5 times morepotent than fluocinolone acetonide in at least one topicalactivity assay.

fluocinolone16,17-acetonide Upstream-Materialien And Downstream Produkte

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