Diflorasondi(acetat)

Bezeichnung:Diflorasondi(acetat)

CAS-Nr33564-31-7

Englisch Name:Diflorasone diacetate

CBNumberCB5754117

SummenformelC26H32F2O7

Molgewicht494.52

MOL-Datei33564-31-7.mol

Synonyma

Diflorasondi(acetat)

Diflorasondi(acetat) physikalisch-chemischer Eigenschaften

Schmelzpunkt	221-223° (dec)
alpha	D +61° (chloroform)
Siedepunkt	235°C (rough estimate)
Dichte	1.2001 (estimate)
storage temp.	Refrigerator
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
pka	12.63±0.70(Predicted)
Aggregatzustand	Solid
Farbe	White to Off-White
Wasserlöslichkeit	6.5mg/L(22 ºC)
CAS Datenbank	33564-31-7(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/21/22-40
S-Sätze:	22-36
WGK Germany	3
RTECS-Nr.	TU3722000
HS Code	2937220000

Gefahreninformationscode (GHS)

Diflorasone diacetate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R40:Verdacht auf krebserzeugende Wirkung.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
White Solid
Originator
Florone,Upjohn,US,1978
Verwenden
Anti-inflammatory (topical)
Verwenden
An anti-inflammatory and anti-itching corticosteroid usually present in topical creams.
Definition
ChEBI: The 17,21-diacetate derivative of diflorasone. It is used topically for its anti-inflammatory and antipruritic properties in the treatment of various skin disorders.
Manufacturing Process
6α-Fluoro-9β-epoxy-17α,21-dihydroxy-16α-methyl-1,4-pregnadiene-3,20- dione-21-acetate:To a solution of 6.78 g of 6α-fluoro-9α-bromo-11β,17α,21- trihydroxy-16α-methyl-1,4-pregnadiene-3,20-dione-21-acetate in 175 ml of acetone was added 6.78 g of potassium acetate and the resulting suspension was heated under reflux for a period of 17 hours. The mixture was then concentrated to approximately 60 ml volume at reduced pressure on the steam bath, diluted with water and extracted with methylene chloride. The methylene chloride extracts were combined, washed with water, dried over anhydrous sodium sulfate and evaporated. The residue was redissolved in methylene chloride and chromatographed over 500 g of Florisil anhydrous magnesium silicate. The column was eluted with 1 liter portions of hexanes (Skellysolve B) containing increasing proportions of acetone. There was so eluted 6α-fluoro-9β,11β-epoxy-16α-methyl-17α,21-dihydroxy-1,4- pregnadiene-3,20-dione-21-acetate which was freed of solvent by evaporation of the eluates.
6α,9α-Difluoro-11β,17α,21-trihydroxy-16α-methyl-1,4-pregnadiene-3,20- dione-2-1-acetate: To approximately 1.3 g of hydrogen fluoride contained in a polyethylene bottle and maintained at -60C was added 2.3 ml of tetrahydrofuran and then a solution of 500 mg (0,0012 mol) of 6α-fluoro9β,11β-epoxy-16α-methyl-17α,21-dihydroxy-1,4-pregnadiene-3,20-dione-21- acetate in two ml of methylene chloride. The steroid solution was rinsed in with an additional 1 ml of methylene chloride. The light red colored solution was then kept at approximately -30°C for 1 hour and at -10°C for 2 hours. At the end of this period it was mixed cautiously with an excess of cold sodium bicarbonate solution and the organic material extracted with the aid of additional methylene chloride.
The combined extracts were washed with water, dried over anhydrous sodium sulfate and concentrated to approximately 35 ml. The solution was chromatographed over 130 g of Florisil anhydrous magnesium silicate. The column was developed with 260 ml portions of hexanes (Skellysolve B) containing increasing proportions of acetone. There was thus eluted 6α,9αdifluoro-11β,17α,21-trihydroxy-16α-methyl-1,4-pregnadiene-3,20-dione-21- acetate which was freed of solvent by evaporation of the eluate fractions.
6α,9α-Difluoro-11β,17α,21-trihydroxy-16α-methyl-1,4-pregnadiene-3,20- dione: 3.25 g of 6α,9α-difluoro-11β,17α,21-trihydroxy-16α-methyl-1,4- pregnadiene-3,20-dione-21-acetate was dissolved in 325 ml of methanol, previously purged of air-oxygen by passing nitrogen through it for 10 minutes and thereto was added a solution of 1.63 g of potassium bicarbonate in 30 ml of water, similarly purged of oxygen. The mixture was allowed to stand at room temperature for a period of 5 hours in a nitrogen atmosphere, thereupon neutralized with 2.14 ml of acetic acid in 40 ml of water. The mixture was concentrated to approximately one-third volume at reduced pressure on a 60°C water bath. Thereupon 250 ml of water was added and the mixture chilled. The crystalline product was collected on a filter, washed with water and dried to give 6α,9α-difluoro-11β,17α,21-trihydroxy-16αmethyl-1,4-pregnadiene-3,20-dione.
The diflorasone is reacted with orthoacetic acid trimethyl ester in the presence of toluenesulfonic acid to give diflorasone diacetate.
Trademarks
Florone (Pharmacia & Upjohn); Psorcon (Pharmacia & Upjohn); Psorcon (Sanofi Aventis).
Therapeutic Function
Antiinflammatory

Diflorasone diacetate Upstream-Materialien And Downstream Produkte

Diflorasondi(acetat) Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

33564-31-7, Diflorasone diacetate Verwandte Suche:

Send Inquriy