Desoximetason

Bezeichnung:Desoximetason

CAS-Nr382-67-2

Englisch Name:Desoximetasone

CBNumberCB0346960

SummenformelC22H29FO4

Molgewicht376.46

MOL-Datei382-67-2.mol

Synonyma

Desoximetason

Desoximetason physikalisch-chemischer Eigenschaften

Schmelzpunkt	213-215°C
alpha	D +109° (chloroform)
Siedepunkt	532.3±50.0 °C(Predicted)
Dichte	376.46
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
pka	12.98±0.10(Predicted)
Aggregatzustand	Solid
Farbe	White to Off-White
InChIKey	VWVSBHGCDBMOOT-SDKBDWEQNA-N
SMILES	[C@@]12([H])CCC3=CC(=O)C=C[C@]3(C)[C@@]1(F)[C@@H](O)C[C@]1(C)[C@H]([C@H](C)C[C@@]21[H])C(=O)CO \|&1:0,10,12,14,17,19,20,23,r\|
CAS Datenbank	382-67-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/21/22-36/37/38-40-43
S-Sätze:	22-26-36
WGK Germany	3
RTECS-Nr.	TU3834000
HS Code	29147000

Gefahreninformationscode (GHS)

Desoximetasone Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R40:Verdacht auf krebserzeugende Wirkung.
R43:Sensibilisierung durch Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Desoximetasone is a glucocorticoid.1 In vivo, desoximetasone (0.001-0.1 mg) reverses increases in epidermal cell proliferation induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in SENCAR mice when administered topically. It also reduces TPA-induced expression of IL-6, COX-2, iNOS, and c-Jun mRNA levels in the skin of SENCAR mice, indicating anti-inflammatory action. Formulations containing desoximetasone have been used in the treatment of psoriasis and atopic dermatitis.WARNING This product is not for human or veterinary use.
Chemische Eigenschaften
Off-White Solid
Originator
Topicorte,Roussel,France,1968
Definition
ChEBI: Dexamethasone in which the hydroxy group at the 17alpha position is substituted by hydrogen. A synthetic corticosteroid with glucocorticoid activity, it is used as an anti-inflammatory and anti-pruritic in the treatment of various skin dis rders, including skin allergies and psoriasis.
Manufacturing Process
(a) Production of 16α-Methyl-4-Pregnene-11β,21-diol-3,20-Dione (= 16αMethylcorticosterone): A fermenter of stainless steel having a 50 liter capacity is charged with 30 liters of a nutrient solution containing:
sterilized for hour at 120°C and after cooling, inoculated with a spore suspension of Curvularia lunata which is obtained by rinsing a seven day corn culture (15 grams corn) with approximately 100 cc of physiological sodium chloride solution.
After two days of culturing at 25°C under stirring (220 revolutions per minute) and ventilating (1.65 m3/hr), 18 liters of the obtained culture are removed under sterile conditions and introduced into a fermenter of the same size charged with 28.2 liters of a nutrient solution containing:
After 24 hours cultivation under stirring and ventilation as described above, 7.5 grams of 16α-methyldesoxycorticosterone, obtained by saponification of the corresponding 21-acetate and melting at 102-104°C, in 200 cc of ethanol are added and fermented under the same conditions for 28 hours.
The course of the fermentation is tested by removal of samples, which are extracted with methyl isobutyl ketone. The extract is analyzed by paper chromatography in a system of dioxane + toluene/propylene glycol.
After the end of the fermentation (28 hours) the culture broth is filtered off by suction over a large suction filter. The mycel residue is washed with water several times. The filtrate is extracted three times, each time with 10 liters of methyl isobutyl ketone. The extract is concentrated under vacuum in a circulating evaporator and in a round flask carefully dried under vacuum. The residue is crystallized from acetone/isopropyl ether. The melting point is 157- 158°C (fermentation yield = 60%). The pure product yield obtained after a second crystallization and chromatography of the mother liquor on silica gel amounts to 53% of the theoretical.
(b) 16α-Methyl-9α-Fluoro-4-Pregnene-11β,21-Diol-3,20-Dione: 7.5 grams of 16α-methyl-9α-fluoro-4-pregnene-21-ol-3,20-dione-21-acetate, obtained from Step (a) by acetylating with acetic anhydride in pyridine followed by reaction with HF in pyridine at 0°C, are fermented for 36 hours with Curvularia lunata (Mutant NRRL 2380), whereby the 21-acetate group is simultaneously saponified, and then further worked up. The residue is extracted with MIBK, subjected to chromatography on silica gel and there is obtained from chloroform/ethyl acetate (2:1) an eluate containing the 11βhydroxy compound, which is further dehydrogenated as the crude product.
(c) 16α-Methyl-9α-Fluoro-1,4-Pregnadiene-11β,21-Diol-3,20-Dione: 16αmethyl-9α-fluoro-β4-pregnene-11β,21-diol-3,20-dione obtained as the crude product under Step (b) above, is fermented with Bacillus lentus for 30 hours and further worked up. The residue is extracted with methyl isobutyl ketone and there is obtained as the crude product 16α-methyl-9α-fluoro-1,4- pregnadiene-11β,21-diol-3,20-dione.
Trademarks
Topicort (Taro) [Name previously used: Desoxymethasone.].
Therapeutic Function
Antiinflammatory
Allgemeine Beschreibung
Desoximetasone, 9-fluoro-11β, 21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione, like clocortolone pivalate, lacks a C17α OH group inits structure.

Desoximetasone Upstream-Materialien And Downstream Produkte

Desoximetason Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

382-67-2, Desoximetasone Verwandte Suche:

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