382-67-2 Usage
Uses
Used in Pharmaceutical Industry:
Desoximetasone is used as a glucocorticoid anti-inflammatory agent for the treatment of various skin disorders, including skin allergies and psoriasis. It helps to reduce inflammation, itching, and redness associated with these conditions.
Used in Impurity Detection:
Desoximetasone is also found as an impurity in Dexamethasone (D298800), which is another corticosteroid used for its anti-inflammatory and immunosuppressive properties. The presence of Desoximetasone in Dexamethasone can be detected and monitored to ensure the quality and safety of the pharmaceutical product.
Brand Name:
The brand name for Desoximetasone is Topicort (Taro), which was previously known as Desoxymethasone.
Originator
Topicorte,Roussel,France,1968
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.
Therapeutic Function
Antiinflammatory
Check Digit Verification of cas no
The CAS Registry Mumber 382-67-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,8 and 2 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 382-67:
(5*3)+(4*8)+(3*2)+(2*6)+(1*7)=72
72 % 10 = 2
So 382-67-2 is a valid CAS Registry Number.
InChI:InChI=1/C22H29FO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h6-7,9,12,15-16,18-19,24,27H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,18?,19-,20+,21+,22+/m1/s1
382-67-2Relevant articles and documents
PROCESS FOR THE PREPARATION OF 17-DESOXY-CORTICOSTEROIDS
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Page/Page column 15-16, (2012/02/05)
The present invention provides an improved process for the preparation of 17-desoxy corticosteroid derivatives in a single chemical step by reacting the 17-hydroxy starting material with an excess of Trimethylsilyl Iodide. The present invention is specifically advantageous in preparing 17-desoxy corticosteroid derivatives having one or more halogen groups at positions 2, 6, 7 or 9 of the corticosteroid such as Clocortolone or Desoximetasone.
Process for the synthesis of the hydroxyacetyl side-chain of steroids of the pregnane type, novel 21-hydroxy-20-oxo-17α-pregnane compounds and pharmaceutical preparations containing them
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, (2008/06/13)
The present invention relates to a novel general process for synthesizing a α- or β-oriented hydroxyacetyl side chain of steroids of the pregnane type, which comprises treating a corresponding steroid carbaldehyde in succession with formaldehyde dimethylmercaptal-S-oxide in the form of an alkali metal salt thereof, and with a strongly acid hydrolysing agent.Preferred final products are compounds of the formula STR1 wherein n is 1 or 2, R 2 represents methyl or difluoromethyl, and R 1 represents hydroxymethyl, methoxymethyl, acetoxymethyl or hydrogen, and, if n is 2 and/or R 2 is difluoromethyl, R 1 also represents methyl. These compounds act as agonists or antagonists of natural steroid hormones. The antigestagenic 19,21-dihydroxy-17α-pregn-4-ene-3,20-dione and its 6,7-dehydro derivatives and diacetates are of particular interest.
Cytotoxic nucleoside-corticosteroid phosphodiesters
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, (2008/06/13)
Nucleotides of nucleosides or bases having known cytotoxic activity are reacted with steroids, preferably corticosteroids, to form corresponding cytotoxic nucleoside-corticosteroid phosphodiester analogues of the formula: STR1 wherein: steroid is the residue formed by removal of a hydroxyl hydrogen atom from a natural or synthetic adrenal corticosteroid containing the characteristic cyclopentanophenanthrene nucleus which is esterified to the phosphate moiety at the 21-position; sugar is a naturally occurring pentose or deoxypentose in the furanose form, preferably ribose, deoxyribose, lyxose, xylose or arabinose and especially ribose, deoxyribose or arabinose, which is esterified to the phosphate moiety at the 5'-position and covalently bonded to the heterocycle moiety at the 1'-position to form a nucleoside; and heterocycle is a purine, pyrimidine, hydrogenated pyrimidine, triazolopurine or similar nucleoside base. The conjugates exhibit an enhanced therapeutic index as compared to the parent nucleoside or base compounds, and are thus useful cytotoxic, antiviral and antineoplastic agents.
