50-04-4 Usage
Description
Cortisone acetate is a synthetic glucocorticoid with anti-inflammatory properties. It decreases the size of Bacillus Calmette-Guérin (BCG) vaccine-induced dermal lesions and tuberculin reactions in rabbits when administered at 2 mg/kg on alternate days over the course of 46 days. It also reduces the number and percentage of activated lesion-infiltrating mononuclear cells and decreases the amount of caseous necrosis and ulceration. Cortisone acetate (2.5 mg/kg per day, s.c.) slows tissue regeneration in a rabbit model of wound healing. It also decreases the number of dexamethasone binding sites on isolated human lymphocytes by 30%. Formulations containing cortisone acetate have been used to relieve inflammation, pruritic manifestations of corticosteroid-responsive dermatoses, and in the treatment of immune and allergic disorders.
Chemical Properties
solid
Originator
Cortone Acetate,MSD,US,1950
Uses
Different sources of media describe the Uses of 50-04-4 differently. You can refer to the following data:
1. Cortisone Acetate (Hydrocortisone Acetate EP Impurity D) is a glucocorticoid. Cortisone Acetate is an antiinflammatory agent. Cortisone Acetate is bioavailable and readily converted to the therapeutically active form, Hydrocotisone (H714615).
2. Cortisone Acetate is a glucocorticoid. Cortisone Acetate is an antiinflammatory agent. Cortisone Acetate is bioavailable and readily converted to the therapeutically active form, Hydrocotisone (H71461
5).
Manufacturing Process
The following technique is described in US Patent 2,541,104. A solution of 2.0
g of 3(α)-hydroxy-21-acetoxy-11,20-diketo-pregnane, which can be prepared
as described in Helv. Chim. Acta 27, 1287 (1944), is treated in a mixture of
25 cc of alcohol and 6.4 cc of acetic acid at 0°C with 6.0 g of potassiumcyanide. The solution is allowed to warm to room temperature and after 3
hours is diluted with water. The addition of a large volume of water to the
alcohol-hydrogen cyanide mixture precipitates a gum which is extracted with
chloroform or ethyl acetate. The extract is washed with water, and evaporated
to small volume under reduced pressure. The crystalline precipitate (1.3 g)
consists of 3(α),20-dihydroxy-20-cyano-21-acetoxy-11-keto-pregnane; dec.
175° to 185°C.A solution of 0.60 g of chromic acid in 1.2 cc of water and 11 cc of acetic acid
is added to a solution containing about 1.2 g of 3(α),20-dihydroxy-20-cyano-
21-acetoxy-11-ketopregnane at room temperature. After 1 hour, water is
added and the product, which precipitates, is filtered and recrystallized from
ethyl acetate to produce 3,11-diketo-20-hydroxy-20-cyano-21-acetoxypregnane; dec. 214° to 217°C.
0.40 cc of phosphorus oxychloride is added to a solution containing about 950
mg of 3,11-diketo-20-hydroxy-20-cyano-21-acetoxy-pregnane dissolved in 3
cc of pyridine. After standing at room temperature for 24 hours, the solution
is poured into water and dilute hydrochloric acid, extracted with benzene and
concentrated to dryness. The crude product, after chromatography gives one
main constituent, namely δ17-3,11-diketo-20-cyano-21-acetoxy-pregnene; MP
189° to 190°C.
A solution of 1.0 g of δ17-3,11-diketo-20-cyano-21-acetoxy-pregnene in 10 cc
of benzene is treated with 1.0 g of osmium tetroxide and 0.43 g of pyridine.
After standing at room temperature for 18 hours, the resulting solution is
treated successively with 50 cc of alcohol, and with 50 cc of water containing
2.5 g of sodium sulfite. The mixture is stirred for 30 hours, filtered, and the
filtrate acidified with 0.5 cc of acetic acid and concentrated to small volume in
vacuo. The aqueous suspension is then extracted four times with chloroform,
the chloroform extracts are combined, washed with water and concentrated to
dryness in vacuo. Recrystallization of the residue from acetone gives 9°C. This
compound is then treated with acetic anhydride and pyridine for 15 minutes at
room temperature to produce 3,11,20-triketo-17(α)-hydroxy-21-acetoxypregnane or cortisone acetate.
Therapeutic Function
Glucocorticoid
General Description
Cortisone acetate, 21-(acetyloxy)-17-hydroxypregn-4-ene-3,11,20-trione, is the 21-acetate of naturally occurring cortisone with good systemicanti-inflammatory activity and low-to-moderate salt-retentionactivity after its in vivo conversion to hydrocortisoneacetate. This conversion is mediated by 11β-hydroxysteroiddehydrogenase. It is used for the entire spectrum of uses discussedpreviously under the heading, “Therapeutic Uses ofAdrenal Cortex Hormones”—collagen diseases, Addisondisease, severe shock, allergic conditions, chronic lymphocyticleukemia, and many other indications. Cortisone acetateis relatively ineffective topically, mainly because itmust be reduced in vivo to hydrocortisone. Its plasma halflifeis only about 30 minutes, compared with 90 minutes to3 hours for hydrocortisone.
Purification Methods
Crystallise -1cortisone-21-acetate from acetone or CHCl3. The UV has 15,800 M-1cm at 238nm in dioxane. [Sarett J Biol Chem 162 601 1946, Beilstein 8 III 4058, 5 IV 3481.]
Check Digit Verification of cas no
The CAS Registry Mumber 50-04-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 50-04:
(4*5)+(3*0)+(2*0)+(1*4)=24
24 % 10 = 4
So 50-04-4 is a valid CAS Registry Number.
InChI:InChI=1/C23H30O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h10,16-17,20,28H,4-9,11-12H2,1-3H3/t16-,17-,20+,21+,22+,23+/m1/s1
50-04-4Relevant articles and documents
Method for treating prednisone acetate mother liquor
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Paragraph 0034-0066, (2021/06/02)
The invention relates to the technical field of chemical pharmacy, in particular to a method for treating prednisone acetate mother liquor. The method comprises the following steps: (1) adding a solvent and alkali liquor into the prednisone acetate mother liquor to carry out hydrolysis reaction; (2) after the hydrolysis reaction is finished, adjusting the reaction liquid to be neutral, concentrating under reduced pressure until a large amount of crystals are separated out, and performing suction filtration to obtain a hydrolysate crude product; (3) adding the hydrolysate crude product into a solvent, and refining to obtain a hydrolyzed refined product; (4) adding the hydrolyzed refined substance and a catalyst into a solvent, and reacting with acetic anhydride to obtain a mixture of prednisone acetate and cortisone acetate; and (5) fermenting and dehydrogenating the mixture to obtain the prednisone acetate. According to the treatment method, the prednisone acetate in the prednisone acetate mother liquor can be recycled, particularly, the prednisone acetate in the mother liquor can be recycled, the treatment cost is saved, and the yield of the prednisone acetate is increased; The method can well remove the dehydrogenation RSA and RSA impurities, and is stable in processand simple to operate.
Preparation method of prednisone
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Paragraph 0012; 0029-0030; 0033-0034; 0037-0038, (2021/03/05)
The invention discloses a preparation method of prednisone, and belongs to the technical field of preparation and processing of medicines. According to the method, hydrocortisone acetate is used as aninitial raw material, and the prednisone is prepared through three steps of oxidation, biological fermentation dehydrogenation and hydrolysis. According to the preparation method of prednisone, the defects of a traditional process are overcome, the target product is high in purity, good in quality stability, high in yield, low in production cost and mild in reaction condition, a highly toxic cyanide reagent is prevented from being used, and the method is easy and convenient to operate, suitable for industrial production and wide in market prospect.
Preparation method of cortisone-21-acetate
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Paragraph 0038; 0039; 0044-0048; 0053-0057; 0062-0066; 0071, (2020/11/25)
The invention provides a preparation method of cortisone-21-acetate. The preparation method comprises: A) in a protective atmosphere, mixing a compound as shown in a formula I with anhydrous dimethylsulfoxide, a halogenating reagent and a first acid catalyst to carry out an addition-elimination reaction, so as to obtain a compound as shown in a formula III; B) adding the compound shown in the formula III into an organic solvent, and then adding a second acid catalyst and a reducing agent for a reduction reaction to obtain cortisone-21-acetate. The reaction formula is shown in the description.According to the preparation method, a Jones reagent does not need to be adopted, generation of a large amount of chromium-containing wastewater is avoided, the production period is shortened, the production cost is reduced, and clean production is achieved. The purity of the cortisone-21-acetate prepared by the method reaches 99.0% or above, the yield reaches 93% or above, and the preparation method is simple to operate, energy-saving, consumption-reducing, environment-friendly, and particularly suitable for industrial production.
