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CORTISONE

CORTISONE Suppliers list
Company Name: Guangzhou PI PI Biotech Inc
Tel: ; +8618371201331;+8618371201331
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Products Intro: Product Name:Hydrocortisone impurity B (EP)
CAS:53-06-5
Purity:90%+ Package:10mg, 25mg, 50mg, 100mg, Other scale please email Sales@pipitech.com Remarks:17,21-dihydroxypregn-4-ene-3,11,20-trione (cortisone)
Company Name: Henan Tianfu Chemical Co.,Ltd.
Tel: 0371-55170693
Email: info@tianfuchem.com
Products Intro: Product Name:CORTISONE
CAS:‘53-06-5
Purity:0.99 Package:25KG,5KG;1KG;500G
Company Name: Hangzhou FandaChem Co.,Ltd.
Tel: 008615858145714
Email: fandachem@gmail.com
Products Intro: Product Name:Cortisone
CAS:53-06-5
Purity:As coa Package:As request Remarks:53-06-5
Company Name: Hubei XinRunde Chemical Co., Ltd.
Tel: +8615102730682; +8618874586545
Email: bruce@xrdchem.cn
Products Intro: Product Name:Andreson
CAS:53-06-5
Purity:98% Package:1KG;100USD
Company Name: Hubei Jusheng Technology Co.,Ltd.
Tel: 86-18871470254
Email: linda@hubeijusheng.com
Products Intro: Product Name:cortisone
CAS:53-06-5
Purity:99% Package:5KG;1KG Remarks:C21H28O5

CORTISONE manufacturers

  • Andreson
  • $15.00-10.00 / KG
  • 2021-07-02
  • CAS:53-06-5
  • Min. Order: 1KG
  • Purity: 99%+ HPLC
  • Supply Ability: Monthly supply of 1 ton
  • CORTISONE USP/EP/BP
  • $1.10 / g
  • 2021-06-05
  • CAS:53-06-5
  • Min. Order: 1g
  • Purity: 99.9%
  • Supply Ability: 100 Tons Min
  • CORTISONE
  • $1.00 / KG
  • 2020-01-10
  • CAS:53-06-5
  • Min. Order: 1KG
  • Purity: 98% HPLC
  • Supply Ability: 10 tons/month
CORTISONE Basic information
Product Name:CORTISONE
Synonyms:17,21-Dihydroxy-4-pregnene-3,11,20-trione;17,21-Dihydroxypregn-4-ene-3,11,20-trione;20-trione,17,21-dihydroxy-pregn-4-ene-11;Adrenalex;Adreson;Andreson;Corlin;Cortadren
CAS:53-06-5
MF:C21H28O5
MW:360.44
EINECS:200-162-4
Product Categories:Biochemistry;Hydroxyketosteroids;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;Intracellular receptor;Inhibitors
Mol File:53-06-5.mol
CORTISONE Structure
CORTISONE Chemical Properties
Melting point 223-228 °C (dec.)(lit.)
alpha D25 +209° (c = 1.2 in 95% alcohol); 25546 +269° (c = 0.125 in benzene); 25546 +248° (c = 0.1 to 0.2 in alcohol)
Boiling point 412.46°C (rough estimate)
density 1.28±0.1 g/cm3 (20 ºC 760 Torr)
refractive index 210 ° (C=1, EtOH)
Fp 9℃
storage temp. -20°C Freezer
pka12.37±0.60(Predicted)
Water Solubility 229.9mg/L(25 ºC)
Merck 2539
CAS DataBase Reference53-06-5(CAS DataBase Reference)
Safety Information
Hazard Codes F,T,Xn
Risk Statements 11-23/24/25-39/23/24/25-63
Safety Statements 22-24/25-45-36/37-16-7
RIDADR UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 3
RTECS GM9020000
18
HS Code 2937210000
MSDS Information
ProviderLanguage
SigmaAldrich English
CORTISONE Usage And Synthesis
Chemical PropertiesOff-White Crystalline Powder
OriginatorCortone Acetate,MSD,US,1950
UsesCortisone is used for inflammatory processes, allergies, and adrenal insufficiency.
UsesGlucocorticoid, anti-inflammatory agent
Usesantiinflammatory, glucocorticoid
UsesAnticoagulant
DefinitionChEBI: A C21-steroid that is pregn-4-ene substituted by hydroxy groups at positions 17 and 21 and oxo group at positions 3, 11 and 20.
Manufacturing ProcessThe 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 potassium
cyanide. 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 FunctionGlucocorticoid
HazardDamaging side effects, e.g., sodium retention from ingestion.
PharmacokineticsFollowing oral administration, cortisone acetate and hydrocortisone acetate are completely and rapidly deacetylated by first-pass metabolism. Much of the oral cortisone, however, is inactivated by oxidative metabolism before it can be converted to hydrocortisone in the liver. The pharmacokinetics for hydrocortisone acetate is indistinguishable from that of orally administered hydrocortisone. Oral hydrocortisone is completely absorbed, with a bioavailability of greater than 95% and a half-life of 1 to 2 hours (23).
Clinical UseCortisone is administered orally or by intramuscular (IM) injection as its 21-acetate (cortisone acetate).Cortisone acetate or hydrocortisone usually is the corticosteroid of choice for replacement therapy in patients with adrenocortical insufficiency, because these drugs have both glucocorticoid and mineralocorticoid properties.
Chemical SynthesisCortisone, 17α,21-dihydroxypregn-4-en-3,11,20-trione (27.1.26), is also synthesized in various ways from compounds already having the steroid skeleton. One of them is very similar to a method of making hydrocortisone described above, in which it is synthesized from progesterone, which undergoes microbiological oxidation, forming 11α-hydroxyprogesterone (27.1.9). The hydroxyl group of the last is oxidized by chromium(VI) oxide in acetic acid, giving 11-ketoprogesterone (27.1.10). This is reacted with diethyloxalate in the presence of sodium ethoxide, forming the corresponding α-ketoester in the form of a sodium enolate 27.1.11, which undergoes bromination with two equivalents of bromine, giving a dibromoketone 27.1.12. The resulting dibromoketone undergoes a Favorskii rearrangement, but the product is not hydrolyzed, and the unsaturated acid is isolated in the form of a methyl ester 27.1.20. Reacting this with pyrrolidine gives a dienamine 27.1.21, which undergoes reduction by lithium aluminum hydride, which results in that, the keto-group on C11 transforms into a hydroxyl group, and the carbmethoxy group to a primary alcohol, forming the compound 27.1.22. Acidic hydrolysis of the product and subsequent acetylation gives an acetate 27.1.23, and the hydroxyl group at C11 in which it is oxidized with chromium(VI) oxide to a ketone, forming the compound 27.1.24. This undergoes a reaction with osmium tetroxide, and the resulting osmate is oxidized by magnesium dioxide in N-methylmorpholine, giving cortisone acetate 27.1.25. Hydrolysis of the acetyl group using sodium bicarbonate leads to the formation of cortisone (27.1.26).

MetabolismThe metabolism of hydrocortisone has been previously described. Cortisone acetate is slowly absorbed from IM injection sites over a period of 24 to 48 hours and is reserved for patients who are unable to take the drug orally. The acetate ester derivative demonstrates increased stability and has a longer duration of action when administered by IM injection. Thus, smaller doses can be used. Similarly, hydrocortisone may be dispensed as its 21-acetate (hydrocortisone acetate), which is superior to cortisone acetate when injected intra-articularly.
Purification MethodsCrystallise cortisone from 95% EtOH or acetone. The UV has 14,000 M-1cm -1 at 237nm (EtOH). [Beilstein 8 IV 3480, Hems J Pharm Pharmacol 5 409 1953, Beilstein 8 IV 3480.]
Tag:CORTISONE(53-06-5) Related Product Information
Hydrocortisone acetate Cortisone Reductase cortisone sulfate 9-ALPHA-FLUORO-2-ALPHA-METHYL-CORTISONE 4-PREGNEN-6-ALPHA, 17,21-TRIOL-3,11,20-TRIONE CORTISONE 21-SULFATE AMMONIUM CORTISONE MESYLATE 2ALPHA-METHYLCORTISONE 16ALPHA-METHYLCORTISONE 4-PREGNEN-6-BETA, 17,21-TRIOL-3,11,20-TRIONE CORTISONE 21-HEMISUCCINATE 4-Pregnene-17,21-diol-3,11,20-trione 21-sulphate,sodium salt CORTISONE GLUCURONIDE,CORTISONE-21BETA-GLUCURONIDE CORTISONE, [4-14C] CORTISONE, [1,2-3H] CORTISONE-21BETA-GLUCURONIDE SODIUM 4-PREGNEN-17,21-DIOL-3,11,20-TRIONE SULPHATE, TRIETHYL AMMONIUM SALT Cortisone, 21-acetate (8CI),CORTISONE-21-ACETATE, PH EUR,CORTISONE 21-ACETATE,CORTISONE ACETATE,CORTISONE ACETATE CRYSTALLINE