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CORTISONE

CAS No.
53-06-5
Chemical Name:
CORTISONE
Synonyms
KE;Corlin;CORTONE;Cortison;17A 21-DIHYDROXY-4-PREGNEN-3 17 20-TRIONE;Corton;Adreson;Andreson;Cortisal;Cortogen
CBNumber:
CB6413305
Molecular Formula:
C21H28O5
Molecular Weight:
360.44
MDL Number:
MFCD00003610
MOL File:
53-06-5.mol
MSDS File:
SDS
Last updated:2023-09-25 13:50:22

CORTISONE 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)
Flash point 9℃
storage temp. -20°C Freezer
solubility Chloroform (Slightly, Heated, Sonicated), DMSO (Slightly), Ethanol (Slightly, Heated)
form Solid
pka 12.37±0.60(Predicted)
color White to Pale Beige
Water Solubility 229.9mg/L(25 ºC)
Merck 2539
LogP 1.470
CAS DataBase Reference 53-06-5(CAS DataBase Reference)
EWG's Food Scores 1
NCI Dictionary of Cancer Terms cortisone
FDA UNII V27W9254FZ
ATC code H02AB10,S01BA03

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS02,GHS06,GHS08
Signal word  Danger
Hazard statements  H225-H301+H311+H331-H370
Precautionary statements  P210-P260-P280-P301+P310-P311
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

CORTISONE price More Price(27)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C-130 Cortisone solution 100?μg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? 53-06-5 1ML $70.7 2024-03-01 Buy
Alfa Aesar J64182 Cortisone 53-06-5 1g $57.3 2024-03-01 Buy
Alfa Aesar J64182 Cortisone 53-06-5 5g $195 2024-03-01 Buy
TRC C696500 Cortisone 53-06-5 2g $100 2021-12-16 Buy
TRC C696500 Cortisone 53-06-5 5g $140 2021-12-16 Buy
Product number Packaging Price Buy
C-130 1ML $70.7 Buy
J64182 1g $57.3 Buy
J64182 5g $195 Buy
C696500 2g $100 Buy
C696500 5g $140 Buy

CORTISONE Chemical Properties,Uses,Production

Chemical Properties

Off-White Crystalline Powder

Originator

Cortone Acetate,MSD,US,1950

Uses

Cortisone is used for inflammatory processes, allergies, and adrenal insufficiency.

Uses

Anticoagulant

Uses

antiinflammatory, glucocorticoid

Uses

Glucocorticoid, anti-inflammatory agent

Definition

ChEBI: 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 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 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 Function

Glucocorticoid

General Description

Cortisone is a corticosteroid produced in the adrenal glands. Cortisone is administered for short term pain relief and to reduce swelling from inflammation. This Certified Spiking Solution? is applicable in LC-MS/MS applications for endocrinology, clinical chemistry and neonatal screening.

Hazard

Damaging side effects, e.g., sodium retention from ingestion.

Pharmacokinetics

Following 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 Use

Cortisone 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.

Synthesis

Cortisone, 17|á,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 11|á-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 |á-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).

Synthesis_53-06-5

Metabolism

The 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 Methods

Crystallise 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.]

53-03-2
53-06-5
Synthesis of CORTISONE from Prednisone
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Hubei Chuyan Biopharmaceutical Co., Ltd
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View Lastest Price from CORTISONE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
CORTISONE pictures 2024-03-13 CORTISONE
53-06-5
US $30.00 / kg 1kg 99.99% 20tons Hubei Chuyan Biopharmaceutical Co., Ltd
CORTISONE pictures 2022-07-16 CORTISONE
53-06-5
US $200.00 / g 10g 99% 25kg/ month Wuhan Qiami Technology Co., Ltd
Andreson pictures 2021-07-02 Andreson
53-06-5
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
  • CORTISONE pictures
  • CORTISONE
    53-06-5
  • US $30.00 / kg
  • 99.99%
  • Hubei Chuyan Biopharmaceutical Co., Ltd
  • CORTISONE pictures
  • CORTISONE
    53-06-5
  • US $200.00 / g
  • 99%
  • Wuhan Qiami Technology Co., Ltd
  • Andreson pictures
  • Andreson
    53-06-5
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd
17ALPHA,21-DIHYDROXYPREGN-4-ENE-3,11,20-TRIONE 17ALPHA,21-DIHYDROXY-4-PREGNENE-3,11,20-TRIONE 17ALPHA-HYDROXY-11-DEHYDROCORTICOSTERONE 17-HYDROXY-11-DEHYDROCORTICOSTERONE 4-PREGNENE-17ALPHA,21-DIOL-3,11,20-TRIONE 4-PREGNEN-17ALPHA,21-DIOL-3,11,20-TRIONE 4-PREGNEN-17,21-DIOL-3,11,20-TRIONE 4-PREGEN-17A,21-DIOL-3,11,20-TRIONE KENDALL'S CMPD ''E'' KENDALL'S ''E'' 4-Pregnene-17α,21-diol-3,11,20-trione (8S,9S,10R,13S,14S,17R)-17-glycoloyl-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-quinone (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyethanoyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxy-1-oxoethyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyethanoyl)-10,13-dimethyl-1,2,6,7,8,9,12 Cortisone solution,100ppm KENDALL'S COMPOUND E KENDALL'S COMPOUND 'E' CORTISONE DELTA4-PREGNENE-17, 21-DIOL-3, 11, 20-TRIONE DELTA4-PREGNENE-17ALPHA,21-DIOL-3,11,20-TRIONE DELTA-PREGNENE-17ALPHA,21-DIOL-3,11,20-TRIONE REICHSTEIN'S SUBSTANCE FA REICHSTEIN'S SUBSTANCE 'FA' REICHSTEIN'S COMPOUND ''FA'' WINTERSTEINER'S COMPOUND 'F' WINTERSTEINER'S CMPD ''F'' Corton (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione 17α,21-Dihydroxy-4-pregnene-3,11,20-trione, 17α-Hydroxy-11-dehydrocorticosterone, 4-Pregnene-17α,21-diol-3,11,20-trione, Kendalls Compound E, Reichsteins Substance Fa 17α,21-Dihydroxypregn-4-en-3,11,20-trione 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 Cortadren Cortandren Cortisal Cortisate Cortistal Cortivite Cortogen delta(sup4)-pregnene-17alpha,21-diol-3,11,20-trione Incortin Kendall's compound Pregn-4-en-17alpha,21-diol-3,11,20-trione Pregn-4-ene-3,11,20-trione, 17,21-dihydroxy- Reichstein Fa Scheroson (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-diMethyl-7,8,9,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11(2H,6H)-dione Cortisone solution Cortisone-[2H7] NSC 9703 4-Pregnen-17a,21-diol-3,11,20-trione-d2 11-DEHYDRO-17-HYDROXYCORTICOSTERONE 4-Pregnen-17α?21-diol-3?11?20-trione-1?2-d2