ChemicalBook > CAS DataBase List > CORTISONE

CORTISONE

Product Name
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
Formula Weight
360.44
MOL File
53-06-5.mol
More
Less

CORTISONE Property

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)
More
Less

Safety

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
F 
18
HS Code 
2937210000
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H370Causes damage to organs

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P311Call a POISON CENTER or doctor/physician.

More
Less

N-Bromosuccinimide Price

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

CORTISONE Chemical Properties,Usage,Production

Chemical Properties

Off-White Crystalline Powder

Originator

Cortone Acetate,MSD,US,1950

Uses

Glucocorticoid, anti-inflammatory agent

Uses

antiinflammatory, glucocorticoid

Uses

Anticoagulant

Uses

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

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).

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.]

CORTISONE Preparation Products And Raw materials

Raw materials

Hydrogen peroxide Chromium(VI) oxide 16-Dehydropregnenolone acetate 16a,17a-Epoxyprogesterone

Preparation Products

Cortisone acetate
More
Less

CORTISONE Suppliers

Canada 2 China 146 Europe 2 France 2 Germany 9 India 16 Japan 3 Poland 1 Switzerland 1 United Kingdom 11 United States 36 Global 229
HBCChem, Inc.
Tel
+1-510-219-6317
Fax
+1-650-486-1361
Email
sales@hbcchem.com
Country
United States
ProdList
10648
Advantage
60
Target molecule Corp.
Tel
857-239-0968
Fax
857-239-8801
Email
service1@targetmol.com
Country
United States
ProdList
2559
Advantage
60
Musechem
Tel
+1-800-259-7612
Fax
+1-800-259-7612
Email
info@musechem.com
Country
United States
ProdList
4660
Advantage
60
InvivoChem
Tel
+1-708-310-1919 +1-13798911105
Fax
708-557-7486
Email
sales@invivochem.cn
Country
United States
ProdList
6391
Advantage
58
Standardpharm Co. Ltd.
Tel
86-714-3992388
Email
overseasales1@yongstandards.com
Country
United States
ProdList
14332
Advantage
58
Cato Research Chemicals Inc.
Tel
020-81215950 4000-868-328
Email
customer@uwalab.com
Country
United States
ProdList
10404
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
United States Biological
Tel
--
Fax
--
Email
sales@advtechind.com
Country
United States
ProdList
6075
Advantage
58
CarboMer, Inc.
Tel
--
Fax
--
Email
sales@carbomer.com
Country
United States
ProdList
4026
Advantage
67
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6962
Advantage
56
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
Selleck Chemicals LLC
Tel
--
Fax
--
Email
sales@selleckchem.com
Country
United States
ProdList
1848
Advantage
58
VWR International, LLC.
Tel
--
Fax
--
Email
@sargentwelch.com
Country
United States
ProdList
6262
Advantage
58
IsoSciences
Tel
--
Fax
--
Email
info@isosciences.com
Country
United States
ProdList
379
Advantage
58
Camphor Technologies Inc.
Tel
--
Fax
--
Country
United States
ProdList
148
Advantage
58
Spectrum Chemical Mfg. Corp.
Tel
--
Fax
--
Email
marketing@spectrumchemical.com
Country
United States
ProdList
3113
Advantage
60
Oakwood Products, Inc.
Tel
--
Fax
--
Email
sales@oakwoodchemical.com
Country
United States
ProdList
6193
Advantage
74
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
Matrix Scientific
Tel
--
Fax
--
Email
sales@matrixscientific.com
Country
United States
ProdList
6632
Advantage
80
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
Fragmenta
Tel
--
Fax
--
Email
sales@fragmenta.com
Country
United States
ProdList
1068
Advantage
0
Medical Isotopes
Tel
--
Fax
--
Email
stohler@medicalisotopes.com
Country
United States
ProdList
6181
Advantage
68
Advance Scientific & Chemical
Tel
--
Fax
--
Email
sales@advance-scientific.com
Country
United States
ProdList
6419
Advantage
71
Pfaltz & Bauer, Inc.
Tel
--
Fax
--
Email
sales@pfaltzandbauer.com
Country
United States
ProdList
6828
Advantage
72
2A PharmaChem USA
Tel
--
Fax
--
Email
sales@2apharmachem.com
Country
United States
ProdList
6137
Advantage
39
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
AK Scientific, Inc.
Tel
--
Fax
--
Email
sales@aksci.com
Country
United States
ProdList
6347
Advantage
65
Sciencelab.com, Inc.
Tel
--
Fax
--
Email
accounting@sciencelab.com
Country
United States
ProdList
4159
Advantage
82
Lab Express
Tel
--
Fax
--
Email
sales@labexpress.com
Country
United States
ProdList
1577
Advantage
67
Steraloids Inc.
Tel
--
Fax
--
Email
sales@steraloids.com
Country
United States
ProdList
2357
Advantage
68
Spectrum Chemicals & Laboratory Products
Tel
--
Fax
--
Email
sales@spectrumchemical.com
Country
United States
ProdList
6699
Advantage
77
MP Biomedicals, Inc.
Tel
--
Fax
--
Country
United States
ProdList
6561
Advantage
81
ChromaDex
Tel
--
Fax
--
Email
sales@chromadex.com
Country
United States
ProdList
2501
Advantage
76
BOSCHE SCIENTIFIC, LLC
Tel
--
Fax
--
Email
Sales@BoscheSci.com
Country
United States
ProdList
6477
Advantage
55
Research Plus, Inc.
Tel
--
Fax
--
Email
respls@aol.com
Country
United States
ProdList
3674
Advantage
51
More
Less

View Lastest Price from CORTISONE manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
Andreson 53-06-5
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27
Career Henan Chemical Co
Product
CORTISONE 53-06-5
Price
US $1.00/KG
Min. Order
1KG
Purity
98% HPLC
Supply Ability
10 tons/month
Release date
2020-01-09
Hubei XinRunde Chemical Co., Ltd.
Product
Andreson 53-06-5
Price
US $100.00/KG
Min. Order
10G
Purity
98%
Supply Ability
10MT
Release date
2018-03-13

53-06-5, CORTISONERelated Search:

Hydrocortisone acetate Cortisone, 21-acetate (8CI),CORTISONE-21-ACETATE, PH EUR,CORTISONE 21-ACETATE,CORTISONE ACETATE,CORTISONE ACETATE CRYSTALLINE 4-PREGNEN-6-BETA, 17,21-TRIOL-3,11,20-TRIONE CORTEXOLONE Hydrocortisone-17-butyrate Prednisone Benazepril Prednisolone-21-acetate Prednisone 21-acetate 5-Bromo-2,3-difluorophenol Hydrocortisone 11-DEHYDROCORTICOSTERONE 11-KETOPROGESTERONE CORTISONE 21-HEMISUCCINATE 4-Pregnene-17,21-diol-3,11,20-trione 21-sulphate,sodium salt CORTISONE GLUCURONIDE,CORTISONE-21BETA-GLUCURONIDE CORTISONE MESYLATE 4-PREGNEN-6-ALPHA, 17,21-TRIOL-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
  • Corlin
  • Cortadren
  • Cortandren
  • Cortisal
  • Cortisate
  • Cortison
  • Cortistal
  • Cortivite
  • Cortogen
  • delta(sup4)-pregnene-17alpha,21-diol-3,11,20-trione
  • Incortin
  • KE
  • 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
  • 17A 21-DIHYDROXY-4-PREGNEN-3 17 20-TRIONE
  • 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
  • Hydrocortisone EP Impurity B
  • (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
  • Hydrocortisone impurity B (EP)
  • KENDALL'S COMPOUND E
  • KENDALL'S COMPOUND 'E'
  • CORTONE
  • 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''