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Cortisone acetate

Cortisone acetate Structure
CAS No.
50-04-4
Chemical Name:
Cortisone acetate
Synonyms
artriona;cortelan;cortisyl;ricortex;NSC 49420;cortistab;biocortacetate;cortoneacetate;irisoneacetate;cortogenacetate
CBNumber:
CB9277612
Molecular Formula:
C23H30O6
Molecular Weight:
402.48
MOL File:
50-04-4.mol
MSDS File:
SDS
Modify Date:
2024/7/2 8:55:41

Cortisone acetate Properties

Melting point 237-240 °C(lit.)
Boiling point 577.3±50.0 °C(Predicted)
alpha D25 +164° (c = 0.5 in acetone); D25 +208 to +217° (dioxane)
Density 1.26±0.1 g/cm3(Predicted)
refractive index 212 ° (C=1, MeOH)
storage temp. 2-8°C
solubility Practically insoluble in water, freely soluble in methylene chloride, soluble in dioxan, sparingly soluble in acetone, slightly soluble in ethanol (96 per cent) and in methanol.
form Solid
pka 12.32±0.60(Predicted)
color White to Off-White
Water Solubility 19mg/L(25 ºC)
Merck 14,2539
BRN 2067543
Stability Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference 50-04-4(CAS DataBase Reference)
EPA Substance Registry System Cortisone acetate (50-04-4)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS08
Signal word  Warning
Hazard statements  H373-H361
Precautionary statements  P260-P314-P501-P201-P202-P281-P308+P313-P405-P501
Safety Statements  22-36/37-24/25
WGK Germany  3
RTECS  GM9140000
HS Code  32041200
NFPA 704
0
3 0

Cortisone acetate price More Price(5)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) C3130 Cortisone 21-acetate ≥99% 50-04-4 1G ₹6386.75 2022-06-14 Buy
Sigma-Aldrich(India) C3130 Cortisone 21-acetate ≥99% 50-04-4 5G ₹24832.55 2022-06-14 Buy
Sigma-Aldrich(India) C3130 Cortisone 21-acetate ≥99% 50-04-4 10G ₹36880.78 2022-06-14 Buy
Sigma-Aldrich(India) PHR1923 Cortisone Acetate Pharmaceutical Secondary Standard; Certified Reference Material 50-04-4 300MG ₹20621.63 2022-06-14 Buy
Sigma-Aldrich(India) C3130 Cortisone 21-acetate ≥99% 50-04-4 25G ₹74270.33 2022-06-14 Buy
Product number Packaging Price Buy
C3130 1G ₹6386.75 Buy
C3130 5G ₹24832.55 Buy
C3130 10G ₹36880.78 Buy
PHR1923 300MG ₹20621.63 Buy
C3130 25G ₹74270.33 Buy

Cortisone acetate Chemical Properties,Uses,Production

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

White needle crystal or crystalline powder (acetone), odorless. Stable in the air. Mp239- 241°C, specific rotation [α]20D+164°(0.5%, acetone), [α]23D+169°(chloroform), [α]25D+208°-+217°(dioxane), The ethanol solution of this product has a maximum absorption at a wavelength of 240nm. Soluble in chloroform (1:4), soluble in acetone (1:75), slightly soluble in ethanol and ether, and hardly soluble in water. This product dissolves in sulfuric acid and turns yellow without fluorescence (different from hydrocortisone acetate).

Uses

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.

Preparation

Cortisone acetate is prepared from dehydropregnenolone by epoxidation, Wolff's oxidation, mycoxidation, chromic acid oxidation, hydrogen bromide ring-opening, Raney's nickel-catalyzed debromination, iodination, and acetyloxy substitution.

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.]

References

1. Cortisone acetate in skin disease; local effect in the skin from topical application and local injection. DOI:10.1001/ARCHDERM.1952.01530210056007
2. McCue, R.E., Dannenberg, A.M., Jr., Huguchi, S., et al. The effect of cortisone on the accumulation, activation, and necrosis of macrophages in tuberculous lesions. Inflammation 3(2), 159-176 (1978). DOI:10.1007/BF00910737
3. Joseph, J., and Tydd, M. The effects of cortisone acetate on tissue regeneration in the rabbit’s ear. J. Anat. 115(Pt. 3), 445-460 (1973).
4. Schlechte, J.A., Ginsberg, B.H., and Sherman, B.M. Regulation of the glucocorticoid receptor in human lymphocytes. J. Steroid Biochem. 16(1), 69-74 (1982). DOI:10.1016/0022-4731(82)90145-5
5. Sittig's Pharmaceutical Manufacturing Encyclopedia
6. Textbook of organic medicinal and pharmaceutical chemistry. DOI:10.1002/jps.3030451120
7. Purification of Laboratory Chemicals DOI:10.5860/choice.50-6768

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11,20-trione,17,21-dihydroxy-pregn-4-ene-21-acetate 11-dehydro-17-hydroxycorticosterone-21-acetate 11-dehydro-17-hydroxycorticosteroneacetate 17,21-dihydroxypregn-4-ene-3,11,20-trioneacetate 4-PREGNEN-17ALPHA,21-DIOL-3,11,20-TRIONE ACETATE 4-PREGNEN-17,21-DIOL-3,11,20-TRIONE 21-ACETATE 4-PREGNENE-17ALPHA,21-DIOL-3,11,20-TRIONE 21-ACETATE 17ALPHA,21-DIHYDROXY-4-PREGNENE-3,11,20-TRIONE 21-ACETATE 17,21-DIHYDROXYPREGN-4-ENE-3,11,20-TRIONE 21 ACETATE CORTISONE 21-ACETATE CORTISONE ACETATE DELTA4-PREGNEN-17ALPHA-21-DIOL-3, 11, 20-TRIONE-21-ACETATE ACETIC ACID 2-((8S,9S,10R,13S,14S,17R)-17-HYDROXY-10,13-DIMETHYL-3,11-DIOXO-2,3,6,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-17-YL)-2-OXO-ETHYL ESTER 21-acetoxypregnen-17a-ol-3,11,20-trione 21-Acetoxypregnen-17alpha-ol-3,11,20-trione Cortisoneacetate,99% Cortison Acetate CORTISONE ACETATE CRYSTALLINE CORTISONE-21-ACETATE, PH EUR KENDALL'S COMPOUND 'E' ACETATE Pregn-4-ene-3,11,20-trione, 21-(acetyloxy)-17-hydroxy- CORTISONEACETATE,MICRONIZED,USP CORTISONEACETATE,POWDER,USP 21-Acetoxy-17-hydroxypregn-4-ene-3,11,20-trione 21-Acetoxy-17α-hydroxy-3,11,20-triketopregnene-4 21-Acetoxy-17α-hydroxypregn-4-ene-3,11,20-trione 4-Pregnene-17a,21-diol-3,11,20-trione 21-acetate Cortisone, 21-acetate (8CI) Cortisyl Artriona NSC 49420 20-trione,21-(acetyloxy)-17-hydroxy-pregn-4-ene-11 21-(acetyloxy)-17-hydroxypregn-4-ene-3,11,20-trione 21-acetoxy-17,alpha-hydroxy-3,11,20-triketopregnene-4 21-acetoxy-17,alpha-hydroxypregn-4-ene-3,11,20-trione acetatecortisone artriona biocortacetate compoundeacetate cortelan cortisonemonoacetate cortistab cortisyl cortogenacetate cortoneacetate irisoneacetate ricortex Pregn-4-ene-3,11,20-trione, 17,21-dihydroxy-, 21-acetate (7CI) 17α,21-Dihydroxy-4-pregnene-3,11,20-trione 21-acetate, 21-Acetoxy-4-pregnen-17α-ol-3,11,20-trione, 4-Pregnene-17α,21-diol-3,11,20-trione 21-acetate 17α,21-Dihydroxy-4-pregnene-3,11,20-trione 21-acetate, 21-Acetoxy-4-pregnen-17α-ol-3,11,20-trione, 4-Pregnene-17α,21-diol-3,11,20-trione 21-acetate, Cortisoni acetas 17,21-dihydroxypregn-4-ene-3,11,20-trione acetat Cortisone Acetate (150 mg) Cortison phosphate Cortone 21-Acetate CORTISONE ACETATE ONISED 2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-diMethyl-3,11-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate IMp. A (EP): Hydrocortisone Acetate 17α,21-Dihydroxy-4-pregnene-3,11,20-trione 21-acetate 21-Acetoxy-4-pregnen-17α-ol-3,11,20-trione