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Prednisone

CAS No.
53-03-2
Chemical Name:
Prednisone
Synonyms
Deltasone;MOPP;PREDNISON;Prednisone Micronised;Cortan;Orasone;Paracort;Bicortone;Servisone;Prednicen-M
CBNumber:
CB6716222
Molecular Formula:
C21H26O5
Molecular Weight:
358.43
MDL Number:
MFCD00003608
MOL File:
53-03-2.mol
MSDS File:
SDS
Last updated:2024-01-23 14:06:52

Prednisone Properties

Melting point 236-238 °C(lit.)
alpha 169 º (c=0.5, dioxane)
Boiling point 410.86°C (rough estimate)
Density 1.1121 (rough estimate)
refractive index 170 ° (C=0.5, Dioxane)
Flash point >200℃
storage temp. 2-8°C
solubility Practically insoluble in water, slightly soluble in ethanol (96 per cent) and in methylene chloride. It shows polymorphism (5.9).
pka 12.36±0.60(Predicted)
form Solid
color White to Off-White
Water Solubility 115mg/L(25 ºC)
Merck 7722
BRN 2065301
BCS Class 1?
Stability Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference 53-03-2(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII VB0R961HZT
NCI Dictionary of Cancer Terms MOPP; prednisone
NCI Drug Dictionary prednisone
Proposition 65 List MOPP (vincristine-prednisone-nitrogen mustard-procarbazine mixture)
ATC code A07EA03,H02AB07
IARC 3 (Vol. 26, Sup 7) 1987
NIST Chemistry Reference Prednisone(53-03-2)
EPA Substance Registry System Prednisone (53-03-2)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS08
Signal word  Warning
Hazard statements  H373
Precautionary statements  P260
Hazard Codes  Xn
Safety Statements  36/37/39-45-26-16

Prednisone price More Price(36)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich P6254 Prednisone ≥98% 53-03-2 1G $43 2023-06-20 Buy
Sigma-Aldrich P6254 Prednisone ≥98% 53-03-2 5G $157 2023-06-20 Buy
Sigma-Aldrich Y0001921 Prednisone for peak identification European Pharmacopoeia (EP) Reference Standard 53-03-2 Y0001921 $215 2023-06-20 Buy
Sigma-Aldrich P6254 Prednisone ≥98% 53-03-2 10G $279 2023-06-20 Buy
Sigma-Aldrich P6254 Prednisone ≥98% 53-03-2 25G $537 2023-06-20 Buy
Product number Packaging Price Buy
P6254 1G $43 Buy
P6254 5G $157 Buy
Y0001921 Y0001921 $215 Buy
P6254 10G $279 Buy
P6254 25G $537 Buy

Prednisone Chemical Properties,Uses,Production

Chemical Properties

White or almost white, crystalline powder.

Uses

Prednisone is used for the same indications as cortisone for inflammatory processes, allergies, and adrenal gland insufficiency; however, it is somewhat more active than cortisone and has less of an effect on mineral volume.

Uses

Downregulates TNF-α production and NF-κB expression

Uses

Adrenocortical steroid. Glucocorticoid, antiinflammatory.

Definition

ChEBI: A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead f the oxo group at position 11), which is the active drug and also a steroid.

Indications

Prednisone 2.5 to 7.5 mg, administered at night or dexamethasone 0.25 to 0.75 mg are useful in female patients, with severe acne unresponsive to conventional therapy, who suffer from adrenal gland overproduction of androgens such as congenital adrenal hyperplasia.

brand name

Cortan (Halsey); Delta-Dome (Bayer); Deltasone (Pharmacia & Upjohn); Liquid Pred (Muro); Meticorten (Schering); Orasone (Solvay Pharmaceuticals); Paracort (Parke-Davis).

General Description

Odorless white crystalline powder.

General Description

Prednisone, Δ1-cortisone, 17,21-dihydroxypregna-1,4-diene-3,11,20-trione, has systemic activityvery similar to that of prednisolone, and because of itslower salt-retention activity, it is often preferred over cortisoneor hydrocortisone. Prednisone must be reduced in vivoto prednisolone to provide the active GC.

Air & Water Reactions

Very slightly water soluble .

Hazard

Questionable carcinogen.

Safety Profile

Poison by intraperitoneal and subcutaneous routes. Moderately toxic by intramuscular route. Human systemic effects: sensory change involving peripheral nerves, dermatitis. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Has been implicated in aplastic anemia.

Synthesis

Prednisone is 17|á,21-dihydroxypregna-1,4-dien-3,11-20-trione (27.1.31). Prednisone differs from cortisone in the presence of an additional double bond between C1 and C2. There are various ways of synthesizing it. In one of these, as is in the case when synthesizing cortisone, it is synthesized from dihydrocortisone acetate. However, in the given example, this compound undergoes dibromination by molecular bromine, giving 2,4-dibromo-derivative of dihydrocortisone 27.1.30. Dehydrobromination with 3,5-lutidine, followed by subsequent hydrolysis of the acetyl group using potassium bicarbonate gives the desired prednisone (27.1.31). Prednisone is also synthesized by microbiological dehydrogenation of cortisone.

Synthesis_53-03-2

Purification Methods

Crystallise prednisone from acetone/hexane, then recrystallise it from Me2CO. The monoacetate crystallises from Me2CO/hexane with m 227-233o(dec), [] D +186o (c 1, dioxane), and the diacetate crystallises from 25Me2CO/hexane with m 219-221o(dec), [] D +125o (c 1, CHCl3). [Hertzog et al. Tetrahedron 18 581 1962, Beilstein 8 IV 3531.]

53-06-5
53-03-2
Synthesis of Prednisone from CORTISONE
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View Lastest Price from Prednisone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Prednisone pictures 2024-03-16 Prednisone
53-03-2
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Prednisone pictures 2024-01-23 Prednisone
53-03-2
US $45.00-35.00 / kg 1kg 99.8% 200tons/year Sigma Audley
Prednisone pictures 2023-09-14 Prednisone
53-03-2
US $0.00-0.00 / kg 1kg 99% 50tons Wuhan Han Sheng New Material Technology Co.,Ltd
  • Prednisone pictures
  • Prednisone
    53-03-2
  • US $0.00 / KG
  • 98%+
  • WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
  • Prednisone pictures
  • Prednisone
    53-03-2
  • US $45.00-35.00 / kg
  • 99.8%
  • Sigma Audley
  • Prednisone pictures
  • Prednisone
    53-03-2
  • US $0.00-0.00 / kg
  • 99%
  • Wuhan Han Sheng New Material Technology Co.,Ltd
1,2-Dehydrocortisone 1,4-pregnadiene-16-alpha,21-diol-3,11,20-trione 11,20-trione,17,21-dihydroxy-pregna-4-diene-3 11,20-trione,17,21-hydroxy-pregna-4-diene-3 Ancortone Colisone Cortancyl Cortidelt delta-E delta-sone Deltison Deltisone Deltra Di-Adreson Encorton Encortone Enkorton Hostacortin In-Sone Juvason Lisacort meburamide Metacortandracin Meticorten NCI-C04897 nci-co4897 NSC 10023 nsc10023 Precort Prednilonga Prednizon 1,4-PREGNADIENE-17ALPHA,21-DIOL-3,11,20-TRIONE (8S,9S,10R,13S,14S,17R)-17-HYDROXY-17-(2-HYDROXY-ACETYL)-10,13-DIMETHYL-7,8,9,10,12,13,14,15,16,17-DECAHYDRO-6H-CYCLOPENTA[A]PHENANTHRENE-3,11-DIONE PREDNISONE, PH EUR Prednisone,98% 1,4-Pregnadiene-17a,21-diol-3,11,20-trione 17,21-Dihydroxypregna-1,4-diene-3,11,20-trione 1,4-pregnadiene-17α,21-diol-3,11,20-trione PREDNISONE,ANHYDROUS,MICRONIZED,USP PREDNISONE,ANHYDROUS,POWDER,USP 1,4-Pregnadiene-17α,21-diol-3,11,20-trione, 1-Cortisone, 17α,21-Dihydroxy-1,4-pregnadiene-3,11,20-trione, Dehydrocortisone, Prednisonum 1,4-Pregnadiene-17α,21-diol-3,11,20-trione, 1-Cortisone, 17α,21-Dihydroxy-1,4-pregnadiene-3,11,20-trione, Dehydrocortisone Apo-Prednisone Ancotone 17α,21-Dihydroxy-1,4-pregnadiene-3,11,20-trione Cotone Dacortin Decortancyl Decortin Decortisyl Dekortin delta E. delta(1)-dehydrocortisone delta(Sup1)-Cortisone delta(Sup1)-Dehydrocortisone delta-1,4-pregnadiene-17alpha,21-diol-3-11,20-trione delta-1-dehydrocortisone delta1-Dehydrocortisone