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Prednisone

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Prednisone Basic information
Product Name:Prednisone
Synonyms: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
CAS:53-03-2
MF:C21H26O5
MW:358.43
EINECS:200-160-3
Product Categories:Antitumors for Research and Experimental Use;Biochemistry;Hydroxyketosteroids;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;Steroid and Hormone
Mol File:53-03-2.mol
Prednisone Structure
Prednisone Chemical 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)
Fp >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).
pKa12.36±0.60(Predicted)
form Solid
color White to Off-White
Water Solubility 115mg/L(25 ºC)
Merck 7722
BRN 2065301
BCS Class1?
Stability:Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference53-03-2(CAS DataBase Reference)
IARC3 (Vol. 26, Sup 7) 1987
NIST Chemistry ReferencePrednisone(53-03-2)
EPA Substance Registry SystemPrednisone (53-03-2)
Safety Information
Hazard Codes Xn
Safety Statements 36/37/39-45-26-16
Hazardous Substances Data53-03-2(Hazardous Substances Data)
MSDS Information
ProviderLanguage
1,4-Pregnadiene-17a,21-diol-3,11,20-trione English
SigmaAldrich English
Prednisone Usage And Synthesis
Chemical PropertiesWhite or almost white, crystalline powder.
UsesPrednisone 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.
UsesDownregulates TNF-α production and NF-κB expression
UsesAdrenocortical steroid. Glucocorticoid, antiinflammatory.
DefinitionChEBI: 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.
IndicationsPrednisone 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 nameCortan (Halsey); Delta-Dome (Bayer); Deltasone (Pharmacia & Upjohn); Liquid Pred (Muro); Meticorten (Schering); Orasone (Solvay Pharmaceuticals); Paracort (Parke-Davis).
General DescriptionOdorless white crystalline powder.
General DescriptionPrednisone, 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 ReactionsVery slightly water soluble .
HazardQuestionable carcinogen.
Safety ProfilePoison 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.
SynthesisPrednisone 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 MethodsCrystallise 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.]
Tag:Prednisone(53-03-2) Related Product Information
PREDNISONE SODIUM PHOSPHATE Hydrocortisone sodium succinate Fludrocortisone Hydrocortisone-17-butyrate CORTISONE Prednisolone Prednisolone sodium succinate Methylprednisolone Hydrocortisone prednisone 21-acetate,PREDNISONE ACETATE Dexamethasone-17-acetate 6alpha-Methylprednisolone sodium succinate Methylprednisolone acetate Prednisolone-21-acetate PREDNISONE HEMISUCCINATE:HISTAMINE chloroprednisone 21-acetate PREDNISONE 21-HEMISUCCINATE,PREDNISONE HEMISUCCINATE Pregna-1,4-diene-3,11,20-trione, 17-hydroxy-21-(phosphonooxy)-, disodium salt Prednisone Tablets