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Prednisone

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Prednisone Basic information
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)
  • Flash point:>200℃
  • storage temp. Refrigerator
  • 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)
  • Water Solubility 115mg/L(25 ºC)
  • Merck 7722
  • BRN 2065301
  • 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
MSDS
Prednisone Usage And Synthesis
  • Chemical PropertiesWhite or almost white, crystalline powder.
  • UsesAdrenocortical steroid. Glucocorticoid, antiinflammatory.
  • UsesDownregulates TNF-α production and NF-κB expression
  • 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.
  • 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.
  • 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.
  • 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.
  • Chemical SynthesisPrednisone is 17α,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.

  • 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.]
Prednisone Preparation Products And Raw materials
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