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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;Bicortone;Colisone;Cortan | | 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 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). | | form | Solid | | pKa | 12.36±0.60(Predicted) | | 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) | | NIST Chemistry Reference | Prednisone(53-03-2) | | IARC | 3 (Vol. 26, Sup 7) 1987 | | EPA Substance Registry System | Prednisone (53-03-2) |
| | Prednisone Usage And Synthesis |
| Chemical Properties | White or almost white, crystalline powder. | | Uses | Adrenocortical steroid. Glucocorticoid, antiinflammatory. | | Uses | Downregulates TNF-α production and NF-κB expression | | 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. | | 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. | | 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. | | 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. 
| | 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.] |
| | Prednisone Preparation Products And Raw materials |
| Raw materials | Selenium dioxide-->Hydrocortisone-->Cortisone acetate | | Preparation Products | Deprodone propionate-->11-alpha,17-alpha,21-trihydroxypregn-4-ene-3,20-dione-->Pregna-1,4-diene-3,11,20-trione, 17-hydroxy--->17,20:20,21-Bis[Methylenebis(oxy)]-pregna-1,4-diene-3,11-dione-->CORTISONE |
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