Chemical Properties
White or almost white, crystalline powder.
History
The first isolation and structure identifications of prednisone and prednisolone were done in 1950 by Arthur Nobile. The first commercially feasible synthesis of prednisone was carried out in 1955 in the laboratories of Schering Corporation, which later became Schering-Plough Corporation, by Arthur Nobile and coworkers. They discovered that cortisone could be microbiologically oxidized to prednisone by the bacterium Corynebacterium simplex. Prednisone was introduced in 1955 by Schering, under the brand name Meticorten.
Prednisone was patented in 1954 and approved for medical use in the United States in 1955. In 2023, it was the 38th most commonly prescribed medication in the United States, with more than 15 million prescriptions.
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.
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, Δ
1-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.]
