Prednisone Property

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)

NIST Chemistry Reference

Prednisone(53-03-2)

IARC

3 (Vol. 26, Sup 7) 1987

EPA Substance Registry System

Prednisone (53-03-2)

Safety

Hazard Codes 

Xn

Safety Statements 

36/37/39-45-26-16

Hazardous Substances Data

53-03-2(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

Prednisone Chemical Properties,Usage,Production

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.]