Prednisone 53-03-2 CAS NO.53-03-2

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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
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 Information

Hazard Codes	Xn
Safety Statements	36/37/39-45-26-16
Hazardous Substances Data	53-03-2(Hazardous Substances Data)

MSDS Information

Provider	Language
1,4-Pregnadiene-17a,21-diol-3,11,20-trione	English
SigmaAldrich	English

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.
Chemical Synthesis	Prednisone 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 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

 

 

 

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