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Prednisone

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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 Structure
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).
pKa12.36±0.60(Predicted)
form Solid
color White to Off-White
Water Solubility 115mg/L(25 ºC)
Merck 7722
BRN 2065301
BCS Class1?
Stability:Stable. Incompatible with strong oxidizing agents.
Major Applicationclinical testing
InChIKeyXOFYZVNMUHMLCC-ZPOLXVRWSA-N
SMILESO[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)C=C4)CC3)C)C(=O)C2)CC1)C)C(=O)CO
CAS DataBase Reference53-03-2(CAS DataBase Reference)
NIST Chemistry ReferencePrednisone(53-03-2)
IARC3 (Vol. 26, Sup 7) 1987
EPA Substance Registry SystemPrednisone (53-03-2)
Safety Information
Hazard Codes Xn
Safety Statements 36/37/39-45-26-16
WGK Germany WGK 2
TSCA TSCA listed
Storage Class3 - Flammable liquids
Hazard ClassificationsAcute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Flam. Liq. 2
Hazardous Substances Data53-03-2(Hazardous Substances Data)
MSDS Information
ProviderLanguage
1,4-Pregnadiene-17a,21-diol-3,11,20-trione English
SigmaAldrich English
Prednisone Usage And Synthesis
Chemical PropertiesWhite or almost white, crystalline powder.
HistoryThe 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.
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.
UsesAdrenocortical steroid. Glucocorticoid, antiinflammatory.
UsesDownregulates TNF-α production and NF-κB expression
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.
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.
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.
SynthesisPrednisone 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.

Synthesis_53-03-2

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.]
Tag:Prednisone(53-03-2) Related Product Information
Hydrocortisone-17-butyrate CORTISONE Prednisolone Fludrocortisone PREDNISONE SODIUM PHOSPHATE Hydrocortisone sodium succinate Prednisolone sodium succinate prednisone 21-acetate,PREDNISONE ACETATE Hydrocortisone Dexamethasone-17-acetate Methylprednisolone sodium succinate Methylprednisolone acetate Prednisolone-21-acetate Methylprednisolone PREDNISONE HEMISUCCINATE:HISTAMINE chloroprednisone 21-acetate PREDNISONE 21-HEMISUCCINATE,PREDNISONE HEMISUCCINATE Pregna-1,4-diene-3,11,20-trione, 17-hydroxy-21-(phosphonooxy)-, disodium salt Prednisone Tablets

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