Prednisone CAS 53-03-2
Introduction：Basic information about Prednisone CAS 53-03-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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). |
| 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. |
| Major Application | clinical testing |
| InChIKey | XOFYZVNMUHMLCC-ZPOLXVRWSA-N |
| SMILES | O[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 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 |
| WGK Germany | WGK 2 |
| TSCA | TSCA listed |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Eye Irrit. 2 Flam. Liq. 2 |
| Hazardous Substances Data | 53-03-2(Hazardous Substances Data) |
| 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 cortisoneand has less of an effect on mineral volume. |
| Uses | Adrenocortical steroid. Glucocorticoid, antiinflammatory. |
| Uses | Downregulates TNF-α production and NF-κB expression |
| 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. |
| Indications | Prednisone 2.5 to 7.5 mg, administered at night or dexamethasone 0.25to 0.75 mg are useful in female patients, with severe acne unresponsiveto conventional therapy, who suffer from adrenal gland overproductionof androgens such as congenital adrenal hyperplasia. |
| 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 byintraperitoneal and subcutaneous routes.Moderately toxic by intramuscular route.Human systemic effects: sensory changeinvolving peripheral nerves, dermatitis.Experimental reproductive effects.Questionable carcinogen with experimentaltumorigenic 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 C1and C2. There are various ways of synthesizing it. In one of these, as is in the case whensynthesizing cortisone, it is synthesized from dihydrocortisone acetate. However, in thegiven example, this compound undergoes dibromination by molecular bromine, giving2,4-dibromo-derivative of dihydrocortisone 27.1.30. Dehydrobromination with3,5-lutidine, followed by subsequent hydrolysis of the acetyl group using potassium bicarbonategives the desired prednisone (27.1.31). Prednisone is also synthesized bymicrobiological 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 |
