| Name | Cortisone |
|---|---|
| Synonyms | 11-DEHYDRO-17-HYDROXYCORTICOSTERONE 17A 21-DIHYDROXY-4-PREGNEN-3 17 20-TRIONE 17ALPHA,21-DIHYDROXY-4-PREGNENE-3,11,20-TRIONE 17ALPHA,21-DIHYDROXYPREGN-4-ENE-3,11,20-TRIONE 17ALPHA-HYDROXY-11-DEHYDROCORTICOSTERONE 17-HYDROXY-11-DEHYDROCORTICOSTERONE 4-PREGEN-17A,21-DIOL-3,11,20-TRIONE 4-PREGNEN-17,21-DIOL-3,11,20-TRIONE 4-PREGNEN-17ALPHA,21-DIOL-3,11,20-TRIONE 4-PREGNENE-17ALPHA,21-DIOL-3,11,20-TRIONE CORTISONE CORTONE DELTA4-PREGNENE-17, 21-DIOL-3, 11, 20-TRIONE DELTA4-PREGNENE-17ALPHA,21-DIOL-3,11,20-TRIONE DELTA-PREGNENE-17ALPHA,21-DIOL-3,11,20-TRIONE KENDALL'S CMPD ''E'' KENDALL'S COMPOUND E KENDALL'S COMPOUND 'E' KENDALL'S ''E'' REICHSTEIN'S COMPOUND ''FA'' |
| CAS NO | 53-06-5 |
| EINECS(EC#) | 200-162-4 |
| Molecular Formula | C21H28O5 |
| MDL Number | MFCD00003610 |
| Molecular Weight | 360.44 |
| MOL File | 53-06-5.mol |
| CORTISONE Chemical Properties | |
|---|---|
| Melting point | 223-228 °C (dec.)(lit.) |
| alpha | D25 +209° (c = 1.2 in 95% alcohol); 25546 +269° (c = 0.125 in benzene); 25546 +248° (c = 0.1 to 0.2 in alcohol) |
| Boiling point | 412.46°C (rough estimate) |
| density | 1.28±0.1 g/cm3 (20 ºC 760 Torr) |
| refractive index | 210 ° (C=1, EtOH) |
| storage temp | -20°C Freezer |
| Fp | 9℃ |
| pka | 12.37±0.60(Predicted) |
| Water Solubility | 229.9mg/L(25 ºC) |
| Merck | 2539 |
| CAS DataBase Reference | 53-06-5(CAS DataBase Reference) |
| Safety Information | |
|---|---|
| Hazard Codes | F,T,Xn |
| Risk Statements | 11-23/24/25-39/23/24/25-63 |
| Safety Statements | 22-24/25-45-36/37-16-7 |
| WGK Germany | 3 |
| RTECS | GM9020000 |
| HS Code | 2937210000 |
| F | 18 |
| RIDADR | UN1230 - class 3 - PG 2 - Methanol, solution |
| CORTISONE Usage And Synthesis | |
|---|---|
| Chemical Properties | Off-White Crystalline Powder |
| Definition | ChEBI: A C21-steroid that is pregn-4-ene substituted by hydroxy groups at positions 17 and 21 and oxo group at positions 3, 11 and 20 |
| Uses | Glucocorticoid, anti-inflammatory agent |
| Uses | antiinflammatory, glucocorticoid |
| Uses | Anticoagulant |
| Hazard | Damaging side effects, e.g., sodium retention from ingestion |
| Pharmacokinetics | Following oral administration, cortisone acetate and hydrocortisone acetate are completely and rapidly deacetylated by first-pass metabolism. Much of the oral cortisone, however, is inactivated by oxidative metabolism before it can be converted to hydrocortisone in the liver. The pharmacokinetics for hydrocortisone acetate is indistinguishable from that of orally administered hydrocortisone. Oral hydrocortisone is completely absorbed, with a bioavailability of greater than 95% and a half-life of 1 to 2 hours (23). |
| Clinical Use | Cortisone is administered orally or by intramuscular (IM) injection as its 21-acetate (cortisone acetate). Cortisone acetate or hydrocortisone usually is the corticosteroid of choice for replacement therapy in patients with adrenocortical insufficiency, because these drugs have both glucocorticoid and mineralocorticoid properties. |
| Metabolism | The metabolism of hydrocortisone has been previously described. Cortisone acetate is slowly absorbed from IM injection sites over a period of 24 to 48 hours and is reserved for patients who are unable to take the drug orally. The acetate ester derivative demonstrates increased stability and has a longer duration of action when administered by IM injection. Thus, smaller doses can be used. Similarly, hydrocortisone may be dispensed as its 21-acetate (hydrocortisone acetate), which is superior to cortisone acetate when injected intra-articularly. |
| Purification Methods | Crystallise cortisone from 95% EtOH or acetone. The UV has 14,000 M-1cm -1 at 237nm (EtOH). [Beilstein 8 IV 3480, Hems J Pharm Pharmacol 5 409 1953, Beilstein 8 IV 3480.] |
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