Cortison-21-acetat
CORTISONE 21-ACETATE · 2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-diMethyl-3,11-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate · artriona · cortelan · cortisyl · ricortex · NSC 49420 · cortistab
Identifikatoren & physikalische Daten
| CAS No. | 50-04-4 |
|---|---|
| Summenformel | C23H30O6 |
| Durchschnittliche Molmasse | 402,5 g/mol |
| Monoisotopische Masse | 402,20423867 g/mol |
| SMILES | CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@@]21C |
| InChIKey | ITRJWOMZKQRYTA-RFZYENFJSA-N |
| PubChem CID | 5745 |
| ChEMBL | CHEMBL1650 |
| ChEBI | CHEBI:3897 |
| EC No. | 200-006-5 |
| DTXSID | DTXSID0022858 |
| Lokaler Name | Cortison-21-acetat |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 97,7 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 29 |
| Formalladung | 0 |
| Komplexität | 827 |
| LogP (Verteilungskoeffizient) | 2.12.10 |
| Löslichkeit | 202.78e-02 g/LPractically insoluble in water, freely soluble in methylene chloride, soluble in dioxan, sparingly soluble in acetone, slightly soluble in ethanol (96 per cent) and in methanol.19mg/L(25 ºC) |
| Schmelzpunkt | 227-229222 °C237-240 °C(lit.) |
| Physical Description | Solid |
| Collision Cross Section | 196.5 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 577.3±50.0 °C(Predicted) |
| Dichte | 1.26±0.1 g/cm3(Predicted) |
| Brechungsindex | 212 ° (C=1, MeOH) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 12.32±0.60(Predicted) |
| Farbe | White to Off-White |
| Merck | 14,2539 |
| BRN | 2067543 |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | pharmaceutical |
| InChIKey | ITRJWOMZKQRYTA-RFZYENFJSA-N |
| SMILES | O[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@]4(CCC(=O)C=C4CC3)C)C(=O)C2)CC1)C)C(=O)COC(=O)C |
| CAS Datenbank | 50-04-4(CAS DataBase Reference) |
| EPA chemische Informationen | Cortisone acetate (50-04-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH312 (73.9%): Harmful in contact with skin [Warning Acute toxicity, dermal]H332 (73.9%): Harmful if inhaled [Warning Acute toxicity, inhalation]H361 (87%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]P203, P261, P271, P280, P302+P352, P304+P340, P317, P318, P321, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 23 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 14-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21329Cortisone acetate: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Pregn-4-ene-3,11,20-trione, 21-(acetyloxy)-17-hydroxy-: Environment tier I assessmentIMAP assessments - Pregn-4-ene-3,11,20-trione, 21-(acetyloxy)-17-hydroxy-: Human health tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (73.9%)Repr. 2 (87%) |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Cortisone acetatevNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 32041200 |
| RTECS-Nr. | GM9140000 |
| Sicherheitshinweise (S) | 22-36/37-24/25 |
Anwendungen & Verwendung
Beschreibung
Cortisone acetate is a synthetic glucocorticoid with anti-inflammatory properties. It decreases the size of Bacillus Calmette-Guérin (BCG) vaccine-induced dermal lesions and tuberculin reactions in rabbits when administered at 2 mg/kg on alternate days over the course of 46 days. It also reduces the number and percentage of activated lesion-infiltrating mononuclear cells and decreases the amount of caseous necrosis and ulceration. Cortisone acetate (2.5 mg/kg per day, s.c.) slows tissue regeneration in a rabbit model of wound healing. It also decreases the number of dexamethasone binding sites on isolated human lymphocytes by 30%. Formulations containing cortisone acetate have been used to relieve inflammation, pruritic manifestations of corticosteroid-responsive dermatoses, and in the treatment of immune and allergic disorders.
Verwenden
Cortisone Acetate (Hydrocortisone Acetate EP Impurity D) is a glucocorticoid. Cortisone Acetate is an antiinflammatory agent. Cortisone Acetate is bioavailable and readily converted to the therapeutically active form, Hydrocotisone.
Herstellung & Synthese
synthetische
Cortisone acetate is prepared from dehydropregnenolone by epoxidation, Wolff's oxidation, mycoxidation, chromic acid oxidation, hydrogen bromide ring-opening, Raney's nickel-catalyzed debromination, iodination, and acetyloxy substitution.