Grundinformationen
- CAS
50-04-4- Standard-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- Summenformel
- C23H30O6
- Durchschnittliche Molmasse
- 402,5 g/mol
- Monoisotopische Masse
- 402,20423867
Namen und Bezeichner
- Bevorzugter Name
- Cortisone Acetate
- IUPAC
- [2-[(8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
- Lokaler Name
- Cortison-21-acetat
- Englischer Name
- Cortisone acetate
- Summenformel
- C23H30O6
- Molmasse
- 402.48
Namen und Synonyme
CORTISONE ACETATE50-04-4Cortisone 21-acetateCortone acetateCortisylCortelanCortistabPregn-4-ene-3,11,20-trione, 21-(acetyloxy)-17-hydroxy-Cortisone, 21-acetateCortisone aceticumDTXSID0022858NSC-49420
Weitere Namen anzeigen
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 acetateartrionaricortexNSC 49420biocortacetatecortoneacetate
17,21-Dihydroxypregn-4-ene-3,11,20-trione 21-acetate883WKN7W8X21-(Acetyloxy)-17-hydroxypregn-4-ene-3,11,20-trioneDTXCID502858NSC4942017alpha,21-dihydroxypregn-4-ene-3,11,20-trione acetate17-Hydroxy-3,11,20-trioxopregn-4-en-21-yl acetateRefChem:54895
Datenbank-Bezeichner
- CAS
50-04-4
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,1
- Polarare Oberfläche (TPSA)
- 97,7 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 827
Experimentelle und physikochemische Eigenschaften
LogP
2.1
2.10
Solubility
20
2.78e-02 g/L
Melting Point
227-229
222 °C
Physical DescriptionSolid
Collision Cross Section196.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 237 · 237-240 °C(lit.)
- Siedepunkt
- 577.3 · 577.3±50.0 °C(Predicted)
- Dichte
- 1.26 · 1.26±0.1 g/cm3(Predicted)
- Brechungsindex
- 212 ° · 212 ° (C=1, MeOH)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Practically 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.
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H312 (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.
Gefahrenhinweise
Regulatory Information
Status: Active Update: 14-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21329
Cortisone acetate: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Pregn-4-ene-3,11,20-trione, 21-(acetyloxy)-17-hydroxy-: Environment tier I assessment；IMAP assessments - Pregn-4-ene-3,11,20-trione, 21-(acetyloxy)-17-hydroxy-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (73.9%)；Acute Tox. 4 (73.9%)；Repr. 2 (87%)
Toxikologische Informationen
Chemie und Industrie
Pharmakologische Informationen
Protein BindingCorticosteroids are generally bound to corticosteroid binding globulin and serum albumin in plasma.
Pharmacodynamics
Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals. The duration of action is moderate as it is generally given once daily. Corticosteroids have a wide therapeutic window as patients may require doses that are multiples of what the body naturally produces. Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.
Mechanism of Action
The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation. Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days. Glucocorticoids inhibit neutrophil apoptosis and demargination; they inhibit phospholipase A2, which decreases the formation of arachidonic acid derivatives; they inhibit NF-Kappa B and other inflammatory transcription factors; they promote anti-inflammatory genes like interleukin-10. Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive. High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.
FDA Pharmacological Classification
CORTISONE ACETATE
Corticosteroid Hormone Receptor Agonists [MoA]; Corticosteroid [EPC]
MeSH Pharmacological ClassificationSubstances that reduce or suppress INFLAMMATION.
Absorption, Distribution and Excretion
Corticosteroids are eliminated predominantly in the urine.
Data regarding the clearance of cortisone acetate is not readily available.
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