Grundinformationen
- Standard-SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO- InChIKey
MFYSYFVPBJMHGN-ZPOLXVRWSA-N- Summenformel
- C21H28O5
- Durchschnittliche Molmasse
- 360,4 g/mol
- Monoisotopische Masse
- 360,19367399
Namen und Bezeichner
- Bevorzugter Name
- Cortisone
- IUPAC
- (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione
- Lokaler Name
- Cortison
- Englischer Name
- CORTISONE
- Summenformel
- C21H28O5
- Molmasse
- 360.44
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
53-06-5- PubChem CID
- 222786
- DTXSID
DTXSID5022857- ChEMBL
CHEMBL1499- ChEBI
CHEBI:16962- UNII
- V27W9254FZ
- EC Number
- 200-162-4
- Nikkaji
- J4.139D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,5
- Polarare Oberfläche (TPSA)
- 91,7 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 724
Experimentelle und physikochemische Eigenschaften
Collision Cross Section
257.2 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID5022857]
180.07 Ų [M-H2O-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)];188.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
172.48 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];186.07 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];182.86 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
184 Ų [M+H]+ [CCS Type: TW]
184.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
213.2 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)];191.4 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)];188.3 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
Physikochemische Eigenschaften
- Schmelzpunkt
- 223 · 223-228 °C (dec.)(lit.)
- Siedepunkt
- 412.46 °C · 412.46°C (rough estimate)
- Dichte
- 1.28 · 1.28±0.1 g/cm3 (20 ºC 760 Torr)
- Brechungsindex
- 210 ° · 210 ° (C=1, EtOH)
- Flammpunkt
- 9 ℃ · 9℃
- storage temp.
- -20 °C · -20°C Freezer
- Löslichkeit
- Chloroform (Slightly, Heated, Sonicated), DMSO (Slightly), Ethanol (Slightly, Heated)
- Aggregatzustand
- Solid
- pka
- 12.37 · 12.37±0.60(Predicted)
- Farbe
- White to Pale Beige
- Wasserlöslichkeit
- 229.9 mg/L · 229.9mg/L(25 ºC)
- Merck
- 2539 · 2539
- Major Application
- clinical testingclinical testing
- InChIKey
- MFYSYFVPBJMHGN-ZPOLXVRWSA-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)CO
- LogP
- 1.47 · 1.470
- CAS Datenbank
- 53 · 53-06-5(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H361 (98%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 51 reports by companies from 5 notifications to the ECHA C&L Inventory.;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
Toxikologische Informationen
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Cortisone is a normal component of breastmilk that passes from the mother's bloodstream into milk and might have a role in intestinal maturation, the intestinal microbiome, growth, body composition or neurodevelopment, but adequate studies are lacking. Concentrations follow a diurnal rhythm, with the highest concentrations in the morning at about 7:00 am and the lowest concentrations in the late afternoon and evening. Cortisone has not been studied in breastmilk after exogenous administration in pharmacologic amounts. Although it is unlikely that dangerous amounts of cortisone would reach the infant, a better studied alternate drug might be preferred. Medium to large doses of corticosteroids given systemically or injected into joints or the breast have been reported to cause temporary reduction of lactation.;◉ Effects in Breastfed Infants;None reported with any corticosteroid.;◉ Effects on Lactation and Breastmilk;Published information on the effects of cortisone on serum prolactin or on lactation in nursing mothers was not found as of the revision date. Medium to large doses of corticosteroids given systemically or injected into joints or the breast have been reported to cause temporary reduction of lactation.;A study of 46 women who delivered an infant before 34 weeks of gestation found that a course of another corticosteroid (betamethasone, 2 intramuscular injections of 11.4 mg of betamethasone 24 hours apart) given between 3 and 9 days before delivery resulted in delayed lactogenesis II and lower average milk volumes during the 10 days after delivery. Milk volume was not affected if the infant was delivered less than 3 days or more than 10 days after the mother received the corticosteroid. An equivalent dosage regimen of cortisone might have the same effect.;A study of 87 pregnant women found that betamethasone given as above during pregnancy caused a premature stimulation of lactose secretion during pregnancy. Although the increase was statistically significant, the clinical importance appears to be minimal. An equivalent dosage regimen of cortisone might have the same effect.
Regulatorische Informationen
Sicherheitsdaten
- F
- 18
- wgk
- 3
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- hs_code
- 2937210000
- RTECS-Nr.
- GM9020000
- risk_code
- 11-23/24/25-39/23/24/25-63
- hazard_code
- F,T,Xn
- safety_code
- 22-24/25-45-36/37-16-7
- Speicherklasse
- 3 - Flammable liquids
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Chemie und Industrie
Pharmakologische Informationen
ATC Code
H - Systemic hormonal preparations, excl. sex hormones and insulins;H02 - Corticosteroids for systemic use;H02A - Corticosteroids for systemic use, plain;H02AB - Glucocorticoids;H02AB10 - Cortisone
S - Sensory organs;S01 - Ophthalmologicals;S01B - Antiinflammatory agents;S01BA - Corticosteroids, plain;S01BA03 - Cortisone
QH - Systemic hormonal preparations, excl. sex hormones and insulin;QH02 - Corticosteroids for systemic use;QH02A - Corticosteroids for systemic use, plain;QH02AB - Glucocorticoids;QH02AB10 - Cortisone
QS - Sensory organs;QS01 - Ophthalmologicals;QS01B - Antiinflammatory agents;QS01BA - Corticosteroids, plain;QS01BA03 - Cortisone
FDA Pharmacological Classification
V27W9254FZ
CORTISONE
Established Pharmacologic Class [EPC] - Corticosteroid
Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists
Cortisone is a Corticosteroid. The mechanism of action of cortisone is as a Corticosteroid Hormone Receptor Agonist.
Metabolite Pathways
11-beta-hydroxylase deficiency (CYP11B1);17-alpha-hydroxylase deficiency (CYP17);21-hydroxylase deficiency (CYP21);3-Beta-Hydroxysteroid Dehydrogenase Deficiency;Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency;Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency;Apparent mineralocorticoid excess syndrome;Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH;Corticosterone methyl oxidase I deficiency (CMO I);Corticosterone methyl oxidase II deficiency - CMO II;Total 11 pathways, visit the HMDB page for details
Verwendung und Herstellung
Use Classification
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Pharmaceuticals -> Steroid hormones
Anwendungen
VerwendenCortisone is used for inflammatory processes, allergies, and adrenal insufficiency.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: 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.
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