Grundinformationen
- CAS
514-36-3- Standard-SMILES
CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C- InChIKey
SYWHXTATXSMDSB-GSLJADNHSA-N- Summenformel
- C23H31FO6
- Durchschnittliche Molmasse
- 422,5 g/mol
- Monoisotopische Masse
- 422,21046687
Überblick
Fludrocortisone acetate is an acetate ester resulting from the formal condensation of the primary hydroxy group of fludrocortisone with acetic acid. A synthetic corticosteroid, it has glucocorticoid actions about 10 times as potent as hydrocortisone, while its mineralocorticoid actions are over 100 times as potent. It is used in partial replacement therapy for primary and secondary adrenocortical insufficiency in Addison's disease and for the treatment of salt-losing adrenal hyperplasia. It is a tertiary alpha-hydroxy ketone, a mineralocorticoid, a 17alpha-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, an acetate ester, a 3-oxo-Delta(4) steroid and a fluorinated steroid. It is functionally related to a fludrocortisone.
Namen und Bezeichner
- Bevorzugter Name
- Fludrocortisone Acetate
- IUPAC
- [2-[(8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
- Lokaler Name
- Fludrocortison-21-acetat
- Englischer Name
- Fludrocortisone acetate
- Summenformel
- C23H31FO6
- Molmasse
- 422.49
Namen und Synonyme
FLUDROCORTISONE ACETATE514-36-3ScherofluronAlflorone acetateFlorinef acetateFludrocortisone 21-acetateCortef-FFluorocortisol acetateFluorocortisone acetateFluohydrocortisone acetate9alpha-Fluorohydrocortisone acetate9alpha-Fluorohydrocortisone 21-acetate
Weitere Namen anzeigen
9-FLUOROHYDROCORTISONE ACETATE9αNSC 15186cortineffalfloroneacetate9-FLUOROCORTISOL ACETATE
V47IF0PVH4U 4845NSC-15186Fludrocortisoni acetasDTXSID20230629-Fluoro-11beta,17,21-trihydroxypregn-4-ene-3,20-dione 21-acetateCHEBI:5102NSC15186
Datenbank-Bezeichner
- CAS
514-36-3- PubChem CID
- 225609
- DTXSID
DTXSID2023062- ChEMBL
CHEMBL1201010- ChEBI
CHEBI:5102- UNII
- V47IF0PVH4
- EC Number
- 208-180-4
- Nikkaji
- J6.287A
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,7
- Polarare Oberfläche (TPSA)
- 101 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 30
- Formalladung
- 0
- Komplexität
- 838
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section189.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 233 · 233-234°C
- Siedepunkt
- 575.1 · 575.1±50.0 °C(Predicted)
- Dichte
- 1.0953 · 1.0953 (rough estimate)
- Brechungsindex
- 1.598 · 1.5980 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Practically insoluble in water, sparingly soluble in anhydrous ethanol.
- pka
- 12.06 · 12.06±0.70(Predicted)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- 54 mg/L · 54mg/L(25 ºC)
- InChIKey
- UUHYILPJUKGJDI-XYNXPQAZSA-N
- SMILES
- F[C@]12[C@H](C[C@@]3([C@@](O)(C(=O)COC(=O)C)CC[C@@]3([H])[C@]1([H])CCC1=CC(=O)CC[C@]21C)C)O |&1:1,2,4,5,16,18,28,r|
- CAS Datenbank
- 514 · 514-36-3(CAS DataBase Reference)
- EPA chemische Informationen
- Fluorocortisone acetate (514-36-3)
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
H302 (95.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Other Safety InformationIMAP assessments - Pregn-4-ene-3,20-dione, 21-(acetyloxy)-9-fluoro-11,17-dihydroxy-, (11.beta.)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (95.2%)
Toxikologische Informationen
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Fludrocortisone acetate
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
EPA Human Health Benchmarks for Pharmaceuticals
Fludrocortisone acetate
0.001
0.004
The usual dose is 0.1 mg of fludrocortisone acetate tablets daily, although dosage ranging from 0.1 mg three times a week to 0.2 mg daily has been employed. In the event transient hypertension develops as a consequence of therapy, the dose should be reduced to 0.05 mg daily.
Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 0.043 mg/day, Lowest Therapeutic Dose (LTD): 0.0005 mg/kg-day, and Screening Dose: 0.0000002 mg/kg-day.
18-May-21
Sicherheitsdaten
- wgk
- 3
- hs_code
- 2937220000
- RTECS-Nr.
- TU5050000
- risk_code
- 63
- Toxizität
- LD50 oral in rat: > 1gm/kg
- hazard_code
- Xn
- safety_code
- 22-26-36
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 OralRepr. 2
Chemie und Industrie
Anwendungen
BeschreibungFludrocortisone acetate is the acetate form of the synthetic corticosteroid fludrocortisone, which is a mineralocorticoid receptor agonist. Fludrocortisone acetate (0.1-5 μg/animal) promotes sodium retention in rats in a dose-dependent manner with 37% of sodium excreted compared with control when used at a dose of 5 μg/animal. Formulations containing fludrocortisone acetate have been used in the treatment of Addison’s disease.
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Ergänzende Hinweise
DefinitionChEBI: An acetate ester resulting from the formal condensation of the primary hydroxy group of fludrocortisone with acetic acid. A synthetic corticosteroid, it has glucocorticoid actions about 10 times as potent as hydrocortisone, while its mineralocorticoid acti ns are over 100 times as potent. It is used in partial replacement therapy for primary and secondary adrenocortical insufficiency in Addison's disease and for the treatment of salt-losing adrenal hyperplasia.
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