Fluticasone Propionate
FLOVENT · Fluticasone propionate for impurity C identification CRS · CUTIVATE · Fluticasone propionate for impurity C identification · Zoflut · flutide · FLUNASE · FLONASE
Identifikatoren & physikalische Daten
| CAS No. | 80474-14-2 |
|---|---|
| Summenformel | C25H31F3O5S |
| Durchschnittliche Molmasse | 500,6 g/mol |
| Monoisotopische Masse | 500,18442975 g/mol |
| SMILES | CCC(=O)O[C@]1(C(=O)SCF)[C@H](C)C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C |
| InChIKey | WMWTYOKRWGGJOA-CENSZEJFSA-N |
| PubChem CID | 444036 |
| ChEMBL | CHEMBL1473 |
| ChEBI | CHEBI:31441 |
| EC No. | 617-082-4 |
| DTXSID | DTXSID8045511 |
Chemische & physikalische Eigenschaften
| XLogP | 4 |
|---|---|
| Polarare Oberfläche (TPSA) | 106 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 9 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 34 |
| Formalladung | 0 |
| Komplexität | 984 |
| Arzneimittel | Pharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparationsPharmaceuticals -> Listed in ZINC15 |
| Löslichkeit | InsolubleDMSO: ≥10 mg/mL |
| Human Drugs | FDA approved drugs -> Active ingredientPharmaceuticals |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 261-273 °C275 °C |
| Physical Description | Solid |
| Siedepunkt | 568.3±50.0 °C(Predicted) |
| Dichte | 1.32±0.1 g/cm3(Predicted) |
| Brechungsindex | 31 ° (C=1, Dioxane) |
| Lagerbedingungen | Store at RT |
| pKa (Säurekonstante) | 12.53±0.70(Predicted) |
| Aggregatzustand | solid |
| Farbe | white |
| Merck | 14,4211 |
| InChIKey | WMWTYOKRWGGJOA-CENSZEJFSA-N |
| SMILES | [C@]1(C(=O)SCF)(OC(=O)CC)[C@H](C)C[C@@]2([H])[C@]3([H])C[C@@H](C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)F |&1:0,11,14,16,19,26,28,30,33,r| |
| CAS Datenbank | 80474-14-2(CAS DataBase Reference) |
| EPA chemische Informationen | Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-,S-(fluoromethyl) ester, (6.alpha.,11.beta.,16.alpha.,17.alpha.)- (80474-14-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 10% (2 of 20) of reports.DangerH302 (20%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P233, P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P318, P319, P321, P330, P333+P317, P342+P316, P362+P364, P391, P403, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 20 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Hazard Traits - Developmental ToxicityFluticasone propionate: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Acute Tox. 4 (20%) |
| Wassergefährdungsklasse (WGK) | 2 |
| Zollcode | 29372900 |
| RTECS-Nr. | BV7980000 |
| Toxizität | LD50 oral in rat: > 2gm/kg |
| Sicherheitshinweise (S) | 22-24/25 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Repr. 2STOT RE 2 |
Anwendungen & Verwendung
Verwenden
Fluticasone Propionate is a derivative of Flumethasone, a glucocorticoid that has antiallergic, anti-asthmatic, and anti-inflammatory properties. It is used in the treatment of seasonal rhinitis and asthma. Compared to beclomethasone dipropionate, fluticasone propionate is reported to have a comparable side effect profile, but twice the activity in the treatment of asthma.
Herstellung & Synthese
synthetische
Fluticasone propionate, synthesized by Glaxo Wellcome and launched in 1993, is a trifluorinated glucocorticosteroid. It shows good topical antiinflammatory activity and is commonly used as a safe and effective inhaled treatment for asthma and allergic rhinitis.Fluticasone propionate can be synthesized from 9 by using BrCH2F,2a ClCH2F,5a or S-(monofluoromethyl) diarylsulfonium tetrafluoroborate 5f,g directly. Using BrCH2F can get an ideal yield; however, BrCH2F is costly and will destroy to the ozone layer. In addition, 9 reacted with BrCH2Cl or Br2CH2 and then by an anion exchange with AgF,2c,5e KF, or tetrabutylammonium fluoride5b to afford 1 in a low yield.Improved Synthesis of Fluticasone Propionate