Grundinformationen
- Standard-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- Summenformel
- C25H31F3O5S
- Durchschnittliche Molmasse
- 500,6 g/mol
- Monoisotopische Masse
- 500,18442975
Überblick
Fluticasone Propionate can cause developmental toxicity according to state or federal government labeling requirements.
Namen und Bezeichner
- Bevorzugter Name
- Fluticasone Propionate
- IUPAC
- [(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
- Englischer Name
- Fluticasone propionate
- Summenformel
- C25H31F3O5S
- Molmasse
- 500.57
Namen und Synonyme
FLUTICASONE PROPIONATE80474-14-2FloventCutivateFlixotideFlonaseFlovent HFAFlovent DiskusFlovent Diskus 50Flovent Diskus 100Flovent Diskus 250Xhance
Weitere Namen anzeigen
Fluticasone propionate for impurity C identification CRSFluticasone propionate for impurity C identificationZoflutflutideFLUNASEFLIXONASE
CCI-18781ArmonAir RespiClickCCI 18781DTXSID8045511Fluticasone-17-propionateO2GMZ0LF5Wcci18781Flonase Allergy Relief
Datenbank-Bezeichner
- CAS
80474-14-2- PubChem CID
- 444036
- DTXSID
DTXSID8045511- ChEMBL
CHEMBL1473- ChEBI
CHEBI:31441- UNII
- O2GMZ0LF5W
- EC Number
- 617-082-4
- Nikkaji
- J457.058H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4
- Polarare Oberfläche (TPSA)
- 106 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 9
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 34
- Formalladung
- 0
- Komplexität
- 984
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations
Pharmaceuticals -> Listed in ZINC15
SolubilityInsoluble
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point261-273 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 275 °C · 275 °C
- Siedepunkt
- 568.3 · 568.3±50.0 °C(Predicted)
- Dichte
- 1.32 · 1.32±0.1 g/cm3(Predicted)
- Brechungsindex
- 31 ° · 31 ° (C=1, Dioxane)
- storage temp.
- Store at RT
- Löslichkeit
- 10 mg/mL · DMSO: ≥10 mg/mL
- pka
- 12.53 · 12.53±0.70(Predicted)
- Aggregatzustand
- solid
- Farbe
- white
- Merck
- 14 · 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 · 80474-14-2(CAS DataBase Reference)
- EPA chemische Informationen
- -1 · 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 und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 10% (2 of 20) of reports.
Danger
H302 (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.
Gefahrenhinweise
Regulatory Information
Hazard Traits - Developmental Toxicity
Fluticasone propionate: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (20%)
Sicherheitsdaten
- wgk
- 2
- hs_code
- 29372900
- RTECS-Nr.
- BV7980000
- Toxizität
- LD50 oral in rat: > 2gm/kg
- safety_code
- 22-24/25
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Repr. 2STOT RE 2
Chemie und Industrie
Pharmakologische Informationen
Protein BindingFluticasone propionate is 99% protein bound in serum. Topical fluticasone propionate is only 91% protein bound in serum however.
PharmacodynamicsSystemically, fluticasone propionate activates glucocorticoid receptors, and inhibits lung eosinophilia in rats. Fluticasone propionate as a topical formulation is also associated with vasoconstriction in the skin.
Mechanism of ActionFluticasone propionate works through an unknown mechanism to affect the action of various cell types and mediators of inflammation. Fluticasone propionate activates glucocorticoid receptors and inhibits lung eosinophilia in rats.
Biological Half-Life7.8 hours for intravenous fluticasone propionate. A study of 24 healthy Caucasian males shows a half life of 14.0 hours following intravenous administration and 10.8 hours following inhalation.
Metabolism/MetabolitesFluticasone propionate is cleared from hepatic metabolism by cytochrome P450 3A4. Fluticasone propionate is hydrolysed at the FIVE-S-fluoromethyl carbothioate group, forming an inactive metabolite.
FDA Pharmacological Classification
FLUTICASONE PROPIONATE
Corticosteroid Hormone Receptor Agonists [MoA]; Corticosteroid [EPC]
ALLERGY RELIEF NASAL
Corticosteroid Hormone Receptor Agonists [MoA]; Corticosteroid [EPC]
FLUTICASONE PROPIONATE NASAL
Corticosteroid Hormone Receptor Agonists [MoA]; Corticosteroid [EPC]
MeSH Pharmacological Classification
Substances that reduce or suppress INFLAMMATION.
Agents that cause an increase in the expansion of a bronchus or bronchial tubes.
Drugs used to treat or prevent skin disorders or for the routine care of skin.
Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)
Absorption, Distribution and Excretion
Intranasal bioavailability of fluticasone propionate is <2%, and oral bioavailability is <1%. Intranasal exposure results in the majority of the dose being swallowed. Topical absorption of fluticasone propionate is very low but can change depending on a number of factors including integrity of the skin and the presence of inflammation or disease. A study of 24 healthy Caucasian males showed an inhaled bioavailability of 9.0%.
Fluticasone propionate is mainly eliminated in the feces with <5% eliminated in the urine.
The volume of distribution of intravenous fluticasone propionate is 4.2L/kg. A study of 24 healthy Caucasian males showed a volume of distribution at steady state of 577L following intravenous administration.
1093mL/min for fluticasone propionate. A study of 24 healthy Caucasian males showed a clearance of 63.9L/h following intravenous administration.
Cellular LocationsExtracellular
Verwendung und Herstellung
Use ClassificationPharmaceuticals
Anwendungen
VerwendenFluticasone 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.
Darstellung
synthetischeFluticasone 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
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Ergänzende Hinweise
DefinitionChEBI: Fluticasone propionate is a trifluorinated corticosteroid that consists of 6alpha,9-difluoro-11beta,17alpha-dihydroxy-17beta-{[(fluoromethyl)sulfanyl]carbonyl}-16-methyl-3-oxoandrosta-1,4-diene bearing a propionyl substituent at position 17; has anti-inflammatory, anti-asthmatic and anti-allergic activity. It has a role as an anti-allergic agent, an anti-asthmatic drug, an anti-inflammatory drug, a dermatologic drug, a bronchodilator agent and an adrenergic agent. It is a corticosteroid, a steroid ester, an 11beta-hydroxy steroid, a propanoate ester, a fluorinated steroid, a thioester and a 3-oxo-Delta(1),Delta(4)-steroid. It derives from a fluticasone. It derives from a hydride of an androstane.
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