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Fluticasone Propionate

HCID 178916017
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Grundinformationen

CAS
192191-51-8
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

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 Impurity 5
Summenformel
C49H60F4O10S2
Molmasse
949.12

Namen und Synonyme

FLUTICASONE PROPIONATE80474-14-2FloventCutivateFlixotideFlonaseFlovent HFAFlovent DiskusFlovent Diskus 50Flovent Diskus 100Flovent Diskus 250Xhance
Weitere Namen anzeigen
Fluticasone Impurity 5Fluticasone Propionate-CH2 DimerFluticasone Propionate Impurity 24Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-, S,S′-methylene ester, (6α,11β,16α,17α)-(6′α,11′β,16′α,17′α)-6α,11β,16α,17α)-(6'α,11'β,16'α,17'α)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-,S,S’-methylene ester, (9CI) androsta-1,4-diene-17-carbothioic acidAndrosta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-, S,S'-methylene ester, (6α,11β,16α,17α)-(6'α,11'β,16'α,17'α)- (9CI)(6S,6''S,8S,8''S,9R,9''R,10S,10''S,11S,11''S,13S,13''S,14S,14''S,16R,16''R,17R,17''R)-((Methylenebis(sulfanediyl))bis(carbonyl))bis(6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17,17-diyl) Dipropionate

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 · 2 Einträge

Pharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations

Pharmaceuticals -> Listed in ZINC15

SolubilityInsoluble
Human Drugs · 3 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point261-273 °C
Physical DescriptionSolid

Physikochemische Eigenschaften

Siedepunkt
892.6 · 892.6±65.0 °C(Predicted)
Dichte
1.37 · 1.37±0.1 g/cm3(Predicted)
pka
12.23 · 12.23±0.70(Predicted)

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 · 5 Einträge

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 · 2 Einträge

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%)

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 · 6 Einträge

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 · 4 Einträge

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)

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
(6S,6'S,8S,8'S,9R,9'R,10S,10'S,11S,11'S,13S,13'S,14S,14'S,16R,16'R,17R,17'R)-((Methylenebis(sulfanediyl))bis(carbonyl))bis(6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17,17-diyl) dipropionate (Fluticasone impurity)
CCI-18781ArmonAir RespiClickCCI 18781DTXSID8045511Fluticasone-17-propionateO2GMZ0LF5Wcci18781Flonase Allergy Relief

Datenbank-Bezeichner

CAS
192191-51-8
ChEMBL
CHEMBL1473
ChEBI
CHEBI:31441
UNII
O2GMZ0LF5W
EC Number
617-082-4
Nikkaji
J457.058H
Absorption, Distribution and Excretion · 4 Einträge

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

Verwenden6α,11β,16α,17α)-(6''α,11''β,16''α,17''α)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-,S,S’-methylene ester, (9CI) androsta-1,4-diene-17-carbothioic acid is used in the preparation of Fluticasone propionate (F599500).