Grundinformationen
- CAS
23674-86-4- Standard-SMILES
CCCC(=O)O[C@]1(C(=O)COC(C)=O)CC[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
WYQPLTPSGFELIB-JTQPXKBDSA-N- Summenformel
- C27H34F2O7
- Durchschnittliche Molmasse
- 508,5 g/mol
- Monoisotopische Masse
- 508,22725987
Überblick
Difluprednate is a corticosteroid hormone and a butyrate ester.
Namen und Bezeichner
- Bevorzugter Name
- Difluprednate
- IUPAC
- [(6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] butanoate
- Lokaler Name
- Difluprednat
- Englischer Name
- Difluprednate
- Summenformel
- C27H34F2O7
- Molmasse
- 508.55
Namen und Synonyme
difluprednate23674-86-4DurezolDFBADifluprednatoEpitopicDifluprednatumDTXSID0046773Difluoroprednisolone butyrate acetateS8A06QG2QEW 6309W-6309
Weitere Namen anzeigen
Difluprenatew6309myserDifluprednate-d5Difluprednate-d3
CM 9155[(6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] butanoateDTXCID80267736-alpha,9-alpha-Difluoroprednisolone 17-butyrate 21-acetate21-(Acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)pregna-1,4-diene-3,20-dione (6alpha,11beta)-Pregna-1,4-diene-3,20-dione, 6-alpha,9-difluoro-11-beta,17,21-trihydroxy-, 21-acetate, 17-butyrate((6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta(a)phenanthren-17-yl) butanoate(1R,2S,8S,10S,11S,14R,15S,17S)-14-(2-(acetyloxy)acetyl)-1,8-difluoro-17-hydroxy-2,15-dimethyl-5-oxotetracyclo(8.7.0.0^(2,7).0^(11,15))heptadeca-3,6-dien-14-yl butanoate
Datenbank-Bezeichner
- CAS
23674-86-4
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,4
- Polarare Oberfläche (TPSA)
- 107 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 9
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 36
- Formalladung
- 0
- Komplexität
- 1.050
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Dermatologicals -> Corticosteroids, dermatological preparations
Pharmaceuticals -> Listed in ZINC15
Human Drugs
Breast Feeding; Lactation; Anti-Inflammatory Agents; Corticosteroids, Ophthalmic; Glucocorticoids;
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point191-194
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 191 · 191-194°
- Siedepunkt
- 600.3 · 600.3±55.0 °C(Predicted)
- Dichte
- 1.1869 · 1.1869 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Dioxane (Slightly), Methanol (Slightly)
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
This chemical does not meet GHS hazard criteria for 20% (1 of 5) of reports.
Danger
H302+H312+H332 (20%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P203, P260, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P319, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesRepr. 1B (20%)
Toxikologische Informationen
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Sicherheitsdaten
- wgk
- 2
- hs_code
- 2937.29.9095
- RTECS-Nr.
- TU3831500
- Toxizität
- mouse,LD50,intraperitoneal,146mg/kg (146mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)BEHAVIORAL: FOOD INTAKE (ANIMAL),Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 15, Pg. 1066, 1984.
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
ATC Code
D - Dermatologicals
S - Sensory organs
QD - Dermatologicals
QS - Sensory organs
PharmacodynamicsDifluprednate is a corticosteroid used as an anti-inflammatory steroidal drug used primarily in ocular surgery.
Mechanism of Action
Corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins (lipocortins). It is postulated that these proteins control the biosynthesis of potent mediators of infammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2.
Metabolism/Metabolites
Difluprednate is rapidly deacetylated in the aqueous humor to difluoroprednisolone butyrate (DFB), the drug’s active metabolite. Endogenous tissue esterases then metabolize DFB to the inert metabolite hydroxyfluoroprednisolone butyrate (HFB), which limits systemic exposure to the active compound.
MeSH Pharmacological Classification
A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system.
Absorption, Distribution and Excretion
Difluprednate penetrates the corneal epithelium rapidly and effectively. Low systemic absorption.
78.5% of radioactivity was excreted aftert 24 hours, and 99.5% by 7 days after a single dose of labeled difluprednate instilled in the right eyes of pigmented rabbits.
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