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Betamethasone 17-valerate

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Betamethasone 17-valerate Basic information
Betamethasone 17-valerate Chemical Properties
  • Melting point:183-184°
  • alpha D +77° (dioxane)
  • Boiling point:598.9±50.0 °C(Predicted)
  • Density 1.1174 (estimate)
  • storage temp. 2-8°C
  • solubility Practically insoluble in water, freely soluble in acetone and in methylene chloride, soluble in ethanol (96 per cent).
  • form neat
  • pka12.90±0.70(Predicted)
  • Merck 13,1183
  • BRN 4240001
  • InChIKeySNHRLVCMMWUAJD-SUYDQAKGSA-N
  • CAS DataBase Reference2152-44-5(CAS DataBase Reference)
  • EPA Substance Registry System.beta.-Methasone 17-valerate (2152-44-5)
Safety Information
  • Hazard Codes Xn
  • Risk Statements 48
  • Safety Statements 22-24/25
  • RTECS TU3835000
  • HS Code 2937229000
MSDS
Betamethasone 17-valerate Usage And Synthesis
  • Chemical PropertiesWhite Solid
  • OriginatorValisone,Schering,US,1967
  • UsesBetamethasone 17-Valerate is a corticosteroid with anti-inflammatory properties. Topical application of Betamethasone 17-Valerate has been shown to inhibit heat-induced vasodilatation in man.
  • UsesAntiepileptic non-selective phosphodiesterase inhibitor
  • UsesBetamethasone 17-valerate is a glucocorticoid with anti-inflammatory and immunosuppressive activity.
  • UsesA potent glucocorticoid steroid with anti-inflammatory and immunosuppressive properties
  • DefinitionChEBI: A steroid ester that is betamethasone in which the hydroxy group at the 17alpha position has been converted to the corresponding pentanoate ester.
  • IndicationsBetamethasone valerate (Psorion, Beta-Val, Luxiq) is a synthetic fluorinated corticosteroid.
  • Manufacturing ProcessThe valerate is made from betamethasone as a starting material as follows: A suspension of 9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene- 3,20-dione(betamethasone) (2 grams) in sodium dried benzene (500 ml) was distilled vigorously for a few minutes, toluene-p-sulfonic acid monohydrate (30 mg) and methyl orthovalerate (5 ml) were added and distillation was continued for 10 minutes. The mixture was then boiled under reflux for 1.5 hours after which time unreacted betamethasone alcohol (400 mg) was removed by filtration. The benzene solution was treated with solid sodium .bicarbonate and a few drops of pyridine, filtered and evaporated to dryness at about 50°C. The residue, in ether, was filtered through grade III basic alumina (20grams) to remove traces of unreacted betamethasone alcohol, the ether removed in vacuo and the residue of crude betamethasone 17,21- methyl orthovalerate was treated with acetic acid (20ml) and a few drops of water and left overnight at room temperature.
    The acetic acid solution was poured into water (100 ml) and extracted with chloroform. The chloroform extracts were washed in turn with water, saturated sodium bicarbonate solution and water, dried and evaporated in vacuo. The residual gum was triturated with ether and a white crystalline solid (1.16 grams) isolated by filtration. Recrystallization from ether (containing a small amount of acetone)-petroleum ether gave 9α-fluoro-11β,21-dihydroxy-16β- methyl-17α-valeryloxypregna-1,4-diene-3,20-dione (871 mg) as fine needles.
  • brand nameBetatrex (Savage); Luxiq (Connetics); Valisone (Schering).
  • Therapeutic FunctionCorticosteroid
Betamethasone 17-valerate(2152-44-5)Related Product Information
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