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Prostaglandin E2

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Prostaglandin E2 Basic information
Prostaglandin E2 Chemical Properties
  • Melting point:66-68 °C
  • alpha -85.5 º (c=1, C2H5OH)
  • Boiling point:406.07°C (rough estimate)
  • Density 1.0601 (rough estimate)
  • refractive index 1.6120 (estimate)
  • storage temp. −20°C
  • solubility ethanol: 1 mg/mL
  • pkapKa 4.77± 0.09(H2O,t=25±0.1,I=0.1(NaCl)) (Uncertain)
  • form powder
  • color Clear yellow to amber
  • Water Solubility insoluble
  • Merck 14,7877
  • BRN 4709356
  • InChIKeyXEYBRNLFEZDVAW-ARSRFYASSA-N
  • CAS DataBase Reference363-24-6(CAS DataBase Reference)
Safety Information
MSDS
Prostaglandin E2 Usage And Synthesis
  • Chemical PropertiesWhite to pale yellowish-cream powder
  • OriginatorProstin E2,Upjohn,UK,1972
  • UsesThe most common and most biologically potent of mammalian prostaglandins. Isolated from sheep prostate. Oxytocic; abortifacient.
  • DefinitionChEBI: Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostagland ns.
  • Manufacturing ProcessHexamethyldisilazane (1 ml) and trimethylchlorosilane (0.2 ml) are added with stirring to a solution of PGA2 (250 mg) in 4 ml of tetrahydrofuran at 0°C under nitrogen. This mixture is maintained at 5°C for 15 hours. The mixture is then evaporated under reduced pressure. Toluene is added and evaporated twice. Then the residue is dissolved in 6 ml of methanol, and the solution is cooled to -20°C. Hydrogen peroxide (0.45 ml; 30% aqueous) is added. Then, 1N sodium hydroxide solution (0.9 ml) is added dropwise with stirring at - 20°C. After 2 hours at -20°C, an additional 0.3 ml of the sodium hydroxide solution is added with stirring at -20°C. After another hour in the range -10°C to -20°C, an additional 0.1 ml of the sodium hydroxide solution is added. Then, 1.5 ml of 1 N hydrochloric acid is added, and the mixture is evaporated under reduced pressure. The residue is extracted with ethyl acetate, and the extract is washed successively with 1 N hydrochloric acid and
    ine, dried with anhydrous sodium sulfate and evaporated. The residue is dissolved in 5 ml of diethyl ether. To this solution is added 0.5 ml of methanol and 0.1 ml of water. Amalgamated aluminum made from 0.5 g of aluminum metal is then added in small portions during 3 hours at 25°C. Then, ethyl acetate and 3 N hydrochloric acid are added, and the ethyl acetate layer is separated and washed successively with 1 N hydrochloric acid and
    ine, dried with anhydrous sodium sulfate, and evaporated. The residue is chromatographed on 50 g of acid-washed silica gel, eluting first with 400 ml of a gradient of 50- 100% ethyl acetate in Skellysolve B, and then with 100 ml of 5% methanol in ethyl acetate, collecting 25 ml fractions. Fractions 9 and 10 are combined and evaporated to give 18 mg of 11β-PGE2. Fractions 17-25 are combined and evaporated to give 39 mg of PGE2.
  • brand nameCervidil (Controlled Therapeutics); Prepidil (Pharmacia & Upjohn); Prostin E2 (Pharmacia & Upjohn);Minprostin;Prostaglandin;Prostarmon e;Prostin vr pediatric.
  • Therapeutic FunctionOxytocic, Abortifacient
  • World Health Organization (WHO)Dinoprostone, prostaglandin E2, was introduced into medicine in 1971 and is primarily used for cervical ripening during the induction of labour. It is available in various formulations for oral, parenteral and vaginal administration. Tablets, ampoules and vaginal dosage forms (tablets, pessaries, gel) remain registered in many countries.
  • General DescriptionPGE2 Dinoprostone (Prostin E2;Cervidil) is a naturally occurring prostaglandin that is administeredin a single dose of 10 mg by controlled-release(0.3 mg/hr) vaginal insert to induce cervical ripening. Use ofthis agent will potentiate the effects of oxytocin.
  • Biological ActivityEndogenous prostaglandin and primary product of arachidonic acid/cyclooxygenase pathway. Binds with high affinity to EP 1 , EP 2 , EP 3 and EP 4 receptors (K d values range between ~ 1-10 nM). Influences a wide range of processes including inflammation, smooth muscle relaxation, fertility and gastric mucosal integrity. Regulates vertebrate hematopoietic stem cell (HSC) homeostasis.
  • Safety ProfilePoison by subcutaneous and intravenous routes. Moderately toxic by ingestion and intraperitoneal routes. An experimental teratogen. Human reproductive effects by intravenous, intraplacental, and intravaginal routes: changes in the uterus, cervix and vagina; termination of pregnancy; and changes in ferthty. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Prostaglandin E2 Preparation Products And Raw materials
Prostaglandin E2 (363-24-6)Related Product Information
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