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Desogestrel

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Desogestrel Basic information
Desogestrel Chemical Properties
  • Melting point:109-110°C
  • alpha D20 +55° (chloroform)
  • Boiling point:390.62°C (rough estimate)
  • Density 1.0169 (rough estimate)
  • refractive index 1.5100 (estimate)
  • storage temp. -20°C Freezer
  • solubility Practically insoluble in water, very soluble in methanol, freely soluble in anhydrous ethanol and in methylene chloride.
  • form neat
  • pka13.07±0.40(Predicted)
  • Merck 14,2926
Safety Information
MSDS
Desogestrel Usage And Synthesis
  • Chemical PropertiesWhite Solid
  • OriginatorDicromil,Organol ,W. Germany,1981
  • UsesA progestogen with low androgenic potency
  • Manufacturing ProcessA solution of 1.0 g of 11,11-methylene-18-methyl-delta4-estren-17-one in 33 ml tetrahydrofuran was added to a potassium-acetylide solution in tetrahydrofuran.
    After 2 hours of stirring at 0°C to 5°C the reaction mixture was acidified with 2N H2SO4and processed further.
    By a chromatographic treatment on silica gel and crystallization from pentane 0.7 g of 11,11-methylene-17α-ethynyl-18-methyl-δ4-estren-17β-ol with a melting point of 109°C to 110°C and an [α]D of +55°C (CHCl3) was obtained.
  • Therapeutic FunctionProgestin
  • General DescriptionDesogestrel, (17α)-13-ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol, is a 19-nortestosterone analog with good progestin activity. Likethe other progestins, it is orally active and used in combinationwith an estrogen in oral contraceptives. Desogestrel is aprodrug that must be oxidized to the 3-one in vivo to haveprogestational action. CYPs 2C9 and 2C19 have been implicatedin the initial hydroxylation of desogestrel at C3.
  • Clinical UseDesogestrel also is a prodrug and is rapidly metabolized in the intestinal mucosa and on first pass through the liver to its active metabolite, etonogestrel (3-ketodesogestrel). Following oral administration, the relative bioavailability for desogestrel is approximately 84%. Desogestrel also exhibits high selectivity for the progesterone receptor and low and rogenic activity, and it does not diminish the beneficial effects of estrogen on the lipid profile.
Desogestrel Preparation Products And Raw materials
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