Medroxyprogesteron

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H361：Kann vermutlich die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen.

• Sicherheit

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

MEDROXYPROGESTERONE Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R48:Gefahr ernster Gesundheitsschäden bei längerer Exposition.
  R63:Kann das Kind im Mutterleib möglicherweise schädigen.
  R68:Irreversibler Schaden möglich.

• S-Sätze Betriebsanweisung:

  S22:Staub nicht einatmen.
  S24/25:Berührung mit den Augen und der Haut vermeiden.

• Chemische Eigenschaften

  MEDROXYPROGESTERONE is White Solid

• Originator

  Provera,Upjohn,US,1959

• Verwenden

  An orally active progestogen used in hormone replacement therepy (HRT), in the past has been used as a component of oral contraceptives.SMedroxyprogesterone Acetate USP Related Compound B.

• Verwenden

  MEDROXYPROGESTERONE is an orally active progestogen used in hormone replacement therepy (HRT), in the past has been used as a component of oral contraceptives.

• Definition

  ChEBI: A 3-oxo Delta4-steroid that is pregn-4-ene-3,20-dione substituted by an alpha-hydroxy group at position 17 and a methyl group at position 6.

• Manufacturing Process

  Preparation of 17α-Hydroxyprogesterone 3,20-Bis-(Ethylene Ketal): A solution was prepared containing 50.0 g of 17α-hydroxyprogesterone in 1,000 ml of benzene, 100 ml of ethylene glycol and 2.5 g of p-toluenesulfonic acid monohydrate. This mixture was refluxed for a period of 17 hours using a calcium carbide water-trap to remove the water formed in the reaction. After this period of reflux 6.5 ml of pyridine was added to the solution, and the mixture cooled to room temperature.
  The lower glycol layer was separated and washed with benzene. The benzene layer and the benzene washings were combined and the combined solution was divided into two equal portions, one of which was used for the isolation of 17α-hydroxyprogesterone 3,20-bis-(ethylene ketal) as follows. The benzene solution was washed with 5% sodium carbonate solution, water and saturated sodium chloride solution. After being dried over anhydrous magnesium sulfate the solution was concentrated to dryness at reduced pressure, The residue was recrystallized by taking up in hot methylene chloride, adding acetone and boiling to remove the methylene chloride until a final volume of about 200 ml was reached.
  The solution was then refrigerated overnight and 17.8 g of crystals were removed by filtration. A second crop was obtained yielding 3.7 g of compound. The total yield of 17α-hydroxyprogesterone 3,20-bis-(ethylene ketal) was 20.3 g (64.3% of theory). Recrystallization of the crude 17αhydroxyprogesterone 3,20-bis-(ethylene ketal) from methanol gave the pure bisketal of MP 209° to 211°C.
  Preparation of 5α,6α-Oxido-17α-Hydroxyallopregnane-3,20-dione 3,20-Bis- (Ethylene Ketal): A solution was prepared by heating 19.96 g (0.0477 mol) of 17α-hydroxyprogesterone 3,20-bis-(ethylene ketal) and 500 ml of benzene. After the solution was effected the flask was cooled to 5°C and a mixture of 3.68 g (0.0449 mol) of sodium acetate and 174 ml of 40% peracetic acid was added with stirring. The reaction mixture was stirred in the ice bath for 3 hours. The lower peracid layer was separated, diluted with water and extracted twice with benzene.
  The upper layer was neutralized by the addition of cold 10% sodium hydroxide solution while stirring in an ice bath. The rate of addition of the sodium hydroxide was regulated to keep the temperature below 10°C. The benzene extracts from the peracid layer were combined and washed with cold 10% sodium hydroxide solution and with saturated sodium chloride solution. All the aqueous layers were washed again with the same portion of benzene. The combined benzene layers were dried over anhydrous magnesium sulfate and concentrated to dryness at reduced pressure.
  The residue was recrystallized from acetone using methylene chloride to aid in solution. The crystalline material was removed by filtration and was recrystallized from methylene chloride-acetone to yield a total of 8 g of 5α,6αoxido-17α-hydroxyallopregnane-3,20-dione 3,20-bis-(ethylene ketal) of MP 211° to 215°C. For analytical purposes, another recrystallization from methylene chloride-acetone gave pure 5α,6α-oxido-17α-hydroxyallopregnane3,20-dione 3,20-bis-(ethylene ketal) of MP 216° to 218.5°C.
  Preparation of 5α,17α-Dihydroxy-6β-Methylallopregnane-3,20-dione 3,20-bis- (Ethylene Ketal): To a solution of 91.6 g of 5α,6α-oxido-17αhydroxyallopregnane-3,20-dione 3,20-bis-(ethylene ketal) in 3,500 ml of freshly distilled tetrahydrofuran was added 1,170 ml of commercial 3 molar methyl magnesium bromide in ether solution. The reaction mixture was boiled to remove 1,800 ml of solvent by distillation and thereafter 1,000 ml of freshly distilled tetrahydrofuran was added.
  Boiling was continued under reflux for a period of 16 hours. The solution was then concentrated to about one-half its original volume by distillation and was poured slowly with vigorous stirring into a large volume of ice water containing 340 g of ammonium chloride. The aqueous solution was saturated with sodium chlo

• Trademarks

  Amen (Amarin); Curretab (Solvay Pharmaceuticals); Cycrin (ESI); Provera (Pharmacia & Upjohn).

• Therapeutic Function

  Progestin

• läuterung methode

  If it contains the epi-isomer (TLC), then dissolve it in CHCl3, bubble dry HCl gas to epimerise it, evaporate and recrystallise it from chloroform. The UV has max at 241nm ( 16,150) in EtOH. The 17-acetate [71-58-9] crystallises from MeOH with m 207-208o and [] D 25 +61o (CHCl3). Its UV has max at 240nm ( 15,950) in EtOH. [Babcock et al. J Am Chem Soc 80 2904 1958, Beilstein 8 IV 2212.]

MEDROXYPROGESTERONE Upstream-Materialien And Downstream Produkte

Medroxyprogesteron Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(163)Suppliers

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