Trimethadion

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H360：Kann die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen.

• Sicherheit

  P201：Vor Gebrauch besondere Anweisungen einholen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P308+P313：BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R61:Kann das Kind im Mutterleib schädigen.
  R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.

• S-Sätze Betriebsanweisung:

  S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
  S22:Staub nicht einatmen.
  S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
  S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).

• Chemische Eigenschaften

  White, granular, crystalline substance; camphor-like odor. Soluble in water; freely soluble in alcohol, chloroform, and ether; pH 6.0 (5% solution).

• Originator

  Tridione,Abbott,US,1946

• Verwenden

  Trimethadione is used in minor forms of epilepsy that does not respond to treatment of other drugs.

• Verwenden

  antifungal

• Verwenden

  3,5,5-Trimethyloxazolidine-2,4-dione is used in the control of absence (petit mal) seizures that are refractory to treatment with other medications. It is used in the treatment of epilepsy.

• Definition

  ChEBI: Trimethadione is an oxazolidinone that is 1,3-oxazolidine-2,4-dione substituted by methyl groups at positions 3, 5 and 5. It is an antiepileptic agent. It has a role as a geroprotector and an anticonvulsant.

• Manufacturing Process

  To a cooled solution of 23 parts of sodium in 400 parts of dry ethanol are added 60 parts of dry urea and 132 parts of ethyl α-hydroxy-isobutyrate. The mixture is heated on a steam bath under reflux for about 16 hours and the liberated ammonia is removed from the solution by drawing a current of dry air through it at the boiling point. The solution of the sodium salt of 5,5- dimethyloxazolidine-2,4-dione so obtained is cooled and treated with 284 parts of methyl iodide. The mixture is allowed to stand at room temperature for 3 days, excess methyl iodide and ethanol are then removed by distillation under reduced pressure.
  The residue is dissolved in ether and the solution is washed with sodium chloride solution and then with a little sodium thiosulfate solution. The ethereal solution is dried over sodium sulfate and ether removed by distillation. A yield of 108 parts of 3,5,5-trimethyloxazolidine-2,4-dione is obtained having a melting point of 45° to 46°C with slight softening at 43°C. This represents a 75% theory yield on the ethyl α-hydroxy-iso-butyrate taken. The product may be further purified by dissolving the minimum quantity of dry ether and cooling to -10°C. The product so obtained melts sharply at 45.5° to 46.5°C according to US Patent 2,559,011.

• Trademarks

  Absentol (Nourypharma), Epidione (Bellon), Ptimal (EGIS), Tridione/Trimedone (Abbott).

• Therapeutic Function

  Anticonvulsant

• Synthesis Reference(s)

  Tetrahedron, 51, p. 5891, 1995 DOI: 10.1016/0040-4020(95)00257-9

• Hazard

  May have adverse side effects; toxic in overdose.

• Clinical Use

  Trimethadione is indicated only for control of absence seizures refractory to treatment with other AEDs. It is ineffective against other seizure types. Trimethadione is a pro-drug and is metabolized by N-demethylation to dimethadione, which is effective in the pentylenetetrazole test, which acts by decreasing T-type calcium currents. Trimethadione is rapidly absorbed, is not protein bound, and has a half-life of 16 to 24 hours. The half-life of dimethadione, however, is substantially longer (i.e., 6–13 days), and dimethadione accumulates to concentrations greater than the parent drug. Because of its potentially fatal side effects. including aplastic anemia, nephrosis, idiosyncratic rashes, and exfoliative dermatitis, trimethadione rarely is used today.

• Synthese

  Trimethadione, 3,5,5-trimethyloxazolidine-2,4-dione (9.8.2), is synthesized by methylating 5,5-trimethyloxazolidine-2,4-dione (9.8.1) with dimethylsulfate.Starting 5,5-trimethyloxazolidine-2,4-dione (9.8.1) is in turn synthesized by the cyclocondensation of the ester of 2-hydroxyisobutyric acid with urea [26¨C28].

  

3,5,5-TRIMETHYLOXAZOLIDINE-2,4-DIONE Upstream-Materialien And Downstream Produkte

Trimethadion Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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