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(S)-MEPHENYTOIN

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(S)-MEPHENYTOIN Basic information
(S)-MEPHENYTOIN Chemical Properties
  • Melting point:135-138 °C
  • Boiling point:358.94°C (rough estimate)
  • Density 1.154±0.06 g/cm3 (20 ºC 760 Torr)
  • refractive index 1.6660 (estimate)
  • storage temp. 2-8°C
  • form solid
  • pkapKa 8.1 (Uncertain)
  • color off-white
  • CAS DataBase Reference50-12-4(CAS DataBase Reference)
  • EPA Substance Registry SystemMephenytoin (50-12-4)
Safety Information
MSDS
(S)-MEPHENYTOIN Usage And Synthesis
  • DescriptionMephenytoin is N-methylated at position 3 with an ethyl group replacing one of the phenyl substituents at position 5. It is indicated for focal and jacksonian seizures in patients refractory to less toxic AEDs. Mephenytoin produces more sedation than phenytoin and should be used only when safer drugs have failed, because it is associated with an increased incidence of serious toxicities, such as severe rash, agranulocytosis, and hepatitis. Its N-desmethyl metabolite, 5-phenyl- 5-ethylhydantoin, contributes to both efficacy and toxicity for mephenytoin. The drug is no longer commercially available inside but is still available outside the United States.
  • OriginatorMesantoin,Sandoz
  • UsesAnticonvulsant.
  • Usesrac-Mephenytoin is an anticonvulsant agent.
  • Manufacturing Process23 parts sodium was dissolved in 300 parts of ethanol and added to 160 parts of 5-phenylcyanacetamide in 750 parts of ethanol. A mixture was cooled straight away and a sodium salt of amide precipitated as a white powder. 200 parts of ethyl iodide was added to this mixture and heated for 1.5 hours. The ethanol was distilled off, water was added to the residue and rapidly hardened oil precipitated. After recrystallization from ethanol, 5-ethyl-5- phenylacetamide afforded; MP: 116°C.
    100 parts of sodium hydroxide was solved in 500 parts of water and added to 83 parts of bromine by cooling. 5-Ethyl-5-phenylacetamide was added to above prepared mixture. It dissolved quickly, whereupon all mass was heated some time, cooled and stood at room temperature some hours. Then a solution of sodium bisulfite was added before the formed precipitate dissolved. The reaction mixture was filtered, the filtrate was acidified to give rapidly hardened oil. After recrystallization from ethanol 5-ethyl-3-methyl-5-phenylhydantoin was yielded as the bright needles; MP: 201°-202°C.
  • brand nameMesantoin (Novartis).
  • Therapeutic FunctionAnticonvulsant, Antiepileptic
  • Biological ActivityCYP2C19 substrate. Anticonvulsant.
  • Safety ProfilePoison by ingestion and intraperitoneal routes. Human systemic effects by ingestion: somnolence, hemorrhage, changes in teeth and supporting structures. Human mutation data reported. An experimental teratogen. An FDA proprietary drug used as an anticonvulsant. When heated to decomposition it emits toxic fumes of NOx.
(S)-MEPHENYTOIN Preparation Products And Raw materials
(S)-MEPHENYTOIN(50-12-4)Related Product Information
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  • Company Name:3B Pharmachem (Wuhan) International Co.,Ltd.
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