5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidindion

Bezeichnung:5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidindion

CAS-Nr50-12-4

Englisch Name:(S)-MEPHENYTOIN

CBNumberCB0225135

SummenformelC12H14N2O2

Molgewicht218.25

MOL-Datei50-12-4.mol

Synonyma

Mephenytoin

5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidindion

5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidindion physikalisch-chemischer Eigenschaften

Schmelzpunkt	135-138 °C
Siedepunkt	358.94°C (rough estimate)
Dichte	1.154±0.06 g/cm3 (20 ºC 760 Torr)
Brechungsindex	1.6660 (estimate)
storage temp.	2-8°C
Löslichkeit	DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
Aggregatzustand	solid
pka	pKa 8.1 (Uncertain)
Farbe	off-white
CAS Datenbank	50-12-4(CAS DataBase Reference)
EPA chemische Informationen	Mephenytoin (50-12-4)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38
S-Sätze:	26-36
WGK Germany	2
HS Code	2933210000
Giftige Stoffe Daten	50-12-4(Hazardous Substances Data)
Toxizität	LD50 i.p. in mice: 300 mg/kg (Dzhagatspanyan)

Gefahreninformationscode (GHS)

(S)-MEPHENYTOIN Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Mephenytoin 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.
Originator
Mesantoin,Sandoz
Verwenden
rac-Mephenytoin is an anticonvulsant agent.
Verwenden
Anticonvulsant.
Definition
ChEBI: Mephenytoin is an imidazolidine-2,4-dione (hydantoin) in which the imidazolidine nucleus carries a methyl group at N-3 and has ethyl and phenyl substituents at C-5. An anticonvulsant, it is no longer available in the USA or the UK but is still studied largely because of its interesting hydroxylation polymorphism. It has a role as an anticonvulsant.
Manufacturing Process
23 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.
Trademarks
Mesantoin (Novartis).
Therapeutic Function
Anticonvulsant, Antiepileptic
Biologische Aktivität
CYP2C19 substrate. Anticonvulsant.
Biochem/physiol Actions
CYP2B6 and CYP2C19 substrate; anticonvulsive, antiepileptic.
Nebenwirkungen
Side effects, including rash, fever, and fatal blood dyscrasia, prevent the use as an anticonvulsant drug of first choice.
Sicherheitsprofil
Poison 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 Upstream-Materialien And Downstream Produkte

5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidindion Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

50-12-4, (S)-MEPHENYTOIN Verwandte Suche:

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