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ChemicalBook--->CAS DataBase List--->50-12-4

50-12-4

50-12-4 Structure

50-12-4 Structure
IdentificationMore
[Name]

(S)-MEPHENYTOIN
[CAS]

50-12-4
[Synonyms]

(+/-)-5-ETHYL-3-METHYL-5-PHENYL-2,4-IMIDAZOLIDINEDIONE
(+/-)-5-ETHYL-3-METHYL-5-PHENYLHYDANTOIN
(+/-)-MEPHENYTOIN
MEPHENYTOIN
(S)-(+)-5-ETHYL-3-METHYL-5-PHENYL-2,4-IMIDAZOLIDINEDIONE
(S)-(+)-5-ETHYL-3-METHYL-5-PHENYLHYDANTOIN
(S)-5-ETHYL-3-METHYL-5-PHENYLHYDANTOIN
(S)-(+)-MEPHENYTOIN
(S)-MEPHENYTOIN
2,4-Imidazolidinedione, 5-ethyl-3-methyl-5-phenyl-
3-Ethylnirvanol
3-Methyl-5,5-ethylphenylhydantoin
3-Methyl-5,5-phenylethylhydantoin
3-Methyl-5-ethyl-5-phenylhydantoin
5-Ethyl-3-methyl-5-phenyl-2,4(3H,5H)-imidazoledione
5-ethyl-3-methyl-5-phenyl-4-imidazolidinedione
5-ethyl-3-methyl-5-phenyl-hydantoi
5-Ethyl-3-methyl-5-phenylimidazolidin-2,4-dione
5-Ethyl-5-fenyl-3-methylhydantoin
Epiazin
[EINECS(EC#)]

200-012-8
[Molecular Formula]

C12H14N2O2
[MDL Number]

MFCD00270025
[Molecular Weight]

218.25
[MOL File]

50-12-4.mol
Chemical PropertiesBack Directory
[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
[solubility ]

DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
[form ]

solid
[pka]

pKa 8.1 (Uncertain)
[color ]

off-white
[CAS DataBase Reference]

50-12-4(CAS DataBase Reference)
[EPA Substance Registry System]

Mephenytoin (50-12-4)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

2
[HS Code ]

2933210000
[Safety Profile]

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.
[Hazardous Substances Data]

50-12-4(Hazardous Substances Data)
[Toxicity]

LD50 i.p. in mice: 300 mg/kg (Dzhagatspanyan)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

POTASSIUM CYANIDE-->Ammonium carbonate-->Propiophenone-->Cyanide, Quant Test Strips-->Sodium bisulfite-->Sodium-->MEPHOBARBITAL-->1-(1-cyano-1-phenylpropyl)-3-methylurea-->2,4-Imidazolidinedione, 5-ethyl-5-phenyl-, (+-)--->Methylamine-->Methylurea-->Iodomethane-->N,N-Dimethylformamide dimethyl acetal
Hazard InformationBack Directory
[Description]

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
[Uses]

Anticonvulsant.
[Uses]

rac-Mephenytoin is an anticonvulsant agent.
[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.
[Brand name]

Mesantoin (Novartis).
[Therapeutic Function]

Anticonvulsant, Antiepileptic
[Biological Activity]

CYP2C19 substrate. Anticonvulsant.
[Biochem/physiol Actions]

CYP2B6 and CYP2C19 substrate; anticonvulsive, antiepileptic.
[Side effects]

Side effects, including rash, fever, and fatal blood dyscrasia, prevent the use as an anticonvulsant drug of first choice.
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

50-12-4(sigmaaldrich)
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