| Identification | Back Directory | [Name]
METHSUXIMIDE | [CAS]
77-41-8 | [Synonyms]
PM 396
Celontin
Petinutin
Mesuximide
Mesuximidum
Methsuximid
Metsuccimide
METHSUXIMIDE
Methsuximide (500 mg)
METHSUXIMIDE USP/EP/BP
Methsuximide (1422001)
alpha-Methylphensuximide
1,3-dimethyl-3-phenylsuccinimide
n,2-dimethyl-2-phenyl-succinimid
N,2-Dimethyl-2-phenylsuccinimide
1,3-dimethyl-3-phenyl-5-pyrrolidinedione
1,3-Dimethyl-3-phenyl-pyrrolidin-2,5-dione
1,3-Dimethyl-3-phenyl-2,5-dioxopyrrolidine
1,3-Dimethyl-3-phenyl-2,5-pyrrolidinedione
1,3-dimethyl-3-phenylpyrrolidine-2,5-dione
1,3-dimethyl-3-phenyl-pyrrolidine-2,5-dione
alpha-methyl-alpha-phenyln-methylsuccinimide
2,5-Pyrrolidinedione, 1,3-dimethyl-3-phenyl-
N-Methyl-alpha,alpha-methylphenylsuccinimide
N-Methyl-alpha-methyl-alpha-phenylsuccinimide
1,3-dimethyl-3-phenyl-pyrrolidine-2,5-quinone
alpha-Methyl-alpha-phenyl N-methyl succinimide | [EINECS(EC#)]
201-026-7 | [Molecular Formula]
C12H13NO2 | [MDL Number]
MFCD00072132 | [MOL File]
77-41-8.mol | [Molecular Weight]
203.24 |
| Chemical Properties | Back Directory | [Melting point ]
52-53° | [Boiling point ]
bp0.1 121-122° | [density ]
1.1255 (rough estimate) | [refractive index ]
1.5440 (estimate) | [storage temp. ]
Refrigerator | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [color ]
White to Off-White | [Water Solubility ]
2.8g/L(25 ºC) |
| Hazard Information | Back Directory | [Description]
Methsuximide is a succinimide that is converted to N-desmethylmethosuximide, a channel blocker that targets low threshold calcium currents. Methsuximide is a substrate of cytochrome P450 (CYP) isoform 2C19 that, in turn, inhibits CYP2C19-mediated metabolism of biguanides. Methsuximide has been shown to have anticonvulsant properties in clinical trials. | [Chemical Properties]
Light Yellow Oil | [Originator]
Celontin,Parke Davis,US,1957 | [Uses]
A calcium channel succinimide antiepileptic drug. Anticonvulsant. | [Definition]
ChEBI: Methsuximide is an organic molecular entity. | [Manufacturing Process]
100 g of α-phenyl-α-methylsuccinic acid and 110 g of 40% aqueous methyl amine are heated together at 200 to 250°C until no more distillate is obtained. Upon vacuum distillation of the residue, the N-methyl-α-phenyl-αmethylsuccinimide, of BP 121° to 122°C at 0.1 mm is obtained. After recrystallization from aqueous ethanol, this compound melts at 52° to 53°C. | [Brand name]
Celontin (Parke-Davis). | [Therapeutic Function]
Anticonvulsant | [Clinical Use]
Although methsuximide is less commonly used, it may be indicated for the control of absence seizures refractory to other drugs.
Although it does not precipitate tonic-clonic convulsions, it often is combined with phenytoin or phenobarbital when absence
seizures coexist with tonic-clonic symptoms. Much of the efficacy of methsuximide is attributed to its desmethyl metabolite. The
half-life of methsuximide is between 2.6 and 4.0 hours, but the half-life for N-desmethylsuximide is 25 hours, causing it to
accumulate substantially. Concentrations of greater than 40 g/mL may be associated with toxicity. Methsuximide is considered
to be more toxic than ethosuximide. | [storage]
Store at -20°C | [References]
[1] nicholls, p. j., and orton, t.c. the physiological disposition of 14c-methsuximide in the rat. br.j.pharmacol. 45(1), 48-59 (1972).
[2] chen g, weston j k, bratton a c. anticonvulsant activity and toxicity of phensuximide, methsuximide and ethosuximide[j]. epilepsia, 1963, 4(1‐4): 66-76.
[3] sigler m, strassburg h m, boenigk h e. effective and safe but forgotten: methsuximide in intractable epilepsies in childhood[j]. seizure, 2001, 10(2): 120-124.
[4] wright j d, helsby n a, ward s a. the role of s‐mephenytoin hydroxylase (cyp2c19) in the metabolism of the antimalarial biguanides[j]. british journal of clinical pharmacology, 1995, 39(4): 441-444.
[5] guengerich f p. human cytochrome p450 enzymes[m]//cytochrome p450. springer us, 1995: 473-535. |
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