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| METHSUXIMIDE Basic information |
| Product Name: | METHSUXIMIDE | | Synonyms: | 1,3-dimethyl-3-phenyl-pyrrolidine-2,5-dione;1,3-dimethyl-3-phenylpyrrolidine-2,5-dione;1,3-dimethyl-3-phenyl-pyrrolidine-2,5-quinone;Methsuximide (500 mg);1,3-Dimethyl-3-phenyl-2,5-dioxopyrrolidine;1,3-Dimethyl-3-phenyl-2,5-pyrrolidinedione;1,3-dimethyl-3-phenyl-5-pyrrolidinedione;1,3-Dimethyl-3-phenyl-pyrrolidin-2,5-dione | | CAS: | 77-41-8 | | MF: | C12H13NO2 | | MW: | 203.24 | | EINECS: | 201-026-7 | | Product Categories: | Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;CELONTIN | | Mol File: | 77-41-8.mol |
| METHSUXIMIDE Chemical Properties |
| 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) |
| METHSUXIMIDE Usage And Synthesis |
| 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. | | 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. | | 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. |
| METHSUXIMIDE Preparation Products And Raw materials |
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