1,3-dimethyl-3-phenylpyrrolidine-2,5-dione

• ChemBase编号: 4407
• 分子式: C12H13NO2
• 平均质量: 203.23712
• 单一同位素质量: 203.09462866
• SMILES: O=C1N(C(=O)CC1(c1ccccc1)C)C
• Canonical SMILES: CN1C(=O)CC(C1=O)(C)c1ccccc1
• InChI: InChI=1S/C12H13NO2/c1-12(9-6-4-3-5-7-9)8-10(14)13(2)11(12)15/h3-7H,8H2,1-2H3
• InChIKey: AJXPJJZHWIXJCJ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,3-dimethyl-3-phenylpyrrolidine-2,5-dione
• IUPAC传统名: mesuximide; methsuximide
• 商标名: Petinutin; Celontin
• 别名: Metsuccimide; N,2-Dimethyl-2-phenylsuccinimide; N-methyl-alpha-methyl-alpha-phenylsuccinimide; Alpha-methylphensuximide; Alpha-methyl-alpha-phenyl n-methyl succinimide; 1,3-Dimethyl-3-phenylsuccinimide; 1,3-Dimethyl-3-phenyl-pyrrolidin-2,5-dione; 1,3-Dimethyl-3-phenyl-2,5-pyrrolidinedione; 1,3-Dimethyl-3-phenyl-2,5-dioxopyrrolidine; (RS)-1,3-Dimethyl-3-phenyl-2,5-pyrrolidindion; Methsuximide; Mesuximide; Mesuximidum [inn-latin]; Mesuximida [inn-spanish]; Methsuximid; Metosuccimmide [DCIT]; (+/-)-Mesuximide; Celontin; Mesuximidum; PM 396

登记号

• CAS号: 77-41-8
• PubChem SID: 46505339; 160967839
• PubChem CID: 6476

理论计算性质

JChem

• Acid pKa: 19.027071
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.463009
• LogD (pH = 7.4): 1.463009
• Log P: 1.463009
• 摩尔折射率: 56.3486 cm^3
• 极化性: 21.926273 Å^3
• 极化表面积: 37.38 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.46
• LOG S: -1.98
• 溶解度: 2.13e+00 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: Light Yellow Oil
• 熔点: 48-52°C

安全信息

• 保存条件: Refrigerator

详细说明

DrugBank - DB05246

• Drug Groups: approved
• Description: Mesuximide (or methsuximide) is an anticonvulsant medication. It is sold by Pfizer under the name Petinutin. [Wikipedia]
• Indication: For the control of absence (petit mal) seizures that are refractory to other drugs.
• Pharmacology: Used in the treatment of epilepsy. Methsuximide suppresses the paroxysmal three cycle per second spike and wave activity associated with lapses of consciousness which is common in absence (petit mal) seizures. The frequency of epileptiform attacks is reduced, apparently by depression of the motor cortex and elevation of the threshold of the central nervous system to convulsive stimuli.
• Toxicity: Acute overdoses may produce nausea, vomiting, and CNS depression including coma with respiratory depression. Levels greater than 40 µg/mL have caused toxicity and coma has been seen at levels of 150 µg/mL.
• Affected Organisms: Humans and other mammals
• Half Life: 1.4-2.6 hours for mesuximide and 28-38 hours for the active metabolite.
• References: Hurst DL: Methsuximide therapy of juvenile myoclonic epilepsy. Seizure. 1996 Mar;5(1):47-50. [Pubmed] ; Besag FM, Berry DJ, Pool F: Methsuximide lowers lamotrigine blood levels: A pharmacokinetic antiepileptic drug interaction. Epilepsia. 2000 May;41(5):624-7. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - M271900

A calcium channel succinimide antiepileptic drug. Anticonvulsant.

参考文献

• Besag FM, Berry DJ, Pool F: Methsuximide lowers lamotrigine blood levels: A pharmacokinetic antiepileptic drug interaction. Epilepsia. 2000 May;41(5):624-7. Pubmed
• Hurst DL: Methsuximide therapy of juvenile myoclonic epilepsy. Seizure. 1996 Mar;5(1):47-50. Pubmed
• Marshall, P.G., et al.: J. Pharm. Pharmacol., 6, 740 (1954)
• Bialer, M., et al.: Epilepsy Res., 51, 31 (1954)
• Merlot, C., et al.: Drug Discov. Today, 8, 594 (1954)
• Bajaj, S., et al.: Bioorg. Med. Chem., 13, 3263 (1954)