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

• ChemBase ID: 4407
• Molecular Formular: C12H13NO2
• Molecular Mass: 203.23712
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-dimethyl-3-phenylpyrrolidine-2,5-dione
• IUPAC Traditional name: mesuximide; methsuximide
• Brand Name: Petinutin; Celontin
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.027071
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.463009
• LogD (pH = 7.4): 1.463009
• Log P: 1.463009
• Molar Refractivity: 56.3486 cm^3
• Polarizability: 21.926273 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.46
• LOG S: -1.98
• Solubility (Water): 2.13e+00 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light Yellow Oil
• Melting Point: 48-52°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

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.

REFERENCES

• 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)