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

• ChemBase ID: 711
• Molecular Formular: C11H11NO2
• Molecular Mass: 189.21054
• Monoisotopic Mass: 189.0789786
• SMILES: O=C1N(C(=O)CC1c1ccccc1)C
• Canonical SMILES: CN1C(=O)CC(C1=O)c1ccccc1
• InChI: InChI=1S/C11H11NO2/c1-12-10(13)7-9(11(12)14)8-5-3-2-4-6-8/h2-6,9H,7H2,1H3
• InChIKey: WLWFNJKHKGIJNW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-3-phenylpyrrolidine-2,5-dione
• IUPAC Traditional name: N-methyl-2-phenyl succinimide; phensuximide
• Brand Name: (+/-)-N-Methyl-2-phenylsuccinimide; 1-Methyl-3-Phenylsuccinimide; Epimid; Fenosuccimide; Fensuccimide [DCIT]; Fensuximida [INN-Spanish]; Lifene; Methylphenylsuccinimide; Milontin; Milontin (TN); Milonton; Mirontin; Mirotin; 7 Phenosuccimide; N-Methyl-2-phenylsuccinimide; N-Methyl-alpha-phenolsuccinimide; N-Methyl-alpha-phenylsuccinimide; Phensuximid; Phensuximide (USP); Phensuximide [BAN:INN]; Phensuximidum [INN-Latin]; Phenylsuximide; Succinimide, N-methyl-2-phenyl-; Succitimal
• Synonyms: Phensuximide

Database IDs

• CAS Number: 86-34-0
• PubChem SID: 46505695; 160964174
• PubChem CID: 6839
• ATC CODE: N03AD02
• CHEMBL: 797
• Chemspider ID: 6578
• DrugBank ID: DB00832
• KEGG ID: D00508
• Unique Ingredient Identifier: 6WVL9C355G
• Wikipedia Title: Phensuximide
• Medline Plus: a682237

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.403624
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.90699476
• LogD (pH = 7.4): 0.90699476
• Log P: 0.90699476
• Molar Refractivity: 51.8476 cm^3
• Polarizability: 20.0874 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.61
• LOG S: -1.93
• Solubility (Water): 2.21e+00 g/l

PROPERTIES

Physical Property

• Solubility: 7020 mg/L
• Hydrophobicity(logP): 0.7

Pharmacology Properties

• Protein Bound: 21%

DETAILS

DrugBank - DB00832

• Drug Groups: approved
• Description: Phensuximide is an anticonvulsant in the succinimide class. It suppresses the paroxysmal three cycle per second spike and wave EEG pattern associated with lapses of consciousness in petit mal seizures. The frequency of attacks is reduced by depression of nerve transmission in the motor cortex.
• Indication: For the treatment of epilepsy.
• Pharmacology: Phensuximide suppresses the paroxysmal three cycle per second spike and wave EEG pattern associated with lapses of consciousness in absence (petit mal) seizures. The frequency of attacks is reduced by depression of nerve transmission in the motor cortex.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Rapid and complete.
• Protein Binding: 21%
• References: Rankin GO, Cressey-Veneziano K, Wang RT, Brown PI: Urinary tract effects of phensuximide in the Sprague-Dawley and Fischer 344 rat. J Appl Toxicol. 1986 Oct;6(5):349-56. [Pubmed] ; CHEN G, WESTON JK, BRATTON AC Jr: Anticonvulsant activity and toxicity of phensuximide, methsuximide and ethosuximide. Epilepsia. 1963 Mar;4:66-76. [Pubmed] ; Ferrendelli JA, Kinscherf DA: Inhibitory effects of anticonvulsant drugs on cyclic nucleotide accumulation in brain. Ann Neurol. 1979 Jun;5(6):533-8. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Rankin GO, Cressey-Veneziano K, Wang RT, Brown PI: Urinary tract effects of phensuximide in the Sprague-Dawley and Fischer 344 rat. J Appl Toxicol. 1986 Oct;6(5):349-56. Pubmed
• CHEN G, WESTON JK, BRATTON AC Jr: Anticonvulsant activity and toxicity of phensuximide, methsuximide and ethosuximide. Epilepsia. 1963 Mar;4:66-76. Pubmed
• Ferrendelli JA, Kinscherf DA: Inhibitory effects of anticonvulsant drugs on cyclic nucleotide accumulation in brain. Ann Neurol. 1979 Jun;5(6):533-8. Pubmed