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2D Structure
Also known as: 86-34-0, Succitimal, Milontin, Lifene, Epimid, 1-methyl-3-phenylpyrrolidine-2,5-dione
Molecular Formula
C11H11NO2
Molecular Weight
189.21  g/mol
InChI Key
WLWFNJKHKGIJNW-UHFFFAOYSA-N
FDA UNII
6WVL9C355G

Phensuximide is a member of the succinimide class with anticonvulsant properties. 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.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-methyl-3-phenylpyrrolidine-2,5-dione
2.1.2 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
2.1.3 InChI Key
WLWFNJKHKGIJNW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN1C(=O)CC(C1=O)C2=CC=CC=C2
2.2 Other Identifiers
2.2.1 UNII
6WVL9C355G
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Phensuccimide

2. Phensuximide, (+-)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 86-34-0

2. Succitimal

3. Milontin

4. Lifene

5. Epimid

6. 1-methyl-3-phenylpyrrolidine-2,5-dione

7. Phensuximid

8. Phenylsuximide

9. Milonton

10. Mirontin

11. 1-methyl-3-phenyl-2,5-pyrrolidinedione

12. Phensuximidum

13. Succinimide, N-methyl-2-phenyl-

14. Racemic Phensuximide

15. N-methyl-2-phenylsuccinimide

16. 1-methyl-3-phenylsuccinimide

17. Pm 334

18. 1-methyl-3-phenylpyrrolidin-2,5-dione

19. Ai3-20372

20. 2,5-pyrrolidinedione, 1-methyl-3-phenyl-

21. Nsc-760079

22. 6wvl9c355g

23. Chebi:8079

24. Phensuccimide

25. Fenosuccimide

26. N-methyl-.alpha.-phenylsuccinimide

27. Epimid; Lifene; Milontin; Milonton

28. Pm-334

29. Fensuccimide

30. Methylphenylsuccinimide

31. Fensuccimide [dcit]

32. Dsstox_cid_3460

33. Dsstox_rid_77035

34. Dsstox_gsid_23460

35. Fensuximida [inn-spanish]

36. Phensuximidum [inn-latin]

37. Fensuximida

38. N-methyl-alpha-phenylsuccinimide

39. Rs-phensuximide

40. Milontin (tn)

41. (+-)-n-methyl-2-phenylsuccinimide

42. Einecs 201-664-6

43. Brn 0155329

44. Unii-6wvl9c355g

45. Lifen

46. Phensuximide [usp:inn:ban]

47. Cas-86-34-0

48. Ncgc00016339-01

49. (+/-)-n-methyl-2-phenylsuccinimide

50. Prestwick0_001061

51. Prestwick1_001061

52. Prestwick2_001061

53. Prestwick3_001061

54. Phensuximide (usp/inn)

55. Phensuximide [mi]

56. Phensuximide [inn]

57. Chembl797

58. Phensuximide [vandf]

59. Schembl35333

60. Bspbio_001042

61. Phensuximide [mart.]

62. 5-21-11-00188 (beilstein Handbook Reference)

63. Mls002154134

64. (+/-)-phensuximide

65. N-methyl-2-phenyl-succinimide

66. Phensuximide [usp-rs]

67. Phensuximide [who-dd]

68. 2,5-pyrrolidinedione, 1-methyl-3-phenyl-, (+-)-

69. Spbio_002961

70. Bpbio1_001148

71. Gtpl7612

72. Dtxsid4023460

73. Hms1571e04

74. Hms2098e04

75. Hms2235h10

76. Hms3264e08

77. Hms3369l21

78. Hms3715e04

79. Hms3887e05

80. Pharmakon1600-01505458

81. Phensuximide [orange Book]

82. Phensuximide [usp Impurity]

83. Hy-b1730

84. N-methyl-3-phenylsuccinimide

85. Tox21_110382

86. Ac7001

87. Mfcd00072136

88. Nsc760079

89. Akos006230701

90. Tox21_110382_1

91. Ccg-213454

92. Db00832

93. Nsc 760079

94. (.+/-.)-n-methyl-2-phenylsuccinimide

95. N-methyl-3-phenylpyrrolidinedione

96. Ncgc00179333-01

97. Ncgc00179333-03

98. Ac-15962

99. Ai320372

100. Smr001233441

101. Sy251116

102. 1-methyl-3-phenyl-2,5-pyrrolidinedione #

103. Ai3 20372

104. Ab00514025

105. Cs-0013738

106. C07437

107. D00508

108. Ab00514025_07

109. 086p340

110. Q999805

111. Sr-01000842158

112. Sr-01000842158-2

113. Brd-a18043272-001-03-2

114. 2,5-pyrrolidinedione, 1-methyl-3-phenyl-, (+/-)-

115. 34367-67-4

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 189.21 g/mol
Molecular Formula C11H11NO2
XLogP30.8
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass189.078978594 g/mol
Monoisotopic Mass189.078978594 g/mol
Topological Polar Surface Area37.4 Ų
Heavy Atom Count14
Formal Charge0
Complexity256
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For the treatment of epilepsy.


5 Pharmacology and Biochemistry
5.1 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.


5.2 ATC Code

N - Nervous system

N03 - Antiepileptics

N03A - Antiepileptics

N03AD - Succinimide derivatives

N03AD02 - Phensuximide


5.3 Absorption, Distribution and Excretion

Absorption

Rapid and complete.


5.4 Metabolism/Metabolites

Hepatic.


5.5 Mechanism of Action

Phensuximide's mechanism of action not understood, but may act in inhibitory neuronal systems that are important in the generation of the three per second rhythm. It's effects may be related to its ability to inhibit depolarization-induced accumulation of cyclic AMP and cyclic GMP in brain tissue.