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2,5-Pyrrolidinedione, 1-methyl-3-phenyl-, (3R)-

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Synopsis

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Chemistry

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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

Phensuximide

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 Formula	C₁₁H₁₁NO₂
Molecular Weight	189.21 g/mol
XLogP3	0.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	189.078978594 g/mol
Monoisotopic Mass	189.078978594 g/mol
Topological Polar Surface Area	37.4 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	256
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

FDF Dossiers