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Chemistry

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Also known as: 630-93-3, 5,5-diphenylhydantoin sodium salt, Dilantin sodium, Diphenylhydantoin sodium, Diphantoine, Tacosal
Molecular Formula
C15H11N2NaO2
Molecular Weight
274.25  g/mol
InChI Key
FJPYVLNWWICYDW-UHFFFAOYSA-M
FDA UNII
4182431BJH

Phenytoin Sodium
An anticonvulsant that is used to treat a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. The mechanism of therapeutic action is not clear, although several cellular actions have been described including effects on ion channels, active transport, and general membrane stabilization. The mechanism of its muscle relaxant effect appears to involve a reduction in the sensitivity of muscle spindles to stretch. Phenytoin has been proposed for several other therapeutic uses, but its use has been limited by its many adverse effects and interactions with other drugs.
1 2D Structure

Phenytoin Sodium

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;5,5-diphenylimidazolidin-3-ide-2,4-dione
2.1.2 InChI
InChI=1S/C15H12N2O2.Na/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12;/h1-10H,(H2,16,17,18,19);/q;+1/p-1
2.1.3 InChI Key
FJPYVLNWWICYDW-UHFFFAOYSA-M
2.1.4 Canonical SMILES
C1=CC=C(C=C1)C2(C(=O)[N-]C(=O)N2)C3=CC=CC=C3.[Na+]
2.2 Other Identifiers
2.2.1 UNII
4182431BJH
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 5,5-diphenylhydantoin

2. 5,5-diphenylimidazolidine-2,4-dione

3. Antisacer

4. Difenin

5. Dihydan

6. Dilantin

7. Diphenylhydantoin

8. Diphenylhydantoinate, Sodium

9. Epamin

10. Epanutin

11. Fenitoin

12. Hydantol

13. Phenhydan

14. Phenytoin

15. Sodium Diphenylhydantoinate

2.3.2 Depositor-Supplied Synonyms

1. 630-93-3

2. 5,5-diphenylhydantoin Sodium Salt

3. Dilantin Sodium

4. Diphenylhydantoin Sodium

5. Diphantoine

6. Tacosal

7. Antisacer

8. Phenytoin Sodium Salt

9. Diphentoin

10. Epanutin

11. Solantoin

12. Solantyl

13. Eptoin

14. Sodium Phenytoin

15. Diphenylan Sodium

16. Sodium 2,5-dioxo-4,4-diphenylimidazolidin-1-ide

17. Phenytek

18. Sodium Diphenylhydantoin

19. 5,5-diphenylhydantoin Sodium

20. Mls000554076

21. 2,4-imidazolidinedione, 5,5-diphenyl-, Monosodium Salt

22. 4182431bjh

23. Citrullamon

24. Fenidantoin

25. Novodiphenyl

26. Aladdin

27. Alepsin

28. Cumatil

29. Decatona

30. Dihydan

31. Ditomed

32. Enkefal

33. Epdantoin

34. Epileptin

35. Epsolin

36. Eptolin

37. Fenigramon

38. Fenitron

39. Fenytoin

40. Hidantin

41. Phenilep

42. Smr000146393

43. Ditoin

44. Episar

45. Muldis

46. Fenitoin Sodium

47. Hidantal Sodium

48. Lepitoin Sodium

49. Denyl Sodium

50. Aleviatin Sodium

51. Diphenine Sodium

52. Epilantin-e

53. Fenitoina Sodica

54. Soluble Phenytoin

55. Dilantin Infatabs

56. Metinal Idantoina

57. Di-len

58. Dilantin Injection

59. Dilantin Suspension

60. Om-hydantoine Sodium

61. Sdph

62. Prompt Phenytoin Sodium

63. Sodium;5,5-diphenylimidazolidin-3-ide-2,4-dione

64. Mls000028562

65. Sodium Diphenyl Hydantoinate

66. Diphenylhydantoin Sodium Salt

67. Sodium 5,5-diphenylhydantoinate

68. Phenytoin, Sodium Salt

69. Sodium 5,5-diphenyl Hydantoinate

70. Nsc-757274

71. Extended Phenytoin Sodium

72. Smr000058987

73. Einecs 211-148-2

74. Mfcd00069674

75. Hydantoin, 5,5-diphenyl-, Sodium Salt

76. Phenytoin Sodium [usp:jan]

77. Sodium 5,5-diphenylhydantoin

78. Diphenylhydantoin, Sodium Salt

79. Sodium 5,5-diphenyl-2,4-imidazolidinedione

80. Unii-4182431bjh

81. Hydantoin, 5,5-diphenyl-, Monosodium Salt

82. Opera_id_1233

83. Dsstox_cid_3775

84. Dsstox_rid_77190

85. Dsstox_gsid_23775

86. Spectrum1500485

87. Schembl3051683

88. Dtxsid2023775

89. Phenytoin Sodium [vandf]

90. Hms501j09

91. 5,5-diphenylhydatoin Sodium Salt

92. Phenytoin Sodium [mart.]

93. Phenytoin Sodium [usp-rs]

94. Phenytoin Sodium [who-dd]

95. Phenytoin Sodium [who-ip]

96. Hms1920h10

97. Hms2091p14

98. Hms2233k24

99. Hms3259h11

100. Hms3373o11

101. Phenytoin Sodium Salt [mi]

102. Tox21_302338

103. Ccg-39219

104. Akos003273947

105. Akos015951389

106. Akos025310163

107. Phenytoin Sodium [ep Impurity]

108. Phenytoin Sodium [orange Book]

109. Nc00642

110. Nsc 757274

111. Phenytoin Sodium [ep Monograph]

112. 5,5-diphenylhydantoin Sodium Sigmaultra

113. Phenytoin Sodium [usp Monograph]

114. Ncgc00094758-01

115. Ncgc00094758-02

116. Ncgc00164434-01

117. Ncgc00255285-01

118. As-13308

119. Cas-630-93-3

120. 5,5-diphenylhydantoin Sodium Salt, >=99%

121. Phenytoinum Natricum [who-ip Latin]

122. D1331

123. Diphenylhydantoin Sodium [green Book]

124. Phenytoin Sodium For Injection [jan]

125. En300-49847

126. H12023

127. A834211

128. Sr-05000001698

129. Q-201564

130. Sr-05000001698-1

131. Q27258415

132. 2,4-imidazolidinedione, 5,5-diphenyl-, Sodium Salt (1:1)

133. Phenytoin Sodium, European Pharmacopoeia (ep) Reference Standard

134. Phenytoin Sodium, United States Pharmacopeia (usp) Reference Standard

135. Phenytoin Sodium, Pharmaceutical Secondary Standard; Certified Reference Material

2.3.3 Other Synonyms

1. Phenylhydantoin

2.4 Create Date
2005-06-29
3 Chemical and Physical Properties
Molecular Weight 274.25 g/mol
Molecular Formula C15H11N2NaO2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass274.07182188 g/mol
Monoisotopic Mass274.07182188 g/mol
Topological Polar Surface Area47.2 Ų
Heavy Atom Count20
Formal Charge0
Complexity356
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NamePhenytoin sodium
Drug LabelPhenytoin sodium is an antiepileptic drug. Phenytoin sodium is related to the barbiturates in chemical structure, but has a five-membered ring. The chemical name is sodium 5,5-diphenyl-2, 4-imidazolidinedione, having the following structural formula:...
Active IngredientPhenytoin sodium
Dosage FormInjectable
RouteInjection
Strength50mg/ml
Market StatusPrescription
CompanyHospira; Hikma Maple; X-gen Pharms; Luitpold

2 of 2  
Drug NamePhenytoin sodium
Drug LabelPhenytoin sodium is an antiepileptic drug. Phenytoin sodium is related to the barbiturates in chemical structure, but has a five-membered ring. The chemical name is sodium 5,5-diphenyl-2, 4-imidazolidinedione, having the following structural formula:...
Active IngredientPhenytoin sodium
Dosage FormInjectable
RouteInjection
Strength50mg/ml
Market StatusPrescription
CompanyHospira; Hikma Maple; X-gen Pharms; Luitpold

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)


Cytochrome P-450 CYP1A2 Inducers

Drugs and compounds that induce the synthesis of CYTOCHROME P-450 CYP1A2. (See all compounds classified as Cytochrome P-450 CYP1A2 Inducers.)


Voltage-Gated Sodium Channel Blockers

A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS. (See all compounds classified as Voltage-Gated Sodium Channel Blockers.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Cytochrome P450 1A2 Inducers [MoA]; Cytochrome P450 2B6 Inducers [MoA]; Cytochrome P450 2C19 Inducers [MoA]; Cytochrome P450 2C8 Inducers [MoA]; Cytochrome P450 2C9 Inducers [MoA]; Cytochrome P450 2D6 Inducers [MoA]; Cytochrome P450 3A Inducers [MoA]; Decreased Central Nervous System Disorganized Electrical Activity [PE]; Anti-epileptic Agent [EPC]

API Reference Price

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