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Ebselen

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11 Drugs in Development

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Chemistry

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Also known as: 60940-34-3, 2-phenyl-1,2-benzisoselenazol-3(2h)-one, 2-phenylbenzo[d][1,2]selenazol-3(2h)-one, Ebselenum, 2-phenyl-1,2-benzoselenazol-3-one, Spi-1005

Molecular Formula

C₁₃H₉NOSe

Molecular Weight

274.19 g/mol

InChI Key

DYEFUKCXAQOFHX-UHFFFAOYSA-N

FDA UNII

40X2P7DPGH

Ebselen is a organoselenium compound with anti-inflammatory, anti-oxidant and cytoprotective activity. Ebselen acts as a glutathione peroxidase mimetic and is thereby able to prevent cellular damage induced by reactive oxygen species (ROS). In addition, this agent inhibits the activity of a variety of enzymes including nitric oxide synthase (NOS), 5-lipoxygenase, cyclooxygenase, protein kinase C (PKC), NADPH oxidase and gastric H+/K+-ATPase. Furthermore, ebselen may be neuroprotective due to its ability to neutralize free radicals upon NMDA receptor activation thus, reducing lipoperoxidation mediated by glutamate-induced excitotoxicity.

1 2D Structure

Ebselen

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-phenyl-1,2-benzoselenazol-3-one

2.1.2 InChI

InChI=1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H

2.1.3 InChI Key

DYEFUKCXAQOFHX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C3[Se]2

2.2 Other Identifiers

2.2.1 UNII

40X2P7DPGH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-phenyl-1,2-benzoisoselenazol-3(2h)-one

2. 2-phenylbenzoisoselenazol-3(2h)-one

3. Dr 3305

4. Dr-3305

5. Dr3305

6. Pz 51

7. Pz-51

8. Rp 60931

9. Spi 1005

10. Spi-1005

11. Spi1005

2.3.2 Depositor-Supplied Synonyms

1. 60940-34-3

2. 2-phenyl-1,2-benzisoselenazol-3(2h)-one

3. 2-phenylbenzo[d][1,2]selenazol-3(2h)-one

4. Ebselenum

5. 2-phenyl-1,2-benzoselenazol-3-one

6. Spi-1005

7. Ebselene

8. Ebseleno

9. Ebselen [inn]

10. Ebselene [french]

11. Ebselenum [latin]

12. Harmokisane

13. Ebseleno [spanish]

14. Pz 51

15. Dr-3305

16. Pz-51

17. Pz51

18. Mls000028488

19. Dr3305

20. Ccris 3714

21. 1,2-benzisoselenazol-3(2h)-one, 2-phenyl-

22. 2-phenyl-1,2-benzisoselenazolin-3-one

23. Smr000058445

24. Unii-40x2p7dpgh

25. 2-phenyl-1,2-benzoisoselenazol-3(2h)-one

26. Chembl51085

27. Nsc 639762

28. Prestwick_1057

29. Spi-3005

30. Prestwick0_000740

31. Prestwick1_000740

32. Prestwick2_000740

33. Prestwick3_000740

34. Spectrum2_001441

35. Spectrum3_000799

36. Spectrum4_000445

37. Spectrum5_001713

38. Lopac-e-3520

39. Mfcd00210937

40. Nsc639762

41. Nsc-639762

42. Nsc-757883

43. 40x2p7dpgh

44. Lopac0_000541

45. Ncgc00015412-06

46. Bspbio_000700

47. Bspbio_001342

48. Bspbio_002538

49. Cpd000058445

50. Kbiogr_000062

51. Kbiogr_000830

52. Kbioss_000062

53. Divk1c_000951

54. Spbio_001301

55. Spbio_002639

56. Cas-60940-34-3

57. Mls001148646

58. Bpbio1_000770

59. Bcbcmap01_000149

60. Chebi:77543

61. Hms502p13

62. Kbio1_000951

63. Kbio2_000062

64. Kbio2_002630

65. Kbio2_005198

66. Kbio3_000123

67. Kbio3_000124

68. Kbio3_001758

69. Ninds_000951

70. E 3520

71. Bio2_000062

72. Bio2_000542

73. Hms1361d04

74. Hms1570c22

75. Hms1791d04

76. Hms1989d04

77. Hms2052n09

78. Ccg-39161

79. Ac-1124

80. C13h9nose

81. Idi1_000951

82. Idi1_033812

83. Qtl1_000035

84. Ncgc00015412-01

85. Ncgc00015412-02

86. Ncgc00015412-03

87. Ncgc00015412-13

88. Ncgc00024072-03

89. Ncgc00024072-04

90. Ncgc00024072-05

91. Ncgc00178610-01

92. Ncgc00178610-02

93. Ncgc00178610-03

94. Ab00053217

95. Eu-0100541

96. Mls-0003066.0001

97. Brd-k29359156-001-06-1

98. Dr 3305

99. Rp 60931

100. Sr-01000003081

101. Ac1l1fdw

102. Cid3194

103. Spi1005

104. Ebselen (c5)

105. Nchembio.109-comp1

106. 2-phenyl-1,2-benzoselenazol-3(2h)-one

107. Ls-33527

108. Sam001247071

109. Ebselen [jan]

110. Ebselen [mi]

111. Ebselen [mart.]

112. Opera_id_1643

113. Ebselen [who-dd]

114. Ebselen, Cysteine Modifier

115. Cid_3194

116. Dsstox_cid_25150

117. Dsstox_rid_80704

118. C042986

119. Dsstox_gsid_45150

120. Schembl33829

121. Mls001424261

122. Mls006010108

123. E3520_sigma

124. I09-1611

125. Dtxsid7045150

126. Bdbm34233

127. Gtpl10583

128. Hms2097c22

129. Hms2235a11

130. Hms3394n09

131. Hms3402d04

132. Hms3649o05

133. Hms3714c22

134. Hms3873n13

135. Kuc112559n

136. Pharmakon1600-01501188

137. Bcp17134

138. Ex-a1447

139. Spi-1005;pz-51

140. Tox21_110140

141. 2-phenyl-benzo[d]isoselenazol-3-one

142. Dap001372

143. Nsc757883

144. S6676

145. Akos015898841

146. Cs-5534

147. Db12610

148. Lp00541

149. Nc00431

150. Sdccgsbi-0050524.p004

151. Ksc-325-014

152. Ncgc00015412-04

153. Ncgc00015412-05

154. Ncgc00015412-07

155. Ncgc00015412-08

156. Ncgc00015412-09

157. Ncgc00015412-10

158. Ncgc00015412-11

159. Ncgc00015412-12

160. Ncgc00015412-21

161. Phenyl-1,2-benzisoselenazol-3(2h)-one

162. 2-phenyl-1,2-benzisoselazol-3(2h)-one

163. Hy-13750

164. Sy052687

165. Sbi-0050524.p003

166. 2-phenyl-1,2-benzisoselenazole-3(2h)-one

167. Db-072873

168. 2-phenyl-1,2-benzoisoselenazole-3(2h)-one

169. E0946

170. Ft-0759332

171. 2-phenyl-1,2-benzoisoselenazole-3-(2h)-one

172. 2-phenyl-benzo[d]isoselenazol-3-one(ebselen)

173. C75847

174. Ab00053217_25

175. 940e343

176. A868855

177. Q5332073

178. Sr-01000003081-2

179. Sr-01000003081-7

180. Sr-01000003081-8

181. Brd-k29359156-001-23-6

182. Sr-01000003081-10

183. Sr-01000003081-14

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₉NOSe
Molecular Weight	274.19 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Exact Mass	274.98494 g/mol
Monoisotopic Mass	274.98494 g/mol
Topological Polar Surface Area	20.3 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	275
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Anti-Ulcer Agents

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

Cyclooxygenase Inhibitors

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)

Neuroprotective Agents

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)

Drugs in Development