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3A,16A-Apovincaminic Acid Ethyl Ester

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5 USP
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Vinpocetine

Synopsis

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Chemistry

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Also known as: 42971-09-5, Cavinton, Ceractin, Apovincaminic acid ethyl ester, Bravinton, Ethyl apovincamin-22-oate

Molecular Formula

C₂₂H₂₆N₂O₂

Molecular Weight

350.5 g/mol

InChI Key

DDNCQMVWWZOMLN-IRLDBZIGSA-N

FDA UNII

543512OBTC

Vinpocetine has been investigated for the treatment of Epilepsy.

1 2D Structure

Vinpocetine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

ethyl (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate

2.1.2 InChI

InChI=1S/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m1/s1

2.1.3 InChI Key

DDNCQMVWWZOMLN-IRLDBZIGSA-N

2.1.4 Canonical SMILES

CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC

2.1.5 Isomeric SMILES

CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC

2.2 Other Identifiers

2.2.1 UNII

543512OBTC

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cavinton

2. Ethyl Apovincaminate

3. Ethyl Apovincaminate Tartrate (1:1)

4. Ethyl Apovincaminate, (+-)-isomer

5. Ethyl Apovincaminate, (16alpha)-isomer

6. Ethyl Apovincaminate, (3alpha,16alpha)-isomer

7. Ethyl Apovincaminate, 2-oxopentanedioate (1:1)

8. Ethyl Apovincaminate, 3h-labeled

9. Kavinton

10. Rgh-4405

11. Tcv-3b

2.3.2 Depositor-Supplied Synonyms

1. 42971-09-5

2. Cavinton

3. Ceractin

4. Apovincaminic Acid Ethyl Ester

5. Bravinton

6. Ethyl Apovincamin-22-oate

7. Ultra-vinca

8. Tcv-3b

9. Rgh 4405

10. Ethyl (+)-apovincaminate

11. Vinporal

12. Cis-apovincaminic Acid Ethyl Ester

13. Rgh-4405

14. Ethyl (+)-cis-apovincaminate

15. Tcv 3b

16. (+)-apovincaminic Acid Ethyl Ester

17. Ethyl Apovincaminate

18. (+)-cis-apovincaminic Acid Ethyl Ester

19. Ay 27,255

20. 3-alpha,16-alpha-apovincaminic Acid Ethyl Ester

21. Nsc-760093

22. Chembl71752

23. Ay-27,255

24. Mls000069635

25. 543512obtc

26. (41s,13as)-ethyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1h-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate

27. Ncgc00018204-09

28. Vinpocetinum

29. Ay-27255

30. Smr000058241

31. Eburnamenine-14-carboxylic Acid, Ethyl Ester, (3alpha,16alpha)-

32. Dsstox_cid_3740

33. Dsstox_rid_77176

34. Dsstox_gsid_23740

35. Ethyl (41s,13as)-13a-ethyl-2,3,41,5,6,13a-hexahydro-1h-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate

36. Vinpocetinum [inn-latin]

37. Eburnamenine-14-carboxylic Acid, Ethyl Ester, (3a,16a)-

38. Apovincaminate D'ethyle

39. Apovincaminate D'ethyle [french]

40. Ethyl (15s,19s)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate

41. Eburnamenine-14-carboxylic Acid Ethyl Ester

42. Sr-01000075633

43. Einecs 256-028-0

44. Brn 0900803

45. Vinpocetin

46. Unii-543512obtc

47. Vinpocetine (jan/usan/inn)

48. Vinpocetine-ethyl Apovincaminate

49. 3a,16a-apovincaminic Acid Ethyl Ester

50. Ncgc00016854-03

51. Vinpocetine [usan:inn:ban:jan]

52. Prestwick_963

53. Vinpocetin- Bio-x

54. Cas-42971-09-5

55. Mfcd00211233

56. Spectrum_001400

57. Vinpocetine (cavinton)

58. Ay 27255

59. Specplus_000327

60. Vinpocetine [mi]

61. Opera_id_1325

62. Prestwick0_000268

63. Prestwick1_000268

64. Prestwick2_000268

65. Prestwick3_000268

66. Spectrum2_001529

67. Spectrum3_000961

68. Spectrum4_001075

69. Spectrum5_000966

70. Vinpocetine [dsc]

71. Vinpocetine [inn]

72. Vinpocetine [jan]

73. Vinpocetine [usan]

74. V 6383

75. Vinpocetine [vandf]

76. Vinpocetine [mart.]

77. Lopac0_001257

78. Schembl50081

79. Bspbio_000116

80. Bspbio_002561

81. Kbiogr_001430

82. Kbioss_001880

83. Vinpocetine [usp-rs]

84. Vinpocetine [who-dd]

85. Mls001076294

86. Divk1c_006423

87. Spectrum1503115

88. Vinpocetine, >=98%, Solid

89. Ethyl (3alpha,16alpha)-eburnamenine-14-carboxylate

90. Spbio_001318

91. Spbio_002335

92. Bpbio1_000128

93. Cid_443955

94. Gtpl5285

95. Vinpocetine, Analytical Standard

96. Dtxsid5023740

97. Regid_for_cid_443955

98. Chebi:32297

99. Kbio1_001367

100. Kbio2_001880

101. Kbio2_004448

102. Kbio2_007016

103. Kbio3_001781

104. Hms1568f18

105. Hms1922g05

106. Hms2090j22

107. Hms2092l06

108. Hms2095f18

109. Hms3263l16

110. Hms3402d12

111. Hms3411h11

112. Hms3675h11

113. Hms3712f18

114. Hms3887e17

115. Pharmakon1600-01503115

116. Vinpocetine [ep Monograph]

117. (3alpha, 16alpha)-eburnamenine-14-carboxylic Acid Ethyl Ester

118. 68780-77-8

119. Amy39087

120. Bcp04123

121. Tox21_110648

122. Tox21_110839

123. Tox21_501257

124. Bdbm50059033

125. Ccg-39307

126. Eburnamenine-14-carboxylic Acid, Ethyl Ester, (3-alpha,16-alpha)-

127. Nsc760093

128. Pd-185

129. S2110

130. Zinc19796031

131. Akos015896480

132. Tox21_110648_1

133. Cs-0545

134. Db12131

135. Lp01257

136. Nsc 760093

137. Sdccgsbi-0051224.p003

138. Vinpocetine 1.0 Mg/ml In Acetonitrile

139. (3s,16s)-apovincaminic Acid Ethylester

140. Ncgc00018204-05

141. Ncgc00018204-06

142. Ncgc00018204-07

143. Ncgc00018204-08

144. Ncgc00018204-10

145. Ncgc00018204-11

146. Ncgc00018204-13

147. Ncgc00021727-04

148. Ncgc00021727-05

149. Ncgc00021727-06

150. Ncgc00021727-07

151. Ncgc00168782-01

152. Ncgc00261942-01

153. Ncgc00263865-01

154. Ncgc00263865-04

155. Ac-22612

156. As-13868

157. Bv164528

158. Hy-13295

159. Eburnamenine-14-carboxylic Acid Ethyl Ester;

160. Eu-0101257

161. V0115

162. D01371

163. Ab00052317_02

164. 971v095

165. Q420288

166. Sr-01000000118

167. Sr-01000000118-3

168. Sr-01000075633-1

169. Sr-01000075633-3

170. Sr-01000075633-4

171. W-202748

172. Brd-k53318339-001-05-8

173. (3?,16?)-eburnamenine-14-carboxylic Acid Ethyl Ester

174. Vinpocetine, European Pharmacopoeia (ep) Reference Standard

175. Vinpocetine, United States Pharmacopeia (usp) Reference Standard

176. Eburnamenine 14-carboxylic Acid Ethyl Ester (3.alpha.,16.alpha.)

177. (11as,11bs)-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1h-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic Acid Ethyl Ester

178. (3as,11bs)-3a-ethyl-1,2,3,3a,10,11b-hexahydro-11h-5a,11a-diaza-benzo[cd]fluoranthene-5-carboxylic Acid Ethyl Ester

179. (41s,13as)-ethyl13a-ethyl-2,3,41,5,6,13a-hexahydro-1h-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate

180. 115986-87-3

181. 11a-ethyl-2,3,4,5,11a,11b-hexahydro-1h-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic Acid 2-nitrooxy-ethyl Ester(vinpocetine)

182. Ethyl (15s,19s)-15-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2(7),3,5,8(18),16-pentaene-17-carboxylate

183. Ethyl (15s,19s)-15-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₆N₂O₂
Molecular Weight	350.5 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	350.199428076 g/mol
Monoisotopic Mass	350.199428076 g/mol
Topological Polar Surface Area	34.5 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	617
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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

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.)

Phosphodiesterase Inhibitors

Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases. (See all compounds classified as Phosphodiesterase Inhibitors.)

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

Nootropic Agents

Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. (See all compounds classified as Nootropic Agents.)

4.2 ATC Code

N - Nervous system

N06 - Psychoanaleptics

N06B - Psychostimulants, agents used for adhd and nootropics

N06BX - Other psychostimulants and nootropics

N06BX18 - Vinpocetine

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API Reference Price

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