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Prestwick3_000147

Prestwick3_000147

Synopsis, Chemistry

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Also known as: 27848-84-6, Nimergoline, Ergobel, Nicergolinum, Nicotergoline, Sermion

Molecular Formula

C₂₄H₂₆BrN₃O₃

Molecular Weight

484.4 g/mol

InChI Key

YSEXMKHXIOCEJA-FVFQAYNVSA-N

FDA UNII

JCV8365FWN

An ergot derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. It may ameliorate cognitive deficits in CEREBROVASCULAR DISORDERS.

1 2D Structure

Prestwick3_000147

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(6aR,9R,10aS)-10a-methoxy-4,7-dimethyl-6a,8,9,10-tetrahydro-6H-indolo[4,3-fg]quinolin-9-yl]methyl 5-bromopyridine-3-carboxylate

2.1.2 InChI

InChI=1S/C24H26BrN3O3/c1-27-13-17-8-21-24(30-3,19-5-4-6-20(27)22(17)19)9-15(12-28(21)2)14-31-23(29)16-7-18(25)11-26-10-16/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3/t15-,21-,24+/m1/s1

2.1.3 InChI Key

YSEXMKHXIOCEJA-FVFQAYNVSA-N

2.1.4 Canonical SMILES

CN1CC(CC2(C1CC3=CN(C4=CC=CC2=C34)C)OC)COC(=O)C5=CC(=CN=C5)Br

2.1.5 Isomeric SMILES

CN1C[C@@H](C[C@]2([C@H]1CC3=CN(C4=CC=CC2=C34)C)OC)COC(=O)C5=CC(=CN=C5)Br

2.2 Other Identifiers

2.2.1 UNII

JCV8365FWN

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Circo Maren

2. Circo-maren

3. Ergobel

4. F.i. 6714

5. Fisifax

6. Nicergobeta

7. Nicergolin Atid

8. Nicergolin Lindo

9. Nicergolin Neuraxpharm

10. Nicergolin Ratiopharm

11. Nicergolin Teva

12. Nicergolin Von Ct

13. Nicergolin-neuraxpharm

14. Nicergolin-ratiopharm

15. Nicergolin-teva

16. Nicerium

17. Nicotergoline

18. Nimergoline

19. Sermion

20. Von Ct, Nicergolin

2.3.2 Depositor-Supplied Synonyms

1. 27848-84-6

2. Nimergoline

3. Ergobel

4. Nicergolinum

5. Nicotergoline

6. Sermion

7. Cergodum

8. Duracebrol

9. Nicergolent

10. Vasospan

11. Circo-maren

12. Nimergoline Base

13. Dilasenil

14. Ergotop

15. Nilogrin

16. Memoq

17. Sermion (tn)

18. 10-methoxy-1,6-dimethylergoline-8beta-methanol 5-bromonicotinate

19. Jcv8365fwn

20. Chebi:31902

21. Nicergolin [german]

22. Nicergolina [dcit]

23. Nsc-150531

24. ((6ar,9r,10as)-10a-methoxy-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl)methyl 5-bromonicotinate

25. Fi-6714

26. Rp 19651

27. Ncgc00017259-04

28. Nicergolinum [inn-latin]

29. Nicergolina

30. Nicergolin

31. Dsstox_cid_25607

32. Dsstox_rid_81000

33. Dsstox_gsid_45607

34. [(2s,4r,7r)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate

35. [(6ar,9r,10as)-10a-methoxy-4,7-dimethyl-6a,8,9,10-tetrahydro-6h-indolo[4,3-fg]quinoline-9-yl]methyl 5-bromopyridine-3-carboxylate

36. Cas-27848-84-6

37. Fi 6714

38. Sr-01000597616

39. Einecs 248-694-6

40. Unii-jcv8365fwn

41. Nsc 150531

42. Brn 4828393

43. 1-methyl-lumilysergol 8-(5-bromonicotinate) 10-methyl Ether

44. Nicergoline,(s)

45. (+)-10-methoxy-1,6-dimethylergoline-8-beta-methanol 5-bromonicotinate

46. 10-methoxy-1,6-dimethylergoline-8beta-methanol 5-bromonicotinate (ester)

47. Nicergoline [usan:inn:ban:jan]

48. 10-methoxy-1,6-dimethyl-ergolin-8-beta-methanol-(5-bromnicotinat) [german]

49. 8-beta-((5-bromonicotinoyloxy)methyl)-1,6-dimethyl-10-alpha-methoxyergoline

50. Nicergoline- Bio-x

51. Mfcd00869626

52. 10-methoxy-1,6-dimethylergoline-8-methanol 5-bromo-3-pyrindinecarboxylate (ester)

53. Ergoline-8-beta-methanol, 10-methoxy-1,6-dimethyl-, 5-bromo-3-pyridinecarboxylate (ester)

54. Spectrum_001370

55. Nicergoline [mi]

56. 10-methoxy-1,6-dimethyl-ergolin-8-beta-methanol-(5-bromnicotinat)

57. Prestwick0_000147

58. Prestwick1_000147

59. Prestwick2_000147

60. Prestwick3_000147

61. Spectrum2_001414

62. Spectrum3_001933

63. Spectrum4_000440

64. Spectrum5_001352

65. Nicergoline [inn]

66. Nicergoline [jan]

67. 5-bromonicotinic Acid 10-methoxy-1,6-dimethylergoline-8-methyl Ester

68. Nicergoline [usan]

69. Ergoline-8-beta-methanol, 10-methoxy-1,6-dimethyl-, 5-bromonicotinate (ester)

70. Ergoline-8beta-methanol, 10-methoxy-1,6-dimethyl-, 5-bromonicotinate (ester)

71. Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-, (8beta)-, 5-bromo-3-pyridinecarboxylate (ester)

72. Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-, 5-bromo-3-pyridinecarboxylate (ester), (8beta)-

73. Nicergoline [mart.]

74. Schembl22964

75. Bspbio_000254

76. Bspbio_003533

77. Kbiogr_000800

78. Kbioss_001850

79. Nicergoline [who-dd]

80. Divk1c_000124

81. Spectrum1501133

82. Spbio_001488

83. Spbio_002193

84. Bpbio1_000280

85. Chembl1372950

86. Dtxsid7045607

87. Hms500g06

88. Kbio1_000124

89. Kbio2_001850

90. Kbio2_004418

91. Kbio2_006986

92. Kbio3_002787

93. Nicergoline (jp17/usan/inn)

94. Nicergoline For System Suitability

95. Ninds_000124

96. Hms1568m16

97. Hms1923o09

98. Hms2089i03

99. Hms2092f07

100. Hms2095m16

101. Hms3712m16

102. Hms3886c03

103. Nicergoline [ep Monograph]

104. Nicergoline For Peak Identification

105. Pharmakon1600-01501133

106. 4-oxazolecarboxylicacid, 5-methyl-

107. Ex-a4135

108. Hy-b0702

109. Zinc3873817

110. Tox21_110810

111. Ccg-39032

112. Nsc757853

113. S4797

114. Akos005067888

115. Akos015969107

116. Tox21_110810_1

117. Db00699

118. Nicergoline 1.0 Mg/ml In Acetonitrile

119. Nsc-757853

120. Idi1_000124

121. Qtl1_000060

122. Ncgc00017259-03

123. Ncgc00017259-05

124. Ncgc00017259-07

125. Ncgc00024678-02

126. Ncgc00024678-03

127. As-12239

128. Bn166697

129. Sbi-0051652.p002

130. N0904

131. D01290

132. T72213

133. Ab00052214-04

134. Ab00052214_05

135. 848n846

136. A853601

137. Sr-05000001751

138. J-016896

139. Nicergoline, Analytical Standard, For Drug Analysis

140. Q2623398

141. Sr-01000597616-1

142. Sr-01000597616-2

143. Sr-05000001751-1

144. Brd-k76810206-001-05-7

145. Brd-k76810206-001-06-5

146. Nicergoline, European Pharmacopoeia (ep) Reference Standard

147. (8beta)-10-methoxy-1,6-dimethylergoline-8-methanol 5-bromo-3-pyridinecarboxylate (ester)

148. [(8r,10s)-10-methoxy-1,6-dimethylergolin-8-yl]methyl 5-bromopyridine-3-carboxylate

149. 10-methoxy-1,6-dimethylergoline-8.beta.-methanol 5-bromonicotinate (ester)

150. Nicergoline For Peak Identification, European Pharmacopoeia (ep) Reference Standard

151. Nicergoline For System Suitability, European Pharmacopoeia (ep) Reference Standard

152. ((6ar,9r,10as)-10a-methoxy-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl)methyl5-bromonicotinate

153. [(6ar,9r,10as)-10a-methoxy-4,7-dimethyl-6a,8,9,10-tetrahydro-6h-indolo[4,3-fg]quinolin-9-yl]methyl 5-bromopyridine-3-carboxylate

154. 5-bromopyridine-3-carboxylic Acid [(8r,10s)-10-methoxy-1,6-dimethylergolin-8-yl]methyl Ester

155. Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-, (8.beta.)-, 5-bromo-3-pyridinecarboxylate (ester)

156. Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-,5-bromo-3-pyridinecarboxylate (ester), (8b)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₂₆BrN₃O₃
Molecular Weight	484.4 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	483.11575 g/mol
Monoisotopic Mass	483.11575 g/mol
Topological Polar Surface Area	56.6 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	681
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
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 senile dementia, migraines of vascular origin, transient ischemia, platelet hyper-aggregability, and macular degeneration.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Nicergoline is a potent vasodilator (improves brain blood flow). On the cerebral level it prompts a lowering of vascular resistance, an increase in arterial flow and stimulates the use of oxygen and glucose. Nicergoline also improves blood circulation in the lungs and limbs and has been shown to inhibit blood platelet aggregation.

5.2 MeSH Pharmacological Classification

Adrenergic alpha-Antagonists

Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma. (See all compounds classified as Adrenergic alpha-Antagonists.)

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.)

Vasodilator Agents

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

5.3 ATC Code

C - Cardiovascular system

C04 - Peripheral vasodilators

C04A - Peripheral vasodilators

C04AE - Ergot alkaloids

C04AE02 - Nicergoline

5.4 Mechanism of Action

Nicergoline acts by inhibiting the postsynaptic alpha(1)-adrenoceptors on vascular smooth muscle. This inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation. Therefore the mechanism of Nicergoline is to increase vascular circulation in the brain, thereby enhancing the transmission of nerve signals across the nerve fibres, which secrete acetylcholine as a neural transmitter.