Prestwick3_000364

Synopsis, Chemistry

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Also known as: 17692-51-2, Liserdol, Metergolin, Methergoline, Metergolina, Metergolinum

Molecular Formula

C₂₅H₂₉N₃O₂

Molecular Weight

403.5 g/mol

InChI Key

WZHJKEUHNJHDLS-QTGUNEKASA-N

FDA UNII

1501393LY5

A dopamine agonist and serotonin antagonist. It has been used similarly to BROMOCRIPTINE as a dopamine agonist and also for MIGRAINE DISORDERS therapy.

1 2D Structure

Prestwick3_000364

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

benzyl N-[[(6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]methyl]carbamate

2.1.2 InChI

InChI=1S/C25H29N3O2/c1-27-14-18(13-26-25(29)30-16-17-7-4-3-5-8-17)11-21-20-9-6-10-22-24(20)19(12-23(21)27)15-28(22)2/h3-10,15,18,21,23H,11-14,16H2,1-2H3,(H,26,29)/t18-,21+,23+/m0/s1

2.1.3 InChI Key

WZHJKEUHNJHDLS-QTGUNEKASA-N

2.1.4 Canonical SMILES

CN1CC(CC2C1CC3=CN(C4=CC=CC2=C34)C)CNC(=O)OCC5=CC=CC=C5

2.1.5 Isomeric SMILES

CN1C[C@@H](C[C@H]2[C@H]1CC3=CN(C4=CC=CC2=C34)C)CNC(=O)OCC5=CC=CC=C5

2.2 Other Identifiers

2.2.1 UNII

1501393LY5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Liserdol

2. Methergoline

2.3.2 Depositor-Supplied Synonyms

1. 17692-51-2

2. Liserdol

3. Metergolin

4. Methergoline

5. Metergolina

6. Metergolinum

7. C25h29n3o2

8. Fi 6337

9. Fi-6337

10. 1-methyl-n-carbobenzyloxydihydro-d-lysergamin

11. Mls000069437

12. (+)-n-(carboxy)-1-methyl-9,10-dihydrolysergamine Benzyl Ester

13. 1-methyl-8-beta-carbobenzyloxyaminomethyl-10-alpha-ergoline

14. 1,6-dimethyl-8-beta-carbobenzyloxaminomethyl-10-alpha-ergoline

15. D-8-beta-((carbobenzoxyamino)methyl)-1,6-dimethyl-10-alpha-ergoline

16. Smr000059050

17. (((8-beta)-1,6-dimethylergolin-8-yl)methyl)carbamic Acid Phenylmethyl Ester

18. Chembl19215

19. Mce

20. Chebi:64216

21. Metergoline (inn)

22. Nsc-755878

23. Ncgc00017257-09

24. Metergoline [inn]

25. 1501393ly5

26. Dsstox_cid_22584

27. Dsstox_rid_80053

28. Dsstox_gsid_42584

29. Metergoline Phenylmethyl Ester

30. Metergolina [dcit]

31. Metergolinum [latin]

32. Metergolina [spanish]

33. Benzyl {[(8alpha)-1,6-dimethylergolin-8-yl]methyl}carbamate

34. Benzyl {[(8beta)-1,6-dimethylergolin-8-yl]methyl}carbamate

35. Metergoline [inn:ban]

36. Substance 355/255

37. D-8-beta-((carboxyamino)methyl)-1,6-dimethylergoline Benzyl Ester

38. (((8-beta)-1,6-dimethylergolin-8-yl)methyl)carbamic Acid Benzyl Ester

39. Metergolinum [inn-latin]

40. Benzyl N-[[(6ar,9s,10ar)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl]methyl]carbamate

41. Sr-01000000003

42. Ahr 3009

43. Einecs 241-686-3

44. D-n-carbobenzoxydihydro-1-methyllysergamine I

45. Unii-1501393ly5

46. Benzyl 1,6-dimethylergolin-8beta-ylmethylcarbamat

47. Prestwick_657

48. Cas-17692-51-2

49. D-n-carboxydihydro-1-methyllysergamine I Benzyl Ester

50. Metergoline [mi]

51. Opera_id_1642

52. Prestwick0_000364

53. Prestwick1_000364

54. Prestwick2_000364

55. Prestwick3_000364

56. Carbamic Acid, ((1,6-dimethylergolin-8-beta-yl)methyl)-, Benzyl Ester

57. D-8-beta-((carboxyamino)methyl)-1,6-dimethylergoline I Benzyl Ester

58. Biomol-nt_000134

59. Upcmld-dp151

60. Carbamic Acid, (((8beta)-1,6-dimethylergolin-8-yl)methyl)-, Phenylmethyl Ester

61. Metergoline [mart.]

62. Lopac0_000726

63. Bspbio_000487

64. Gtpl133

65. Metergoline [who-dd]

66. Cid_28693

67. Mls001148102

68. Mls002207142

69. Schembl117882

70. Regid_for_cid_28693

71. Spbio_002408

72. Bpbio1_000287

73. Bpbio1_000537

74. N-cbz-[(8beta)-1,6-dimethylergolin-8-yl]methylamine

75. Dtxsid5042584

76. Upcmld-dp151:001

77. Bdbm30704

78. Hms1569i09

79. Hms2096i09

80. Hms2234h19

81. Hms3262a14

82. Hms3411i04

83. Hms3675i04

84. Hms3713i09

85. Lysergamine, N-carboxy-9,10-dihydro-1-methyl-, Benzyl Ester

86. Hy-b1033

87. Zinc3812975

88. Tox21_110808

89. Tox21_500726

90. Stl525769

91. [(8beta)-1,6-dimethylergolin-8-yl)methyl]carbamic Acid Phenylmethyl Ester

92. Akos015889165

93. Carbamic Acid, (((8-beta)-1,6-dimethylergolin-8-yl)methyl)-, Benzyl Ester

94. Tox21_110808_1

95. At31965

96. Ccg-204811

97. Cs-4551

98. Db13520

99. Ks-1369

100. Lp00726

101. Nsc 755878

102. Sdccgsbi-0050704.p002

103. Carbamic Acid, (((8-beta)-1,6-dimethylergolin-8-yl)methyl)-, Phenylmethyl Ester

104. Ncgc00017257-05

105. Ncgc00017257-06

106. Ncgc00017257-07

107. Ncgc00017257-08

108. Ncgc00017257-10

109. Ncgc00017257-11

110. Ncgc00017257-14

111. Ncgc00017257-19

112. Ncgc00022834-04

113. Ncgc00022834-05

114. Ncgc00022834-06

115. Ncgc00022834-07

116. Ncgc00022834-08

117. Ncgc00261411-01

118. B6365

119. Eu-0100726

120. D07218

121. M 3668

122. Sr-01000075561

123. Q6823517

124. Sr-01000000003-2

125. Sr-01000000003-4

126. Sr-01000000003-5

127. Sr-01000000003-6

128. Sr-01000075561-1

129. Brd-k56699285-001-03-7

130. Brd-k56699285-001-18-5

131. [(8?)-1,6-dimethylergolin-8-yl)methyl]carbamic Acid Phenylmethyl Ester

132. [(8beta)-1,6-dimethylergolin-8-yl)methy L]carbamic Acid Phenylmethyl Ester

133. [[(8beta)-1,6-dimethylergolin-8-yl]-methyl]carbamic Acid Phenylmethyl Ester

134. Carbamic Acid, N-[[(8b)-1,6-dimethylergolin-8-yl]methyl]-,phenylmethyl Ester

135. (phenylmethyl) N-[[(6ar,9s,10ar)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl]methyl]carbamate

136. Benzyl (((6ar,9s,10ar)-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl)methyl)carbamate

137. N-[[(6ar,9s,10ar)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl]methyl]carbamic Acid (phenylmethyl) Ester

138. N-[[(6ar,9s,10ar)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl]methyl]carbamic Acid Benzyl Ester

2.4 Create Date

2005-06-29

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₂₉N₃O₂
Molecular Weight	403.5 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	5
Exact Mass	403.22597718 g/mol
Monoisotopic Mass	403.22597718 g/mol
Topological Polar Surface Area	46.5 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	607
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 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Serotonin Antagonists

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS. (See all compounds classified as Serotonin Antagonists.)

Dopamine Agonists

Drugs that bind to and activate dopamine receptors. (See all compounds classified as Dopamine Agonists.)

4.2 ATC Code

G - Genito urinary system and sex hormones

G02 - Other gynecologicals

G02C - Other gynecologicals

G02CB - Prolactine inhibitors

G02CB05 - Metergoline