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Neostigmine Bromide

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Chemistry

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Also known as: 114-80-7, Eustigmin bromide, Neoserine bromide, Vagostigmin, Kirkstigmine bromide, Syntostigmin bromide

Molecular Formula

C₁₂H₁₉BrN₂O₂

Molecular Weight

303.20 g/mol

InChI Key

LULNWZDBKTWDGK-UHFFFAOYSA-M

FDA UNII

005SYP50G5

A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike PHYSOSTIGMINE, does not cross the blood-brain barrier.

1 2D Structure

Neostigmine Bromide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium;bromide

2.1.2 InChI

InChI=1S/C12H19N2O2.BrH/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;/h6-9H,1-5H3;1H/q+1;/p-1

2.1.3 InChI Key

LULNWZDBKTWDGK-UHFFFAOYSA-M

2.1.4 Canonical SMILES

CN(C)C(=O)OC1=CC=CC(=C1)[N+](C)(C)C.[Br-]

2.2 Other Identifiers

2.2.1 UNII

005SYP50G5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bromide, Neostigmine

2. Methylsulfate, Neostigmine

3. Neostigmine

4. Neostigmine Methylsulfate

5. Polstigmine

6. Proserine

7. Prostigmin

8. Prostigmine

9. Prozerin

10. Synstigmin

11. Syntostigmine

2.3.2 Depositor-Supplied Synonyms

1. 114-80-7

2. Eustigmin Bromide

3. Neoserine Bromide

4. Vagostigmin

5. Kirkstigmine Bromide

6. Syntostigmin Bromide

7. Neo-proserin

8. 3-((dimethylcarbamoyl)oxy)-n,n,n-trimethylbenzenaminium Bromide

9. Proserine Bromide

10. Stigmanol Bromide

11. Synstigmin Bromide

12. Leostigmine Bromide

13. Neostigmini Bromidum

14. Philostigmin Bromide

15. Prostigmin

16. Neo Proserine

17. Neostigmine Methyl Bromide

18. Bromure De Neostigmine

19. Bromuro De Neostigmina

20. Neostigmine (bromide)

21. Neoproserine

22. Neostigminebromide

23. (m-hydroxyphenyl)trimethylammonium Bromide Dimethylcarbamate

24. 3-[(dimethylcarbamoyl)oxy]-n,n,n-trimethylanilinium Bromide

25. Nsc-757233

26. 3-dimethylcarbamoxyphenyl Trimethyl Ammonium Bromide

27. 114-80-7 (bromide)

28. Mls000028387

29. [3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium;bromide

30. 3-hydroxyphenyltrimethylammonium Bromide Dimethylcarbamic Ester

31. Chebi:179557

32. 005syp50g5

33. Eustigmin Bromide;neoserine Bromide

34. Smr000058591

35. Stigmosan Bromide

36. Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-n,n,n-trimethyl-, Bromide

37. Prostigmin Bromide

38. Dsstox_cid_21075

39. Dsstox_rid_79621

40. Prostigmine Bromide

41. Dsstox_gsid_41075

42. Synstigmini Bromidum

43. Vagostigmine Bromide

44. Syntostigmine Bromide

45. 3-(dimethylcarbamoyloxy)trimethylanilinium Ion Bromatum

46. Synthostigmine Bromide

47. Syntostigmin (tablet)

48. Synstigminbromid

49. Benzenaminium, 3-[[(dimethylamino)carbonyl]oxy]-n,n,n-trimethyl-, Bromide

50. Neostigmina Bromuro

51. Neostigmina Bromuro [dcit]

52. Neostigmini Bromidum [inn-latin]

53. Sr-01000000073

54. Ncgc00163240-01

55. Cas-114-80-7

56. Einecs 204-054-8

57. Bromure De Neostigmine [inn-french]

58. Bromuro De Neostigmina [inn-spanish]

59. Unii-005syp50g5

60. Vagostigmin (tn)

61. Prestwick_352

62. Mfcd00011795

63. Neostigmine Bromide [usp:inn:ban:jan]

64. Opera_id_1504

65. Carbamic Acid, Dimethyl-, Ester With (m-hydroxyphenyl)trimethylammonium Bromide

66. Neo Proserine [jan]

67. Schembl41128

68. Mls001146913

69. Chembl54126

70. Spectrum1500428

71. Lczc2572

72. Dtxsid9041075

73. Neostigmine Bromide (prostigmin)

74. Neostigmine Bromide [mi]

75. Hms500i07

76. Neostigmine Bromide [inn]

77. Neostigmine Bromide [jan]

78. Hms1569m18

79. Hms1920p15

80. Hms2091h18

81. Hms2096m18

82. Hms2235j11

83. Hms3262d13

84. Hms3372e02

85. Hms3713m18

86. Pharmakon1600-01500428

87. Neostigmine Bromide [vandf]

88. 3-(n,n-dimethylcarbamoyloxy)-n,n,n,-trimethylanilinium Bromide

89. Act05638

90. Hy-b0423

91. Neostigmine Bromide [mart.]

92. Neostigmine Bromide (jan/usp/inn)

93. Tox21_112037

94. Tox21_500816

95. Ccg-39110

96. Neostigmine Bromide [usp-rs]

97. Neostigmine Bromide [who-dd]

98. Neostigmine Bromide [who-ip]

99. Nsc757233

100. S2490

101. Akos015895725

102. Ammonium, (m-hydroxyphenyl)trimethyl-, Bromide, Dimethylcarbamate

103. Tox21_112037_1

104. Lp00816

105. Nsc 757233

106. Ncgc00015730-11

107. Ncgc00094149-01

108. Ncgc00094149-02

109. Ncgc00094149-03

110. Ncgc00094149-04

111. Ncgc00261501-01

112. Bs-14646

113. Neostigmine Bromide [ep Monograph]

114. Mls-0002855.p042

115. Neostigmine Bromide [usp Monograph]

116. Neostigmini Bromidum [who-ip Latin]

117. Eu-0100816

118. Ft-0651572

119. N0358

120. C08197

121. C71473

122. D00995

123. N 2001

124. A803245

125. Sr-01000000073-3

126. Sr-01000000073-5

127. Sr-01000000073-7

128. W-108598

129. (3-dimethylcarbamoyloxyphenyl)trimethylammonium Bromide

130. Q27105147

131. Neostigmine Bromide, >=98% (hplc And Titration), Powder

132. (3-hydroxyphenyl)trimethylammonium Bromide Dimethyl Carbamate

133. [3-[dimethylamino(oxo)methoxy]phenyl]-trimethylammonium Bromide

134. Neostigmine Bromide, European Pharmacopoeia (ep) Reference Standard

135. Neostigmine Bromide, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₉BrN₂O₂
Molecular Weight	303.20 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	302.06299 g/mol
Monoisotopic Mass	302.06299 g/mol
Topological Polar Surface Area	29.5 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	246
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	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Cholinesterase Inhibitors

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)

Parasympathomimetics

Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here. (See all compounds classified as Parasympathomimetics.)

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