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Bromocriptine Mesylate

Bromocriptine Mesylate

Synopsis, Chemistry

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Also known as: 22260-51-1, Parlodel, Bromocriptine mesilate, Bromocryptine mesylate, Pravidel, Bromocriptine methanesulfonate

Molecular Formula

C₃₃H₄₄BrN₅O₈S

Molecular Weight

750.7 g/mol

InChI Key

NOJMTMIRQRDZMT-GSPXQYRGSA-N

FDA UNII

FFP983J3OD

A semisynthetic ergotamine alkaloid that is a dopamine D2 agonist. It suppresses prolactin secretion.

1 2D Structure

Bromocriptine Mesylate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6aR,9R)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;methanesulfonic acid

2.1.2 InChI

InChI=1S/C32H40BrN5O5.CH4O3S/c1-16(2)12-24-29(40)37-11-7-10-25(37)32(42)38(24)30(41)31(43-32,17(3)4)35-28(39)18-13-20-19-8-6-9-22-26(19)21(27(33)34-22)14-23(20)36(5)15-18;1-5(2,3)4/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39);1H3,(H,2,3,4)/t18-,23-,24+,25+,31-,32+;/m1./s1

2.1.3 InChI Key

NOJMTMIRQRDZMT-GSPXQYRGSA-N

2.1.4 Canonical SMILES

CC(C)CC1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CN(C5CC6=C(NC7=CC=CC(=C67)C5=C4)Br)C)O.CS(=O)(=O)O

2.1.5 Isomeric SMILES

CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@H]4CN([C@@H]5CC6=C(NC7=CC=CC(=C67)C5=C4)Br)C)O.CS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

FFP983J3OD

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2 Bromo Alpha Ergocryptine

2. 2 Bromo Alpha Ergokryptine

3. 2 Bromoergocryptine

4. 2 Bromoergocryptine Mesylate

5. 2 Bromoergocryptine Methanesulfonate

6. 2 Bromoergokryptine

7. 2-bromo-alpha-ergocryptine

8. 2-bromo-alpha-ergokryptine

9. 2-bromoergocryptine

10. 2-bromoergocryptine Mesylate

11. 2-bromoergocryptine Methanesulfonate

12. 2-bromoergokryptine

13. Bromocriptin

14. Bromocriptine

15. Bromocryptin

16. Cb 154

17. Cb-154

18. Cb154

19. Mesylate, 2-bromoergocryptine

20. Mesylate, Bromocriptine

21. Methanesulfonate, 2-bromoergocryptine

22. Parlodel

2.3.2 Depositor-Supplied Synonyms

1. 22260-51-1

2. Parlodel

3. Bromocriptine Mesilate

4. Bromocryptine Mesylate

5. Pravidel

6. Bromocriptine Methanesulfonate

7. Cycloset

8. Bagren

9. Cb-154 Mesylate

10. Bromergon

11. (+)-bromocriptine Methanesulfonate

12. 2-bromo-alpha-ergocryptine Mesylate

13. Cb-154

14. Cb-154 Mesilate

15. Cb 154

16. 2-bromoergocryptine Monomethanesulfonate (salt)

17. Ffp983j3od

18. Bromocriptine (mesylate)

19. Chebi:3182

20. 2-bromoergocryptine Mesylate

21. Nsc-755915

22. Oline-9-carboxamide Methanesulfonate

23. Bromocryptine Methanesulfonate

24. (5'a)-2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trione Mesylate

25. Bromocriptine Mesylate [usan]

26. Nsc169774

27. Sr-01000597796

28. Einecs 244-881-1

29. Unii-ffp983j3od

30. 2-bromo-alpha-ergocryptine Methanesulfonate

31. Sr-01000075356

32. 2-bromine-alpha-ergocryptine Methanesulfonate

33. 2-bromo-alpha-ergokryptine-mesilate [german]

34. Bromocriptine Mesylate [usan:usp]

35. Parlodel (tn)

36. (5'alpha)-2-bromo-12'-hydroxy-5'-(2-methylpropyl)-3',6',18-trioxo-2'-(propan-2-yl)ergotaman Methanesulfonate (salt)

37. (6ar,9r)-5-bromo-n-[(2r,5s,10as,10bs)-10b-hydroxy-2-(1-methylethyl)-5-(2-methylpropyl)-3,6-dioxooctahydro-8h-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quin

38. 2-bromo-alpha-ergokryptine-mesilate

39. Prestwick_771

40. Cas-22260-51-1

41. Dsstox_cid_197

42. Bromocriptinemesylate

43. Alpha-ergocryptine, 2-bromo-, Methanesulfonate

44. Dsstox_rid_75426

45. Dsstox_gsid_20197

46. Schembl40559

47. 2-bromo-12'-hydroxy-5'alpha-isobutyl-2'-isopropylergotaman-3',6',18-trione Monomethanesulphonate

48. Bromocriptine Mesylate (usp)

49. Bromocriptine Mesylate- Bio-x

50. Bromocriptine Mesilate (jp17)

51. Chembl1200503

52. Dtxsid6020197

53. 2-bromo ?-ergocryptine Mesylate

54. Cb 154 Methanesulfonate (salt)

55. C32h40brn5o5.ch3so3h

56. Hms1568i04

57. Hms3260d03

58. Hms3411k09

59. Hms3675k09

60. Hms3712i04

61. 2-bromo Alpha-ergocryptine Mesylate

62. Bromocriptine Mesilate [jan]

63. Tox21_303597

64. Tox21_500171

65. Hy-12705a

66. Bromocriptine Mesylate [vandf]

67. .alpha.-ergocryptine, Methanesulfonate

68. Akos015896276

69. Bromocriptine Mesilate [mart.]

70. Bromocriptine Mesilate [who-dd]

71. Bromocriptine Mesylate [usp-rs]

72. Ccg-220121

73. Ccg-221475

74. Cs-6048

75. Lp00171

76. Nsc 755915

77. Nsc-169774

78. Ncgc00257268-01

79. Ncgc00260856-01

80. Bb164266

81. Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, Monomethanesulfonate (salt), (5'alpha)-

82. Bromocriptine Methanesulfonate [mi]

83. Bromocriptine Mesylate [orange Book]

84. 2-bromo-a-ergocryptine Methanesulfonate Salt

85. B6298

86. Bromocriptine Mesilate [ep Monograph]

87. Eu-0100171

88. Bromocriptine Mesylate [usp Monograph]

89. B 2134

90. D00780

91. D81822

92. 2-bromo-.alpha.-ergocryptine Monomethanesulfonate

93. A903911

94. Sr-01000075356-1

95. Sr-01000597796-1

96. Sr-01000597796-2

97. Q27105974

98. 2-bromoergocryptine Monomethanesulphonate (salt)

99. (+)-2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6'-18-trione Methanesulfonate Salt

100. (5'alpha)-2-bromo-12'-hydroxy-5'-(2-methylpropyl)-2'-(propan-2-yl)-3',6',18-trioxoergotaman Methanesulfonate

101. (5'alpha)-2-bromo-12'-hydroxy-5'-isobutyl-2'-isopropyl-3',6',18-trioxoergotaman Methanesulfonate

102. (6ar,9r)-5-bromo-n-[(1s,2s,4r,7s)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide;methanesulfonic Acid

103. Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5.alpha.)-, Methanesulfonate (1:1)

104. Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, Monomethanesulfonate (salt), (5'.alpha.)-

105. Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, Monomethanesulphonate (salt), (5'.alpha.)-

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₃₃H₄₄BrN₅O₈S
Molecular Weight	750.7 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	5
Exact Mass	749.20940 g/mol
Monoisotopic Mass	749.20940 g/mol
Topological Polar Surface Area	181 Å²
Heavy Atom Count	48
Formal Charge	0
Complexity	1320
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	Bromocriptine mesylate
Drug Label	Bromocriptine mesylate is an ergot derivative with potent dopamine receptor agonist activity. Each bromocriptine mesylate tablet, USP for oral administration contains 2.5 mg bromocriptine (as the mesylate). Bromocriptine mesylate is chemically design...
Active Ingredient	Bromocriptine mesylate
Dosage Form	Tablet; Capsule
Route	Oral
Strength	eq 5mg base; eq 2.5mg base
Market Status	Prescription
Company	Lek Pharms; Paddock; Zydus Pharms Usa; Mylan

2 of 6
Drug Name	Cycloset
PubMed Health	Bromocriptine (By mouth)
Drug Classes	Antidiabetic, Antiparkinsonian, Prolactin Secretion Inhibitor
Drug Label	CYCLOSET Tablets contain bromocriptine mesylate, a dopamine receptor agonist. Bromocriptine mesylate is chemically designated [Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, monomethanesulf
Active Ingredient	Bromocriptine mesylate
Dosage Form	Tablet
Route	Oral
Strength	eq 0.8mg base
Market Status	Prescription
Company	Veroscience

3 of 6
Drug Name	Parlodel
PubMed Health	Bromocriptine (By mouth)
Drug Classes	Antidiabetic, Antiparkinsonian, Prolactin Secretion Inhibitor
Drug Label	Parlodel (bromocriptine mesylate) is an ergot derivative with potent dopamine receptor agonist activity. Each Parlodel (bromocriptine mesylate) SnapTabs tablet for oral administration contains 2 mg and each capsule contains 5 mg bromocriptine...
Active Ingredient	Bromocriptine mesylate
Dosage Form	Tablet; Capsule
Route	Oral
Strength	eq 5mg base; eq 2.5mg base
Market Status	Prescription
Company	Us Pharms Holdings I

4 of 6
Drug Name	Bromocriptine mesylate
Drug Label	Bromocriptine mesylate is an ergot derivative with potent dopamine receptor agonist activity. Each bromocriptine mesylate tablet, USP for oral administration contains 2.5 mg bromocriptine (as the mesylate). Bromocriptine mesylate is chemically design...
Active Ingredient	Bromocriptine mesylate
Dosage Form	Tablet; Capsule
Route	Oral
Strength	eq 5mg base; eq 2.5mg base
Market Status	Prescription
Company	Lek Pharms; Paddock; Zydus Pharms Usa; Mylan

5 of 6
Drug Name	Cycloset
PubMed Health	Bromocriptine (By mouth)
Drug Classes	Antidiabetic, Antiparkinsonian, Prolactin Secretion Inhibitor
Drug Label	CYCLOSET Tablets contain bromocriptine mesylate, a dopamine receptor agonist. Bromocriptine mesylate is chemically designated [Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, monomethanesulf
Active Ingredient	Bromocriptine mesylate
Dosage Form	Tablet
Route	Oral
Strength	eq 0.8mg base
Market Status	Prescription
Company	Veroscience

6 of 6
Drug Name	Parlodel
PubMed Health	Bromocriptine (By mouth)
Drug Classes	Antidiabetic, Antiparkinsonian, Prolactin Secretion Inhibitor
Drug Label	Parlodel (bromocriptine mesylate) is an ergot derivative with potent dopamine receptor agonist activity. Each Parlodel (bromocriptine mesylate) SnapTabs tablet for oral administration contains 2 mg and each capsule contains 5 mg bromocriptine...
Active Ingredient	Bromocriptine mesylate
Dosage Form	Tablet; Capsule
Route	Oral
Strength	eq 5mg base; eq 2.5mg base
Market Status	Prescription
Company	Us Pharms Holdings I

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antiparkinson Agents

Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists. (See all compounds classified as Antiparkinson Agents.)

Hormone Antagonists

Chemical substances which inhibit the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. (See all compounds classified as Hormone Antagonists.)

Dopamine Agonists

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

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Ergot Derivative [EPC]; Ergolines [CS]