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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

Bromocriptine Mesylate
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 Weight 750.7 g/mol
Molecular Formula C33H44BrN5O8S
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count5
Exact Mass749.20940 g/mol
Monoisotopic Mass749.20940 g/mol
Topological Polar Surface Area181 Ų
Heavy Atom Count48
Formal Charge0
Complexity1320
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameBromocriptine mesylate
Drug LabelBromocriptine 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 IngredientBromocriptine mesylate
Dosage FormTablet; Capsule
RouteOral
Strengtheq 5mg base; eq 2.5mg base
Market StatusPrescription
CompanyLek Pharms; Paddock; Zydus Pharms Usa; Mylan

2 of 6  
Drug NameCycloset
PubMed HealthBromocriptine (By mouth)
Drug ClassesAntidiabetic, Antiparkinsonian, Prolactin Secretion Inhibitor
Drug LabelCYCLOSET 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 IngredientBromocriptine mesylate
Dosage FormTablet
RouteOral
Strengtheq 0.8mg base
Market StatusPrescription
CompanyVeroscience

3 of 6  
Drug NameParlodel
PubMed HealthBromocriptine (By mouth)
Drug ClassesAntidiabetic, Antiparkinsonian, Prolactin Secretion Inhibitor
Drug LabelParlodel (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 IngredientBromocriptine mesylate
Dosage FormTablet; Capsule
RouteOral
Strengtheq 5mg base; eq 2.5mg base
Market StatusPrescription
CompanyUs Pharms Holdings I

4 of 6  
Drug NameBromocriptine mesylate
Drug LabelBromocriptine 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 IngredientBromocriptine mesylate
Dosage FormTablet; Capsule
RouteOral
Strengtheq 5mg base; eq 2.5mg base
Market StatusPrescription
CompanyLek Pharms; Paddock; Zydus Pharms Usa; Mylan

5 of 6  
Drug NameCycloset
PubMed HealthBromocriptine (By mouth)
Drug ClassesAntidiabetic, Antiparkinsonian, Prolactin Secretion Inhibitor
Drug LabelCYCLOSET 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 IngredientBromocriptine mesylate
Dosage FormTablet
RouteOral
Strengtheq 0.8mg base
Market StatusPrescription
CompanyVeroscience

6 of 6  
Drug NameParlodel
PubMed HealthBromocriptine (By mouth)
Drug ClassesAntidiabetic, Antiparkinsonian, Prolactin Secretion Inhibitor
Drug LabelParlodel (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 IngredientBromocriptine mesylate
Dosage FormTablet; Capsule
RouteOral
Strengtheq 5mg base; eq 2.5mg base
Market StatusPrescription
CompanyUs 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]

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No.261\/4A,14\/1,JINNARAM ROAD, A"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q3","strtotime":1691173800,"product":"BROMOCRIPTINE MESYLATE-API","address":"P NO.64 and 65, SY NO.342, ALEAP I E, ,GAJULARAMARAM (V), QUTBULLAPUR (M),,, AP.","city":"HYDERABAD","supplier":"TEVA CZECH","supplierCountry":"CZECH REPUBLIC","foreign_port":"NA","customer":"AIRIS PHARMA","customerCountry":"INDIA","quantity":"0.04","actualQuantity":"0.04","unit":"KGS","unitRateFc":"2500","totalValueFC":"98.6","currency":"USD","unitRateINR":"202771.8","date":"05-Aug-2023","totalValueINR":"8192.8","totalValueInUsd":"98.6","indian_port":"HYDERABAD AIR","hs_no":"29182990","bill_no":"0","productDescription":"API","marketType":"REGULATED MARKET","country":"CZECH REPUBLIC","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"P NO.64 and 65, SY NO.342, ALEAP I E, ,GAJULARAMARAM (V), QUTBULLAPUR (M),,, AP."},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q3","strtotime":1695666600,"product":"BROMOCRIPTINE MESYLATE USP","address":"ZYDUS TOWER, SARKHEJ-GANDHINAGAR,H","city":"AHMEDABAD,GUJARAT","supplier":"TEVA API","supplierCountry":"CZECH REPUBLIC","foreign_port":"PRAGUE - RUZYNE","customer":"ZYDUS LIFESCIENCES LIMITED","customerCountry":"INDIA","quantity":"1.00","actualQuantity":"1","unit":"KGS","unitRateFc":"24000","totalValueFC":"24264.9","currency":"USD","unitRateINR":"2017200","date":"26-Sep-2023","totalValueINR":"2017200","totalValueInUsd":"24264.9","indian_port":"Bombay Air","hs_no":"29396900","bill_no":"8012218","productDescription":"API","marketType":"REGULATED MARKET","country":"CZECH REPUBLIC","selfForZScoreResived":"Pharma Grade","supplierPort":"PRAGUE - RUZYNE","supplierAddress":"PIET HEIN BUILDING PIET HEINKADE 107, 1019 GM AMSTERDAM Amsterdam, Netherlands Netherlands","customerAddress":"ZYDUS TOWER, SARKHEJ-GANDHINAGAR,H"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1698258600,"product":"BROMOCRIPTINE MESYLATE IP","address":"INGA HOUSE","city":"BOMBAY ,MAHARASHTRA","supplier":"TEVA API","supplierCountry":"CZECH REPUBLIC","foreign_port":"PRAGUE - RUZYNE","customer":"INGA LABORATORIES PRIVATE ","customerCountry":"INDIA","quantity":"2.00","actualQuantity":"2","unit":"KGS","unitRateFc":"10750","totalValueFC":"21743.5","currency":"USD","unitRateINR":"905150","date":"26-Oct-2023","totalValueINR":"1810300","totalValueInUsd":"21743.5","indian_port":"Bombay Air","hs_no":"29398000","bill_no":"8477911","productDescription":"API","marketType":"REGULATED MARKET","country":"CZECH REPUBLIC","selfForZScoreResived":"Pharma Grade","supplierPort":"PRAGUE - RUZYNE","supplierAddress":"PIET HEIN BUILDING ,PIET HEINKADE107, 1019 GM A, AMSTERDAM THE NETHERLANDS NETHERLANDS","customerAddress":"INGA HOUSE"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1700591400,"product":"BROMOCRIPTINE MESYLATE USP","address":"ZYDUS TOWER, SARKHEJ-GANDHINAGAR,H","city":"AHMEDABAD,GUJARAT","supplier":"TEVA API","supplierCountry":"CZECH REPUBLIC","foreign_port":"PRAGUE - RUZYNE","customer":"ZYDUS LIFESCIENCES LIMITED","customerCountry":"INDIA","quantity":"1.50","actualQuantity":"1.5","unit":"KGS","unitRateFc":"24000","totalValueFC":"36458.4","currency":"USD","unitRateINR":"2018400","date":"22-Nov-2023","totalValueINR":"3027600","totalValueInUsd":"36458.4","indian_port":"Bombay Air","hs_no":"29396900","bill_no":"8882071","productDescription":"API","marketType":"REGULATED MARKET","country":"CZECH REPUBLIC","selfForZScoreResived":"Pharma Grade","supplierPort":"PRAGUE - RUZYNE","supplierAddress":"PIET HEIN BUILDING PIET HEINKADE 107, 1019 GM AMSTERDAM Amsterdam, , Netherlands Netherlands","customerAddress":"ZYDUS TOWER, SARKHEJ-GANDHINAGAR,H"}]
05-Jan-2021
22-Nov-2023
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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