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O-Anisamide, 4-amino-5-bromo-N-[2-(diethylamino)ethyl]-

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Bromopride

Synopsis

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Chemistry

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Also known as: 4093-35-0, Artomey, Valopride, Bromoprida, Viaben, Movipride

Molecular Formula

C₁₄H₂₂BrN₃O₂

Molecular Weight

344.25 g/mol

InChI Key

GIYAQDDTCWHPPL-UHFFFAOYSA-N

FDA UNII

75473V2YZK

Bromopride is a dopamine antagonist used as an antiemetic. Its prokinetic properties are similar to those of metoclopramide. It is unavailable in America or the United Kingdom.

1 2D Structure

Bromopride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-5-bromo-N-[2-(diethylamino)ethyl]-2-methoxybenzamide

2.1.2 InChI

InChI=1S/C14H22BrN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)

2.1.3 InChI Key

GIYAQDDTCWHPPL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN(CC)CCNC(=O)C1=CC(=C(C=C1OC)N)Br

2.2 Other Identifiers

2.2.1 UNII

75473V2YZK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bromoprid

2. Bromopride Dihydrochloride

3. Bromopride Hydrochloride

4. Viaben

2.3.2 Depositor-Supplied Synonyms

1. 4093-35-0

2. Artomey

3. Valopride

4. Bromoprida

5. Viaben

6. Movipride

7. 4-amino-5-bromo-n-(2-(diethylamino)ethyl)-o-anisamide

8. 4-amino-5-bromo-n-[2-(diethylamino)ethyl]-2-methoxybenzamide

9. Val 13081

10. Nsc-758391

11. Emepride

12. 75473v2yzk

13. Bromopride (inn)

14. Ncgc00016646-02

15. Cas-4093-35-0

16. Bromopride [inn]

17. Benzamide, 4-amino-5-bromo-n-(2-(diethylamino)ethyl)-2-methoxy-

18. Benzamide, 4-amino-5-bromo-n-[2-(diethylamino)ethyl]-2-methoxy-

19. Dsstox_cid_25383

20. Dsstox_rid_80841

21. Dsstox_gsid_45383

22. Bromoprida [spanish]

23. O-anisamide, 4-amino-5-bromo-n-[2-(diethylamino)ethyl]-

24. Bromopridum

25. 4-amino-5-bromo-n-(2-(diethylamino)ethyl)-2-methoxybenzamide

26. Bromoprid

27. Emoril

28. Bromopride [inn:dcf]

29. O-anisamide, 4-amino-5-bromo-n-(2-(diethylamino)ethyl)-

30. Bromopridum [inn-latin]

31. Bromoprida [inn-spanish]

32. Sr-01000841242

33. Einecs 223-842-2

34. Brn 2381893

35. Unii-75473v2yzk

36. N-(diethylaminoethyl)-2-methoxy-4-amino-5-bromobenzamide

37. Bromopride-[d3]

38. Movipride (tn)

39. Prestwick_61

40. Spectrum_001394

41. Bromopride [mi]

42. Prestwick0_000704

43. Prestwick1_000704

44. Prestwick2_000704

45. Prestwick3_000704

46. Spectrum2_001527

47. Spectrum3_001559

48. Spectrum4_000726

49. Spectrum5_000970

50. Bromopride [mart.]

51. Bromopride [who-dd]

52. Schembl54497

53. Bspbio_000887

54. Bspbio_003038

55. Kbiogr_000992

56. Kbioss_001874

57. Mls002153965

58. Divk1c_000317

59. Spectrum1503108

60. Spbio_001314

61. Spbio_002808

62. Bpbio1_000977

63. Chembl399510

64. Dtxsid0045383

65. Chebi:95304

66. Hms500p19

67. Kbio1_000317

68. Kbio2_001874

69. Kbio2_004442

70. Kbio2_007010

71. Kbio3_002538

72. Ninds_000317

73. Hms1570m09

74. Hms1922e21

75. Hms2097m09

76. Hms2230k23

77. Hms3374m06

78. Hms3714m09

79. Pharmakon1600-01503108

80. Hy-b1164

81. Zinc2038104

82. Tox21_110543

83. Bdbm50247887

84. Ccg-39305

85. Nsc758391

86. Akos015994598

87. Tox21_110543_1

88. Cs-4764

89. Db09018

90. Hs-0004

91. Nsc 758391

92. Idi1_000317

93. Ncgc00016646-01

94. Ncgc00016646-05

95. Ncgc00095309-01

96. Smr001233304

97. Sbi-0051774.p002

98. Ab00052316

99. Ft-0663848

100. D07101

101. Ab00052316_08

102. A917874

103. Q1958189

104. Sr-01000841242-2

105. Sr-01000841242-3

106. Brd-k73642618-001-05-9

107. Brd-k73642618-001-08-3

108. 4-amino-5-bromo-n-[2-(diethylamino)ethyl]-2-methoxybenzamide #

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₂₂BrN₃O₂
Molecular Weight	344.25 g/mol
XLogP3	2.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	7
Exact Mass	343.08954 g/mol
Monoisotopic Mass	343.08954 g/mol
Topological Polar Surface Area	67.6 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	300
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	1

4 Drug and Medication Information

4.1 Drug Indication

Bromopride in indicated in the treatment of nausea and vomiting, including PONV (post-operative nausea and vomiting), gastroesophageal reflux disease (GERD/GORD), as well as endoscopy preparation and radiographic studies of the GI tract.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)

Dopamine Antagonists

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)

5.2 ATC Code

A - Alimentary tract and metabolism

A03 - Drugs for functional gastrointestinal disorders

A03F - Propulsives

A03FA - Propulsives

A03FA04 - Bromopride

5.3 Absorption, Distribution and Excretion

Clearance

Renal, 10-14% as original compound.

5.4 Metabolism/Metabolites

Hepatic.

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