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Chemistry

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Also known as: 2391-03-9, Disomer, (+)-brompheniramine maleate, (s)-brompheniramine maleate, Brompheniramine d-form maleate, Chebi:59273
Molecular Formula
C20H23BrN2O4
Molecular Weight
435.3  g/mol
InChI Key
SRGKFVAASLQVBO-DASCVMRKSA-N
FDA UNII
BPA9UT29BS

Dexbrompheniramine Maleate
Dexbrompheniramine Maleate is the maleate salt form of dexbrompheniramine, an alkylamine derivative with anticholinergic and sedative properties. Dexbrompheniramine is a histamine H1-receptor antagonist that competes with histamine for the H1-receptor sites on effector cells in the gastrointestinal tract, blood vessels and respiratory tract. The antagonistic action of this agent blocks the activities of endogenous histamine, which subsequently leads to temporary relief from the negative histamine-mediated symptoms of allergic reaction such as bronchoconstriction, vasodilation, increased capillary permeability and spasmodic contractions of gastrointestinal smooth muscle.
1 2D Structure

Dexbrompheniramine Maleate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3S)-3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine;(Z)-but-2-enedioic acid
2.1.2 InChI
InChI=1S/C16H19BrN2.C4H4O4/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-9,11,15H,10,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t15-;/m0./s1
2.1.3 InChI Key
SRGKFVAASLQVBO-DASCVMRKSA-N
2.1.4 Canonical SMILES
CN(C)CCC(C1=CC=C(C=C1)Br)C2=CC=CC=N2.C(=CC(=O)O)C(=O)O
2.1.5 Isomeric SMILES
CN(C)CC[C@@H](C1=CC=C(C=C1)Br)C2=CC=CC=N2.C(=C\C(=O)O)\C(=O)O
2.2 Other Identifiers
2.2.1 UNII
BPA9UT29BS
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Dexbrompheniramine

2. Disophrol

2.3.2 Depositor-Supplied Synonyms

1. 2391-03-9

2. Disomer

3. (+)-brompheniramine Maleate

4. (s)-brompheniramine Maleate

5. Brompheniramine D-form Maleate

6. Chebi:59273

7. Dexbrompheniramine Fumarate

8. Bpa9ut29bs

9. 2391-03-9 (maleate)

10. Dsstox_cid_27795

11. Dsstox_rid_82567

12. Dsstox_gsid_47818

13. Dexbrompheniramine Maleate (usp)

14. Dexbrompheniramine Maleate [usp]

15. Disomer Maleate

16. (3s)-3-(4-bromophenyl)-n,n-dimethyl-3-pyridin-2-ylpropan-1-amine Maleate

17. 2-pyridinepropanamine, G-(4-bromophenyl)-n,n-dimethyl-, (gs)-,(2z)-2-butenedioate (1:1)

18. Cas-2391-03-9

19. Ncgc00162100-02

20. Alahist Ir

21. Alahist Pe

22. Disomer (tn)

23. D-brompheniramine Maleate

24. Unii-bpa9ut29bs

25. Mls001401374

26. Schembl217770

27. 3-(2-hydroxyphenyl)benzoicacid

28. Chembl1200638

29. Dtxsid6047818

30. (+)-brompheniramine Maleate Salt

31. Hms2051f10

32. Hms2235o07

33. Hms3260p05

34. Einecs 219-236-2

35. Tox21_112000

36. Tox21_500232

37. Bdbm50247924

38. Akos015962824

39. Tox21_112000_1

40. Ac-1161

41. Ccg-101017

42. Lp00232

43. Nc00267

44. Ncgc00015146-11

45. Ncgc00093697-01

46. Ncgc00260917-01

47. Dexbrompheniramine Maleate [mart.]

48. Dexbrompheniramine Maleate [vandf]

49. Smr000471616

50. Dexbrompheniramine Maleate [usp-rs]

51. Dexbrompheniramine Maleate [who-dd]

52. Brompheniramine D-form Maleate [mi]

53. Eu-0100232

54. B 5275

55. D03704

56. Dexbrompheniramine Maleate [orange Book]

57. Dexbrompheniramine Maleate [usp Monograph]

58. Sr-01000075719

59. Disobrom Component Dexbrompheniramine Maleate

60. Disophrol Component Dexbrompheniramine Maleate

61. Drixoral Component Dexbrompheniramine Maleate

62. Resporal Component Dexbrompheniramine Maleate

63. Sr-01000075719-1

64. Brompheril Component Dexbrompheniramine Maleate

65. Dexbrompheniramine Maleate Component Of Disobrom

66. Dexbrompheniramine Maleate Component Of Drixoral

67. Dexbrompheniramine Maleate Component Of Resporal

68. Q27126583

69. Dexbrompheniramine Maleate Component Of Brompheril

70. Dexbrompheniramine Maleate Component Of Disophrol

71. Drixoral Plus Component Dexbrompheniramine Maleate

72. Dexbrompheniramine Maleate Component Of Drixoral Plus

73. (+)-2-(p-bromo-alpha-(2-dimethylaminoethyl)benzyl)pyridine Maleate

74. (s)-1-(p-bromophenyl)-1-(2-pyridyl)-3-dimethylaminopropane Maleate

75. (s)-2-(p-bromo-alpha-(2-dimethylaminoethyl)benzyl)pyridine Maleate

76. (+)-2-(p-bromo-alpha-(2-(dimethylamino)ethyl)benzyl)pyridine Maleate

77. (+)-3-(4-bromophenyl)-n,n-dimethyl-3-(2-pyridinyl)-1-propanamine Maleate

78. (+)-3-(p-bromophenyl)-3-(2-pyridyl)-n,n-dimethylpropylamine Maleate

79. (s)-3-(4-bromophenyl)-n,n-dimethyl-3-(2-pyridinyl)-1-propanamine Maleate

80. (s)-3-(p-bromophenyl)-3-(2-pyridyl)-n,n-dimethylpropylamine Maleate

81. (+)-2-(p-bromo-.alpha.-(2-(dimethylamino)ethyl)benzyl)pyridine Maleate (1:1)

82. (+)-2-(p-bromo-alpha-(2-(dimethylamino)ethyl)benzyl)pyridine Maleate (1:1)

83. (+)-3-(4-bromophenyl)-n,n-dimethyl-3-(pyridin-2-yl)propan-1-amine Maleate

84. (3s)-3-(4-bromophenyl)-n,n-dimethyl-3-(pyridin-2-yl)propan-1-amine (2z)-but-2-enedioate

85. (3s)-3-(4-bromophenyl)-n,n-dimethyl-3-(pyridin-2-yl)propan-1-amine Maleate

86. (3s)-3-(4-bromophenyl)-n,n-dimethyl-3-pyridin-2-ylpropan-1-amine;(z)-but-2-enedioic Acid

87. (s)-2-(p-bromo-alpha-(2-(dimethylamino)ethyl)benzyl)pyridinium (z)-maleate (1:1)

88. (s)-3-(4-bromophenyl)-n,n-dimethyl-3-(pyridin-2-yl)propan-1-amine Maleate

89. Dexbrompheniramine Maleate, United States Pharmacopeia (usp) Reference Standard

90. Pyridine, 2-(p-bromo-alpha-(2-(dimethylamino)ethyl)benzyl)-, Maleate (1:1), (s)-

91. 2-pyridinepropanamine, G-(4-bromophenyl)-n,n-dimethyl-, (s)-, (z)-2-butenedioate (1:1)

92. 2-pyridinepropanamine, Gamma-(4-bromophenyl)-n,n-dimethyl-, (s)-, (z)-2-butenedioate (1:1)

2.4 Create Date
2006-04-28
3 Chemical and Physical Properties
Molecular Weight 435.3 g/mol
Molecular Formula C20H23BrN2O4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Exact Mass434.08412 g/mol
Monoisotopic Mass434.08412 g/mol
Topological Polar Surface Area90.7 Ų
Heavy Atom Count27
Formal Charge0
Complexity368
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Histamine H1 Antagonists

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)


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DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : DEXBROMPHENIRAMINE MALEATE AND PSEUDOEPHEDRINE SULFATE

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 6MG;120MG

Packaging :

Approval Date : 2013-02-27

Application Number : 78648

Regulatory Info : DISCN

Registration Country : USA

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DEXBROMPHENIRAMINE MALEATE

Brand Name : DISOMER

Dosage Form : TABLET;ORAL

Dosage Strength : 2MG

Packaging :

Approval Date : 1982-01-01

Application Number : 11814

Regulatory Info : DISCN

Registration Country : USA

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AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE

Brand Name : DISOMER

Dosage Form : SYRUP;ORAL

Dosage Strength : 2MG/5ML

Packaging :

Approval Date : 1982-01-01

Application Number : 11814

Regulatory Info : DISCN

Registration Country : USA

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04

Bayer AG

Germany
AES 2024
Not Confirmed
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Bayer AG

Germany
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AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : DISOPHROL

Dosage Form : TABLET;ORAL

Dosage Strength : 2MG;60MG

Packaging :

Approval Date : 1982-01-01

Application Number : 12394

Regulatory Info : DISCN

Registration Country : USA

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05

Copley Scientific

United Kingdom
AES 2024
Not Confirmed
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Copley Scientific

United Kingdom
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AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : BROMPHERIL

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 6MG;120MG

Packaging :

Approval Date : 1987-01-22

Application Number : 89116

Regulatory Info : DISCN

Registration Country : USA

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06

Merck & Co

U.S.A
AES 2024
Not Confirmed
arrow

Merck & Co

U.S.A
arrow
AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : DRIXORAL

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 6MG;120MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

Packaging :

Approval Date : 1982-09-13

Application Number : 13483

Regulatory Info : DISCN

Registration Country : USA

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07

Merck & Co

U.S.A
AES 2024
Not Confirmed
arrow

Merck & Co

U.S.A
arrow
AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : DISOPHROL

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 6MG;120MG

Packaging :

Approval Date : 1982-09-13

Application Number : 13483

Regulatory Info : DISCN

Registration Country : USA

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08

Merck & Co

U.S.A
AES 2024
Not Confirmed
arrow

Merck & Co

U.S.A
arrow
AES 2024
Not Confirmed

ACETAMINOPHEN; DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : DRIXORAL PLUS

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 500MG;3MG;60MG

Packaging :

Approval Date : 1987-05-22

Application Number : 19453

Regulatory Info : DISCN

Registration Country : USA

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09

AES 2024
Not Confirmed
arrow
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AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : RESPORAL

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 6MG;120MG

Packaging :

Approval Date : 1988-06-16

Application Number : 89139

Regulatory Info : DISCN

Registration Country : USA

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10

Sandoz B2B

Switzerland
AES 2024
Not Confirmed
arrow

Sandoz B2B

Switzerland
arrow
AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : DISOBROM

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 6MG;120MG

Packaging :

Approval Date : 1991-09-30

Application Number : 70770

Regulatory Info : DISCN

Registration Country : USA

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FDA Orange Book

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01

AVANTHI INC

U.S.A
AES 2024
Not Confirmed
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AVANTHI INC

U.S.A
arrow
AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : DEXBROMPHENIRAMINE MALEATE AND PSEUDOEPHEDRINE SULFATE

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 6MG;120MG

Approval Date : 2013-02-27

Application Number : 78648

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

blank

02

SCHERING

Germany
AES 2024
Not Confirmed
arrow

SCHERING

Germany
arrow
AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE

Brand Name : DISOMER

Dosage Form : TABLET;ORAL

Dosage Strength : 2MG

Approval Date : 1982-01-01

Application Number : 11814

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

blank

03

SCHERING

Germany
AES 2024
Not Confirmed
arrow

SCHERING

Germany
arrow
AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE

Brand Name : DISOMER

Dosage Form : SYRUP;ORAL

Dosage Strength : 2MG/5ML

Approval Date : 1982-01-01

Application Number : 11814

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

blank

04

SCHERING

Germany
AES 2024
Not Confirmed
arrow

SCHERING

Germany
arrow
AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : DISOPHROL

Dosage Form : TABLET;ORAL

Dosage Strength : 2MG;60MG

Approval Date : 1982-01-01

Application Number : 12394

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

blank

05

COPLEY PHARM

United Kingdom
AES 2024
Not Confirmed
arrow

COPLEY PHARM

United Kingdom
arrow
AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : BROMPHERIL

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 6MG;120MG

Approval Date : 1987-01-22

Application Number : 89116

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

blank

06

AES 2024
Not Confirmed
arrow
arrow
AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : DRIXORAL

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 6MG;120MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

Approval Date : 1982-09-13

Application Number : 13483

RX/OTC/DISCN : DISCN

RLD : Yes

TE Code :

blank

07

AES 2024
Not Confirmed
arrow
arrow
AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : DISOPHROL

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 6MG;120MG

Approval Date : 1982-09-13

Application Number : 13483

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

blank

08

AES 2024
Not Confirmed
arrow
arrow
AES 2024
Not Confirmed

ACETAMINOPHEN; DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : DRIXORAL PLUS

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 500MG;3MG;60MG

Approval Date : 1987-05-22

Application Number : 19453

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

blank

09

AES 2024
Not Confirmed
arrow
arrow
AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : RESPORAL

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 6MG;120MG

Approval Date : 1988-06-16

Application Number : 89139

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

blank

10

SANDOZ

Switzerland
AES 2024
Not Confirmed
arrow

SANDOZ

Switzerland
arrow
AES 2024
Not Confirmed

DEXBROMPHENIRAMINE MALEATE; PSEUDOEPHEDRINE SULFATE

Brand Name : DISOBROM

Dosage Form : TABLET, EXTENDED RELEASE;ORAL

Dosage Strength : 6MG;120MG

Approval Date : 1991-09-30

Application Number : 70770

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

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