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(+)-Chlorpheniramine maleate

Synopsis, Chemistry

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DRUG PRODUCT COMPOSITION

SUSPENSION, EXTENDED RELEASE;ORAL - EQ 8MG MALEATE/5ML;EQ 10MG BITARTRATE/5ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, SUSPENSION, EXTENDED RELEASE;ORAL - EQ 2.8MG BASE/5ML;EQ 14.7MG BASE/5ML, SYRUP;ORAL - 2MG/5ML

SUSPENSION, EXTENDED RELEASE;ORAL - EQ 8MG MALEATE/5ML;EQ 10MG BITARTRATE/5ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
SUSPENSION, EXTENDED RELEASE;ORAL - EQ 2.8MG BASE/5ML;EQ 14.7MG BASE/5ML
SYRUP;ORAL - 2MG/5ML

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Also known as: 2438-32-6, Polaramine, (+)-chlorpheniramine maleate, D-chlorpheniramine maleate, Dexchloropheniramine maleate, Mylaramine

Molecular Formula

C₂₀H₂₃ClN₂O₄

Molecular Weight

390.9 g/mol

InChI Key

DBAKFASWICGISY-DASCVMRKSA-N

FDA UNII

B10YD955QW

Dexchlorpheniramine Maleate is the maleate salt form of dexchlorpheniramine, an alkylamine, and first-generation histamine antagonist with anti-allergic activity. Dexchlorpheniramine maleate competitively blocks H1 receptors, thereby preventing the actions of histamine on bronchial smooth muscle, capillaries and gastrointestinal (GI) smooth muscle. This prevents histamine-induced bronchoconstriction, vasodilation, increased capillary permeability, and GI smooth muscle spasms.

1 2D Structure

(+)-Chlorpheniramine maleate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(Z)-but-2-enedioic acid;(3S)-3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine

2.1.2 InChI

InChI=1S/C16H19ClN2.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

DBAKFASWICGISY-DASCVMRKSA-N

2.1.4 Canonical SMILES

CN(C)CCC(C1=CC=C(C=C1)Cl)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)Cl)C2=CC=CC=N2.C(=C\C(=O)O)\C(=O)O

2.2 Other Identifiers

2.2.1 UNII

B10YD955QW

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dexchlorpheniramine

2. Dexchlorpheniramine Maleate (1:1), (+-)-isomer

3. Dexchlorpheniramine Maleate (1:1), (r)-isomer

4. Dexchlorpheniramine Maleate (1:1), (s)-isomer

5. Dexchlorpheniramine Monohydrochloride

6. Dexchlorpheniramine Sodium Maleate (1:1)

7. Dexchlorpheniramine, (+-)-isomer

8. Dexchlorpheniramine, (r)-isomer

9. Dexchlorpheniramine, Monohydrochloride, (s)-isomer

10. Dexclor

11. Dexclorfeniramine

12. Dextrochlorpheniramine Maleate

13. Polaramin

14. Polaramine

15. Polargen Td

16. Polaronil

2.3.2 Depositor-Supplied Synonyms

1. 2438-32-6

2. Polaramine

3. (+)-chlorpheniramine Maleate

4. D-chlorpheniramine Maleate

5. Dexchloropheniramine Maleate

6. Mylaramine

7. Dexchlorpheniramine (maleate)

8. Chlorpheniramine D-form Maleate

9. S-(+)-chlorpheniramine Maleate Salt

10. Dexchlorpheniramine Maleate, Usp

11. Chebi:4465

12. B10yd955qw

13. Chlorpheniramine Maleate, (s)-

14. Dexchlorpheniramine Maleate [usp]

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

16. Nsc-759156

17. Dextrochlorpheniramine Maleate

18. Dexchlorpheniramine Maleate (usp)

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

20. (gamma-(4-chlorophenyl)-pyridine-2-propyl)(dimethyl)ammonium Hydrogen (z)-maleate

21. Sr-01000075763

22. Unii-b10yd955qw

23. Polar Amine

24. S-(+)-chlorpheniramine Maleate

25. Rescon Jr

26. Rescon Mx

27. Mylaramine (tn)

28. Polaramine (tn)

29. (s)-chlorpheniramine Maleate Salt

30. Einecs 219-450-6

31. Mfcd00079046

32. Dexchlorpheniraminmaleat

33. Mls001401384

34. Schembl119500

35. Chembl1200927

36. Dtxsid001017216

37. Hms2052e15

38. Hms2233i15

39. Hms3260f10

40. D-chlorpheniramine Maleate (jp17)

41. Hy-b1062

42. Tox21_500264

43. Bdbm50247890

44. (+)-2-(p-chloro-alpha-(2-(dimethylamino)ethyl)benzyl)pyridine Maleate (1:1)

45. Akos015962825

46. Ccg-101121

47. Cs-4618

48. Db09555

49. Lp00264

50. Nc00371

51. Nsc 759156

52. (2z)-but-2-enedioic Acid; [(3s)-3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine

53. D-chlorpheniramine Maleate [jan]

54. Ncgc00093722-01

55. Ncgc00093722-02

56. Ncgc00093722-03

57. Ncgc00260949-01

58. 2-pyridinepropanamine, .gamma.-(4-chlorophenyl)-n,n-dimethyl-, (s)-, (z)-2-butenedioate (1:1)

59. Ac-19009

60. As-17464

61. Smr000471617

62. Dexchlorpheniramine Maleate [vandf]

63. Dexchlorpheniramine Maleate [usp-rs]

64. Dexchlorpheniramine Maleate [who-dd]

65. Chlorpheniramine D-form Maleate [mi]

66. Eu-0100264

67. C 4915

68. C07783

69. D00668

70. Dexchlorpheniramine Maleate [ep Impurity]

71. Dexchlorpheniramine Maleate [orange Book]

72. 438d326

73. A924268

74. Dexchlorpheniramine Maleate [ep Monograph]

75. Dexchlorpheniramine Maleate [usp Monograph]

76. Sr-01000075763-1

77. Sr-01000075763-4

78. Q27106393

79. (gammas)-gamma-(4-chlorophenyl)-n,n-dimethyl-2-pyridinepropanamine Maleate

80. Dexchlorpheniramine Maleate, European Pharmacopoeia (ep) Reference Standard

81. Gammas-(4-chlorophenyl)-n,n-dimethyl-2-pyridinepropanamine, 2z-butenedioate

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

83. Dexchlorpheniramine Maleate, United States Pharmacopeia (usp) Reference Standard

84. Pyridine, 2-(p-chloro-alpha-(2-(dimethylamino)ethyl)benzyl)-, Maleate (1:1), (+)-

85. 2-pyridinepropanamine, Gamma-(4-chlorophenyl)-n,n-dimethyl-, (s)-, (z)-2-butenedioate (1:1)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₃ClN₂O₄
Molecular Weight	390.9 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Exact Mass	390.1346349 g/mol
Monoisotopic Mass	390.1346349 g/mol
Topological Polar Surface Area	90.7 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	368
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Dexchlorpheniramine maleate
PubMed Health	Dexchlorpheniramine Maleate (By mouth)
Drug Classes	Respiratory Agent
Drug Label	Each 5 mL (teaspoonful) contains:Dexchlorpheniramine Maleate, USP2 mgAlcohol not more than7.0%Dexchlorpheniramine Maleate, USP, an antihistamine agent, is a white, odorless crystalline powder that is freely soluble in water. The molecular formula is...
Active Ingredient	Dexchlorpheniramine maleate
Dosage Form	Syrup
Route	Oral
Strength	2mg/5ml
Market Status	Prescription
Company	Wockhardt

2 of 2
Drug Name	Dexchlorpheniramine maleate
PubMed Health	Dexchlorpheniramine Maleate (By mouth)
Drug Classes	Respiratory Agent
Drug Label	Each 5 mL (teaspoonful) contains:Dexchlorpheniramine Maleate, USP2 mgAlcohol not more than7.0%Dexchlorpheniramine Maleate, USP, an antihistamine agent, is a white, odorless crystalline powder that is freely soluble in water. The molecular formula is...
Active Ingredient	Dexchlorpheniramine maleate
Dosage Form	Syrup
Route	Oral
Strength	2mg/5ml
Market Status	Prescription
Company	Wockhardt

4.2 Drug Indication

Dexchlorpheniramine can be used in the treatment of perennial and seasonal allergic rhinitis, vasomotor rhiniti, allergic conjunctivitis due to inhalant allergens and foods, mild uncomplicated allergic skin manifestations of urticaria and angioedema, amelioration of allergic reactions to blood or plasma, and dermographism.

5 Pharmacology and Biochemistry

5.1 Pharmacology

In allergic reactions, an allergen binds to IgE antibodies on mast cells and basophils. Once this occurs IgE receptors crosslink with each other triggering a series of events that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Dexchlorpheniramine, is a histamine H1 antagonist of the alkylamine class. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.

5.2 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.)

5.3 Absorption, Distribution and Excretion

Absorption

Oral bioavailability in rats 40.5%

Route of Elimination

Renal excretion

Volume of Distribution

321L

Clearance

9.8L/h

5.4 Metabolism/Metabolites

Hepatic metabolism. Major metabolism by CYP 2D6 and minor metabolism by 3A4, 2C11 and 2B1.

5.5 Biological Half-Life

20-30 h

5.6 Mechanism of Action

Competes with histamine for H1-receptor sites on effector cells in the gastrointestinal tract, blood vessels, and respiratory tract. Dexchlorpheniramine is the predominant active isomer of chlorpheniramine and is approximately twice as active as the racemic compound.