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    Chemistry

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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
    Dexchloropheniramine Maleate
    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

    Dexchloropheniramine 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 Weight 390.9 g/mol
    Molecular Formula C20H23ClN2O4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count7
    Exact Mass390.1346349 g/mol
    Monoisotopic Mass390.1346349 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 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameDexchlorpheniramine maleate
    PubMed HealthDexchlorpheniramine Maleate (By mouth)
    Drug ClassesRespiratory Agent
    Drug LabelEach 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 IngredientDexchlorpheniramine maleate
    Dosage FormSyrup
    RouteOral
    Strength2mg/5ml
    Market StatusPrescription
    CompanyWockhardt

    2 of 2  
    Drug NameDexchlorpheniramine maleate
    PubMed HealthDexchlorpheniramine Maleate (By mouth)
    Drug ClassesRespiratory Agent
    Drug LabelEach 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 IngredientDexchlorpheniramine maleate
    Dosage FormSyrup
    RouteOral
    Strength2mg/5ml
    Market StatusPrescription
    CompanyWockhardt

    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.

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - SUSPENSION, EXTENDED RELEASE;ORAL - ...DOSAGE - 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**

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