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    Pramoxine HCl

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: 637-58-1, Pramoxine hcl, Pramocaine hydrochloride, Prax lotion, Tronothane, Pramocaine (hydrochloride)
    Molecular Formula
    C17H28ClNO3
    Molecular Weight
    329.9  g/mol
    InChI Key
    SYCBXBCPLUFJID-UHFFFAOYSA-N
    FDA UNII
    88AYB867L5
    Pramocaine Hydrochloride is the hydrochloride salt form of pramoxine, a morpholine derivative with local anesthetic property. Pramocaine hydrochloride decreases the permeability of the neuronal membrane to sodium ions by reversibly binding to and inhibiting voltage-gated sodium channels. This results in stabilization of the membrane and, thereby inhibiting the ionic fluxes required for membrane depolarization, hence resulting in the failure to initiate a propagated action potential and subsequent conduction blockade.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[3-(4-butoxyphenoxy)propyl]morpholine;hydrochloride
    2.1.2 InChI
    InChI=1S/C17H27NO3.ClH/c1-2-3-12-20-16-5-7-17(8-6-16)21-13-4-9-18-10-14-19-15-11-18;/h5-8H,2-4,9-15H2,1H3;1H
    2.1.3 InChI Key
    SYCBXBCPLUFJID-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCCOC1=CC=C(C=C1)OCCCN2CCOCC2.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    88AYB867L5
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-(3-(4-butoxyphenoxy)propyl)morpholine

    2. 4-(3-(p-butoxyphenoxy)propyl)morpholine

    3. Balsabit

    4. Fleet Pain Relief

    5. Itch-x

    6. Pramegel

    7. Pramocaine

    8. Pramocaine Hydrochloride

    9. Pramox

    10. Pramoxine

    11. Prax

    12. Proctofoam

    13. Tronolane

    14. Tronothane

    2.3.2 Depositor-Supplied Synonyms

    1. 637-58-1

    2. Pramoxine Hcl

    3. Pramocaine Hydrochloride

    4. Prax Lotion

    5. Tronothane

    6. Pramocaine (hydrochloride)

    7. Morpholine, 4-[3-(4-butoxyphenoxy)propyl]-, Hydrochloride

    8. 4-[3-(4-butoxyphenoxy)propyl]morpholine Hydrochloride

    9. Nsc-25573

    10. 4-(3-(4-butoxyphenoxy)propyl)morpholine Hydrochloride

    11. Pramoxine Hydrochloride [usp]

    12. Mls000028604

    13. Tronolane

    14. 88ayb867l5

    15. 4-(3-(p-butoxyphenoxy)propyl)morpholine Hydrochloride

    16. 4-[3-(4-butoxyphenoxy)propyl]morpholine;hydrochloride

    17. 637-58-1 (hcl)

    18. Morpholine, 4-(3-(4-butoxyphenoxy)propyl)-, Hydrochloride

    19. Smr000058670

    20. Dsstox_cid_27757

    21. Dsstox_rid_82534

    22. Dsstox_gsid_47777

    23. Pramoxine Hydrochloride (usp)

    24. Tronothane Hydrochloride

    25. Proctofoam-ns

    26. Hsdb 7220

    27. Ncgc00016529-01

    28. Cas-637-58-1

    29. Einecs 211-293-1

    30. Nsc 25573

    31. 4-[3-(p-butoxyphenoxy)propyl]morpholine Hydrochloride

    32. Unii-88ayb867l5

    33. Sr-01000000243

    34. Pramoxine, Hcl

    35. Tronothane (tn)

    36. Prestwick_1044

    37. P-butoxyphenyl Gamma-morpholinopropyl Ether Hydrochloride

    38. Gamma-morpholinopropyl 4-n-butoxyphenyl Ether Hydrochloride

    39. Opera_id_1593

    40. Pramoxine Hcl [inci]

    41. Mls002222295

    42. Schembl180542

    43. Spectrum1501139

    44. Amy585

    45. Chebi:8358

    46. Chembl1201171

    47. Dtxsid2047777

    48. Morpholine, 4-(3-(p-butoxyphenoxy)propyl)-, Hydrochloride

    49. Hms1570o13

    50. Hms1921j07

    51. Pharmakon1600-01501139

    52. Hy-b1319

    53. Nsc25573

    54. Pramoxine Hydrochloride [mi]

    55. Tox21_110477

    56. Mfcd00054323

    57. Nsc757847

    58. S4092

    59. Pramoxine Hydrochloride [hsdb]

    60. Akos015895041

    61. Tox21_110477_1

    62. Ac-2094

    63. Ccg-212937

    64. Cs-4643

    65. Nsc-757847

    66. Pramoxine Hydrochloride [vandf]

    67. Wln: T6n Dotj A3or Do4 &gh

    68. Pramocaine Hydrochloride [mart.]

    69. Pramoxine Hydrochloride [usp-rs]

    70. Ncgc00016529-07

    71. Ncgc00094907-01

    72. Ncgc00094907-02

    73. Ncgc00094907-03

    74. Pramocaine Hydrochloride [who-dd]

    75. As-12691

    76. Db-054541

    77. Ft-0603501

    78. Pramoxine Hydrochloride [orange Book]

    79. Sw197114-3

    80. Vu0239834-5

    81. D00739

    82. D97624

    83. Epifoam Component Pramoxine Hydrochloride

    84. Pramoxine Hydrochloride [usp Monograph]

    85. A834509

    86. Pramosone Component Pramoxine Hydrochloride

    87. Pramoxine Hydrochloride Component Of Epifoam

    88. Pramoxine Hydrochloride, Analytical Standard, >=98%

    89. Q-100732

    90. Sr-01000000243-3

    91. Pramoxine Hydrochloride Component Of Pramosone

    92. Proctofoam Hc Component Pramoxine Hydrochloride

    93. Q27269918

    94. 4-[3-(4-butoxyphenoxy)propyl]morpholin-4-ium;chloride

    95. Pramoxine Hydrochloride Component Of Proctofoam Hc

    96. P-butoxyphenyl .gamma.-morpholinopropyl Ether Hydrochloride

    97. .gamma.-morpholinopropyl 4-n-butoxyphenyl Ether Hydrochloride

    98. 4-[3-(4-butoxyphenoxy)propyl]morpholine Hydrochloride (1:1)

    99. Morpholine, 4-[3-(p-n-butoxyphenoxy )propyl]-, Hydrochloride

    100. 4-n-butoxyphenyl.gamma.-morpholinopropyl Ether Hydrochloride

    101. Morpholine, 4-[3-(4-butoxyphenoxy)propyl]-, Hydrochloride (1:1)

    102. 4-[3-(4-butoxyphenoxy)propyl]morpholine Chloride;pramocaine Hydrochloride

    103. Pramoxine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    104. Pramoxine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

    2.4 Create Date
    2005-03-27
    3 Chemical and Physical Properties
    Molecular Weight 329.9 g/mol
    Molecular Formula C17H28ClNO3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count9
    Exact Mass329.1757714 g/mol
    Monoisotopic Mass329.1757714 g/mol
    Topological Polar Surface Area30.9 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity248
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    Anesthetic (local)

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1376

    Indicated for the symptomatic relief of: hemorrhoids, anorectal inflammation and anorectal pain. (these medications /including pramoxine/ are effective when applied to the anal, periana, or anorectal areas. However, they are not likely to relieve symptoms associated with conditions confined to the rectum, which lacks sensory nerve fibers.) /Included in US product labeling/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 153

    Pramoxine preparations are used topically for the temporary relief of pain and itching associated with dermatoses; rashes due to poison ivy, poison oak, poison sumac, insect bites; minor burns; anogenital pruritus or irritation; and fissures; or hemorrhoids. The drug should not be used for bronchoscopy or gastroscopy since it is not sufficiently potent to abolish the gag reflex.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3414

    4.2 Drug Warning

    Local effects, such as burning or stinging, may occur following topical application of pramoxine. The drug has a low index of sensitization, and cross-sensitization with other local anesthetics is unlikely.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3414

    Topical pramoxine preparations should not be used in or near the eyes or nose.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3414

    The preparations should not be applied to extensive areas of skin and are not for prolonged use. The aerosol foam for rectal administration should not be used longer than 4 consecutive weeks.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3414

    If pramoxine preparations are used for self-medication and the condition worsens or symptoms persist for prolonged periods (e.g., for more than 7 days) or clear and occur again within a few days, the drug should be discontinued and a physician consulted.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3414

    If rectal bleeding occurs during use of pramoxine for pain and itching of hemorrhoids or if erythema, irritation, swelling, or pain occurs during use of pramoxine preparations, the drug should be discontinued and a physician consulted.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3414

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anesthetics, Local

    Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate. (See all compounds classified as Anesthetics, Local.)

    5.2 Absorption, Distribution and Excretion

    ... These agents are readily absorbed through mucous membranes into the systemic circulation. The rate of absorption is influenced by the vascularity or rate of blood flow at the site of application, the total dosage (concentration and volume) administered, and the duration of exposure. ... /Local anesthetics/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 154

    5.3 Mechanism of Action

    Local anesthetics block both the initiation and conduction of nerve impulses by decreasing the neuronal membrane's permeability to sodium ions. This reversibly stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and subsequent conduction blockade. /Local anesthetics/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 154