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    Chemistry

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    Also known as: 2016-36-6, Syrap, (2-hydroxyethyl)trimethylammonium salicylate, Choline salicylic acid salt, Salicylic acid choline salt, Choline, salicylate (salt)
    Molecular Formula
    C12H19NO4
    Molecular Weight
    241.28  g/mol
    InChI Key
    UDKCHVLMFQVBAA-UHFFFAOYSA-M
    FDA UNII
    KD510K1IQW
    Choline Salicylate
    Choline Salicylate is the choline salt of salicylic acid, a nonsteroidal anti-inflammatory drug (NSAID), with analgesic, antipyretic, anti-inflammatory, anti-rheumatic and immunomodulating activities. Upon oral administration, salicylic acid irreversibly acetylates cyclooxygenases I and II, thereby inhibiting prostaglandin (PG) synthesis and the PG-associated inflammation, fever and pain. This agent may induce cancer cell apoptosis and modulate the immune response.
    1 2D Structure

    Choline Salicylate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-carboxyphenolate;2-hydroxyethyl(trimethyl)azanium
    2.1.2 InChI
    InChI=1S/C7H6O3.C5H14NO/c8-6-4-2-1-3-5(6)7(9)10;1-6(2,3)4-5-7/h1-4,8H,(H,9,10);7H,4-5H2,1-3H3/q;+1/p-1
    2.1.3 InChI Key
    UDKCHVLMFQVBAA-UHFFFAOYSA-M
    2.1.4 Canonical SMILES
    C[N+](C)(C)CCO.C1=CC=C(C(=C1)C(=O)O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    KD510K1IQW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Mundasal

    2. Mundisal

    2.3.2 Depositor-Supplied Synonyms

    1. 2016-36-6

    2. Syrap

    3. (2-hydroxyethyl)trimethylammonium Salicylate

    4. Choline Salicylic Acid Salt

    5. Salicylic Acid Choline Salt

    6. Choline, Salicylate (salt)

    7. Cholin Salicylate

    8. Salicylic Acid, Ion(1-), Choline

    9. Choline Subsalicylate

    10. 2-hydroxy-n,n,n-trimethylethanaminium 2-hydroxybenzoate

    11. Ethanaminium, 2-hydroxy-n,n,n-trimethyl-, Salt With 2-hydroxybenzoic Acid (1:1)

    12. Kd510k1iqw

    13. Arthropan

    14. 2-hydroxy-n,n,n-trimethylethanaminium Salt With 2-hydroxybenzoic Acid (1:1)

    15. Actasal

    16. Artrobione

    17. Mundisal

    18. Salicol

    19. Satibon

    20. Arret

    21. 2-hydroxybenzoate;2-hydroxyethyl(trimethyl)azanium

    22. 2-carboxyphenolate;2-hydroxyethyl(trimethyl)azanium

    23. Choline Salicylate B

    24. Cholinesalicylate

    25. Ethanaminium, 2-hydroxy-n,n,n-trimethyl-, 2-hydroxybenzoate (1:1)

    26. Cholini Salicylas

    27. Salicilato De Colina

    28. Cholini Salicylas [inn-latin]

    29. Salicylate De Choline

    30. Salicilato De Colina [inn-spanish]

    31. Salicylate De Choline [inn-french]

    32. Einecs 217-948-8

    33. Unii-kd510k1iqw

    34. Choline Salicylate [usan:inn:ban:jan]

    35. Arthropan (tn)

    36. Choline Salicylate (salt)

    37. Schembl3960

    38. Chebi:3668

    39. Choline Salicylate [mi]

    40. Chembl2104095

    41. Choline Salicylate [inn]

    42. Choline Salicylate [jan]

    43. Dtxsid8062103

    44. Choline Salicylate [usan]

    45. Choline Salicylate [vandf]

    46. Choline Salicylate [mart.]

    47. Choline Salicylate [who-dd]

    48. Choline Salicylate (jan/usan/inn)

    49. Mfcd00242760

    50. Akos030228339

    51. Db14006

    52. As-66082

    53. Cs-0449641

    54. D00810

    55. (2-hydroxyethyl)trimethylazanium 2-hydroxybenzoate

    56. A909239

    57. (2-hydroxyethyl)trimethyl Ammonium Salicylate

    58. 2-carboxyphenolate,2-hydroxyethyl(trimethyl)azanium

    59. Q4499058

    60. (2-hydroxyethyl)trimethylammonium 2-hydroxybenzoate

    61. 2-hydroxy-n,n,n-trimethylethan-1-aminium 2-hydroxybenzoate

    62. 2-hydroxy-n,n,n-trimethylethan-1-aminium 2-carboxyphenolate

    63. Benzoic Acid, 2-hydroxy-, Ion(1-), 2-hydroxy-n,n,n-trimethylethanaminium

    2.4 Create Date
    2011-12-26
    3 Chemical and Physical Properties
    Molecular Weight 241.28 g/mol
    Molecular Formula C12H19NO4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count3
    Exact Mass241.13140809 g/mol
    Monoisotopic Mass241.13140809 g/mol
    Topological Polar Surface Area80.6 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity179
    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 Drug Indication

    The oral gel is indicated for the relief of pain and discomfort of common mouth ulcers, cold sores, denture sore spots, infant teething and mouth ulcers, and sore spots due to orthodontic devices in children.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    This is an anti-inflammatory and antipyretic medication,. If is often used in oral gel form for the relief of pain, discomfort, and inflammation caused by common mouth ulcers, cold sores, denture and sore spots, as well as mouth ulcers, and sore spots because of orthodontic devices.

    5.2 ATC Code

    N - Nervous system

    N02 - Analgesics

    N02B - Other analgesics and antipyretics

    N02BA - Salicylic acid and derivatives

    N02BA03 - Choline salicylate

    5.3 Absorption, Distribution and Excretion

    Absorption

    Onset: 1-2 hr after ingestion In the oral form, choline salicylate is absorbed across the buccal mucosa. There is a need for caution not to exceed the stated dose and monitor for any signs of suggested salicylism, especially when this drug is used for infants. In one study, it was found that this drug was more rapidly absorbed than ASA (absorption t1/2 = 0.1 vs 0.36 h).

    Route of Elimination

    Both metabolites of choline salicylate, and a small amount of intact salicylic acid are excreted, primarily in the urine.

    Volume of Distribution

    0.15 L/kg (salicylate), and widely distributed throughout extracellular water and most tissues

    5.4 Metabolism/Metabolites

    The metabolism of salicylic acid is by glycine and phenolic or acyl glucuronate conjugation with small amounts of the drug undergoing hydroxylation. Extensively metabolized in the liver; inactive metabolites are excreted by the kidneys.

    5.5 Biological Half-Life

    The plasma half-life of salicylic acid is 2-4 hours. Up to 15 30 h with larger doses due to saturation of liver metabolism capacity.

    5.6 Mechanism of Action

    Choline salicylate relieves pain by inhibition of prostaglandin synthesis and reduces fever by acting on the hypothalamus heat-regulating center. It also inhibits the generation of impulses through the inhibition of cyclooxygenase enzyme (COX),. Cyclooxygenase is involved in the production of prostaglandins, in response to injury and after various other stimuli. The prostaglandins promote pain, swelling, and inflammation. The choline salicylate decreases inflammation and pain by reducing the production of these prostaglandins in the area of the mouth it is applied to.

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