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    Technical details about 2-Hydroxyethyl Salicylate, learn more about the structure, uses, toxicity, action, side effects and more

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    2-hydroxyethyl-salicylate

    APIs // Active Pharmaceutical Ingredients

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    2D Structure
    Also known as: 87-28-5, Glycol salicylate, 2-hydroxyethyl 2-hydroxybenzoate, Ethylene glycol monosalicylate, Espirosal, Glycol monosalicylate
    Molecular Formula
    C9H10O4
    Molecular Weight
    182.17  g/mol
    InChI Key
    LVYLCBNXHHHPSB-UHFFFAOYSA-N
    FDA UNII
    3I1VBB7AXH
    Glycol salicylate, also known as 2-hydroxyethyl salicylate, is a benzoate ester formed from the condensation of the carboxy group of salicylic acid with one of the hydroxy groups of ethylene glycol. It is found as an active ingredient and topical analgesic in patches used to provide relief for mild to moderate muscle and joint pain. This drug belongs to the salicylate group of drugs, which are used as analgesic agents for the treatment of mild to moderate pain. Glycol salicylate (GS), composed of salicylic acid (SA) and ethylene glycol, is a non-steroidal anti-inflammatory drug. This ingredient is an important component of many topical creams and sprays for the relief of aches, pains, and stiffness of the muscles, joints, and tendons.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-hydroxyethyl 2-hydroxybenzoate
    2.1.2 InChI
    InChI=1S/C9H10O4/c10-5-6-13-9(12)7-3-1-2-4-8(7)11/h1-4,10-11H,5-6H2
    2.1.3 InChI Key
    LVYLCBNXHHHPSB-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC=C(C(=C1)C(=O)OCCO)O
    2.2 Other Identifiers
    2.2.1 UNII
    3I1VBB7AXH
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ethyleneglycolmonosalicylic Acid Ester

    2. Glycol Monosalicylate

    3. Glycol Salicylate

    4. Hydroxyethyl Salicylate

    5. Menthoneurin

    2.3.2 Depositor-Supplied Synonyms

    1. 87-28-5

    2. Glycol Salicylate

    3. 2-hydroxyethyl 2-hydroxybenzoate

    4. Ethylene Glycol Monosalicylate

    5. Espirosal

    6. Glycol Monosalicylate

    7. Rheumacyl

    8. Sarocol

    9. Spirosal

    10. Glysal

    11. Ethylene Glycol Salicylate

    12. Phlogont

    13. Monoglycol Salicylate

    14. Gl 7

    15. Benzoic Acid, 2-hydroxy-, 2-hydroxyethyl Ester

    16. Glykolsalicylat

    17. Traumasenex

    18. Ethylene Glycol, Salicylate

    19. Kytta-gel

    20. Ethylene Glycol, Monosalicylate

    21. 1,2-ethylene Glycol Monosalicylate

    22. Aethylenglykolsalicylat

    23. Hydroxyethyl Salicylate

    24. 2-hydroxybenzoic Acid 2-hydroxyethyl Ester

    25. Salicylic Acid, 2-hydroxyethyl Ester

    26. Ethylenglycol-monosalicylsaeureester

    27. Nsc-72097

    28. 3i1vbb7axh

    29. .beta.-hydroxyethyl Salicylate

    30. Chebi:86541

    31. 2-hydroxyethyl 2-oxidanylbenzoate

    32. Mfcd00002862

    33. Ncgc00159379-03

    34. 2-hydroxybenzoic Acid, 2-hydroxyethyl Ester

    35. Glycol Salicylate (jan)

    36. Glycol Salicylate [jan]

    37. Unii-3i1vbb7axh

    38. Norgesic (tn)

    39. Phlogont (tn)

    40. Einecs 201-737-2

    41. Nsc 72097

    42. Ai3-05033

    43. 2-hydroxyethyl-salicylate

    44. Bmse000750

    45. Dsstox_cid_28913

    46. Dsstox_rid_83181

    47. Dsstox_gsid_48987

    48. Schembl15402

    49. Salicylic Acid Ethylene Glycol

    50. Glycol Salicylate [mi]

    51. Chembl173562

    52. Dtxsid4048987

    53. Glycol Salicylate [inci]

    54. Lvylcbnxhhhpsb-uhfffaoysa-

    55. Glycol Salicylate [mart.]

    56. Glycol Salicylate [who-dd]

    57. Cs-b1707

    58. Hy-b2208

    59. Nsc72097

    60. Zinc1698306

    61. Salicylic Acid 2-hydroxyethyl Ester

    62. Tox21_113462

    63. Akos009075810

    64. Db11323

    65. Cas-87-28-5

    66. Ncgc00159379-02

    67. Ncgc00159379-04

    68. 2-hydroxy-benzoicacid2-hydroxyethyl Ester

    69. Sy032913

    70. E0113

    71. Ft-0626298

    72. Salicylic Acid, 2-hydroxyethyl Ester (8ci)

    73. Hydroxyethyl Salicylate [ep Monograph]

    74. D01557

    75. E78954

    76. Ethylene Glycol Monosalicylate, >=98.0% (gc)

    77. A842078

    78. Q117422

    79. Sr-01000944719

    80. Sr-01000944719-1

    81. W-104034

    82. Hydroxyethyl Salicylate, European Pharmacopoeia (ep) Reference Standard

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 182.17 g/mol
    Molecular Formula C9H10O4
    XLogP31.9
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass182.05790880 g/mol
    Monoisotopic Mass182.05790880 g/mol
    Topological Polar Surface Area66.8 Ų
    Heavy Atom Count13
    Formal Charge0
    Complexity169
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    This drug is only recommended for topical usages for the relief of muscular and rheumatic pain in human and animals.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Temporarily relieves minor to moderate aches and pains. Works with ingredients such as menthol, which has counter-irritant properties. Counter-irritants are externally applied, and lead to irritation or mild inflammation of the skin to relieve pain in muscles or joints by reducing inflammation in deeper adjacent structures. Counter-irritants relieve pain by disrupting the brain from receiving pain signals resulting from conditions such as osteoarthritis (OA) or injuries such as sprains or strains. These agents may cause vasodilatation or skin irritation, leading to a false sensation of heat or warmth.

    5.2 Absorption, Distribution and Excretion

    Absorption

    Salicylate absorption follows first-order kinetics with an absorption half-life ranging from 5 to 16 minutes.

    Route of Elimination

    Salicylates are generally excreted.

    5.3 Metabolism/Metabolites

    The metabolism of glycol salicylate is similar to that of [DB00945] at other salicylates. Metabolism of salicylic acid occurs through glucuronide formation (to produce salicyl acyl glucuronide and salicyl phenolic glucuronide), conjugation with glycine (to produce salicyluric acid), and oxidation to gentisic acid. The rate of formation of salicyl phenolic glucuronide and salicyluric acid are readily saturated at low salicylic acid concentrations and their formation is described by Michaelis-Menten kinetics. The larger the dose administered, the longer it will take to reach steady-state concentrations of salicylates. There is also evidence that enzyme induction of salicyluric acid formation occurs during the metabolism of salicylates.

    5.4 Biological Half-Life

    The serum half-life of [DB00945], a similar salicylate, is 20 min.

    5.5 Mechanism of Action

    Similar to other salicylates. Salicylates and other analgesics and anti-inflammatory drugs, particularly the non-steroidal anti-inflammatory drugs (NSAID) mainly used in rheumatology, inhibit cyclooxygenase, therefore reducing prostaglandin synthesis.

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