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03830_FLUKA

03830_FLUKA

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

3 API Suppliers, 1 CEP/COS, 2 Listed Suppliers

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Suppliers, 3 Nanjing Well Pharmaceutical, 3 BASF, 2 Seppic, 2 Actylis, 2 Gangwal Chemicals, 1 Microlex e.U, 1 Kerry

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6 Topical, 5 Solubilizers, 3 Surfactant & Foaming Agents, 3 Emulsifying Agents, 3 Parenteral, 1 Controlled & Modified Release, 1 Coating Systems & Additives

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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

03830_FLUKA

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 Formula	C₉H₁₀O₄
Molecular Weight	182.17 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	182.05790880 g/mol
Monoisotopic Mass	182.05790880 g/mol
Topological Polar Surface Area	66.8 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	169
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.