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2D Structure
Also known as: Triethanolamine salicylate, 2174-16-5, Tea-salicylate, Neo heliopan ts, Tea salicylate, Neotan w
Molecular Formula
C13H21NO6
Molecular Weight
287.31  g/mol
InChI Key
UEVAMYPIMMOEFW-UHFFFAOYSA-N
FDA UNII
H8O4040BHD

Trolamine salicylate is an organic compound or a salt formed between triethanolamine and salicylic acid. Triethanolamine neutralizes the acidity of the salicylic acid. It is a topical analgesic used for temporary relief of minor pain associated with arthritis, simple backache, muscle strains, sprains, and bruises. Unlike other topical analgesics, trolamine salicylate has no distinct odor which improves patient acceptability. It also displays low systemic absorption upon dermal or topical administration and has low skin irritant properties. As with other salicylates, trolamine salicylate is an inhibitor of cyclo-oxygenase (COX) enzymes with no reported selectivity towards a specific enzyme isoform. Trolamine salicylate serves as an active ingredient in topical over-the-counter products for temporary management of mild to moderate muscular and joint pains.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[bis(2-hydroxyethyl)amino]ethanol;2-hydroxybenzoic acid
2.1.2 InChI
InChI=1S/C7H6O3.C6H15NO3/c8-6-4-2-1-3-5(6)7(9)10;8-4-1-7(2-5-9)3-6-10/h1-4,8H,(H,9,10);8-10H,1-6H2
2.1.3 InChI Key
UEVAMYPIMMOEFW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C(=C1)C(=O)O)O.C(CO)N(CCO)CCO
2.2 Other Identifiers
2.2.1 UNII
H8O4040BHD
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Myoflex

2. Triethanolamine Salicylate

2.3.2 Depositor-Supplied Synonyms

1. Triethanolamine Salicylate

2. 2174-16-5

3. Tea-salicylate

4. Neo Heliopan Ts

5. Tea Salicylate

6. Neotan W

7. Salicylic Acid Trolamine

8. H8o4040bhd

9. 2-hydroxybenzoic Acid, Compd. With 2,2',2''-nitrilotris(ethanol) (1:1)

10. Trolamine Salicylate (usp)

11. Trolamine Salicylate [usp]

12. Benzoic Acid, 2-hydroxy-, Compd. With 2,2',2''-nitrilotris(ethanol) (1:1)

13. Arthricream

14. Myoflex

15. Sunarome W

16. Benzoic Acid, 2-hydroxy-, Compd. With 2,2',2''-nitrilotris[ethanol] (1:1)

17. Arthricream (tn)

18. Dsstox_cid_27945

19. Dsstox_rid_82697

20. Unii-h8o4040bhd

21. Dsstox_gsid_47969

22. Schembl15847

23. Salicylic Acid Triethanolamine

24. Tea-salicylate [inci]

25. Chembl2107288

26. Dtxsid4047969

27. 2-[bis(2-hydroxyethyl)amino]ethanol;2-hydroxybenzoic Acid

28. Triethanolamine, Salicylate

29. Salicylic Acid Triethanolamine Salt

30. Einecs 218-531-3

31. Tox21_201084

32. Trolamine Salicylate [mart.]

33. Trolamine Salicylate [who-dd]

34. Db11079

35. Triethanolamine Salicylate [mi]

36. Ncgc00248985-01

37. Ncgc00258636-01

38. Triethanolamine Salicylate [vandf]

39. Cas-2174-16-5

40. Trolamine Salicylate [usp Impurity]

41. Trolamine Salicylate [usp Monograph]

42. Ft-0708839

43. 2,2',2''-nitrilotriethanol 2-hydroxybenzoate

44. D08501

45. Q7845153

46. Salicylic Acid, Compound With 2,2',2''-nitrilotriethanol (1:1)

2.4 Create Date
2005-07-19
3 Chemical and Physical Properties
Molecular Weight 287.31 g/mol
Molecular Formula C13H21NO6
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Exact Mass287.13688739 g/mol
Monoisotopic Mass287.13688739 g/mol
Topological Polar Surface Area122 Ų
Heavy Atom Count20
Formal Charge0
Complexity189
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

Indicated for the temporary relief of aches, and pains of muscles and joints associated with backache, lumbago, strains, bruises, sprains and arthritic or rheumatic pain, pain of tendons and ligaments.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Trolamine salicylate is a salicylate that inhibits cyclo-oxygenase (COX) enzymes responsible for generating pro-inflammatory factors such as to induce pain and inflammation. It is thought to mediate its analgesic effect through inhibition of COX-2 enzyme, which is an induced enzyme responsible for inflammatory responses and pain in muscle and joint disorders. By inhibiting fatty acid COX enzyme, trolamine salicylate inhibits the production of prostaglandins and thromboxanes in inflammatory cells involved in generating pain and inflammation. It thereby works to temporarily reduce mild to moderate pain. In subjects with muscle soreness from exercise, administration of topical trolamine salicylate was associated with reduced duration and severity of muscule soreness compared to placebo. In subjects with osteoarthritis in hands, trolamine salicylate cream was shown to be effective in achieving temporary relief of minor pain and stiffness.


5.2 Absorption, Distribution and Excretion

Absorption

Following topical administration of 10% trolamine salicylate in healthy volunteers, salicylic acid could not be detected in serum indicating low systemic absorption.


Route of Elimination

Following topical administration of 10% trolamine salicylate in healthy volunteers, urinary recovery of total salicylate during the first 24 hours was 6.9 mg (p < 0.05), which is 1.4% of total dose.


Volume of Distribution

Topical administration of 1 gram of 10% trolamine salicylate in abdominal rat skin resulted in an approximate extravascular volume of distribution (V/F) of 24.0 mL.


5.3 Mechanism of Action

Inflammation and tissue damage in different conditions including arthritis, bursitis, joint disorder, bruises, and strains or sprains of muscle origin, induce mild to moderate pain and are associated with increase prostaglandin synthesis. This is thought to be a result of COX-2 enzyme induction. COX-2 is induced in inflammatory cells in case of cell injury, infection or activation from inflammatory cytokines such as interleukin (IL)-1 and tumor necrosis factor (TNF)-. Upon activation, COX-2 produces prostanoid mediators of inflammation such as prostaglandins and thromboxanes. Trolamine salicylate mediates its analgesic effect by inhibiting the production of inflammatory mediators that sensitize nociceptive nerve endings and generate pain.