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Choline Salicylate
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 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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