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Identification
Name Trisalicylate-choline
Accession Number DB01401
Type small molecule
Groups approved
Description

Choline magnesium trisalicylate is a non-acetylated salicylate used widely as a nonsteroidal anti-inflammatory drug. Trisalicylate significantly reduces methotrexate renal clearance, displacing methotrexate from protein, increasing the fraction unbound by 28%.(PMID: 1728115, 1618240)
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories Not Available
CAS number Not Available
Weight Average: 539.814
Monoisotopic: 539.164188051
Chemical Formula C26H29MgNO10
InChI Key InChIKey=FQCQGOZEWWPOKI-UHFFFAOYSA-K
InChI
InChI=1S/3C7H6O3.C5H14NO.Mg/c3*8-6-4-2-1-3-5(6)7(9)10;1-6(2,3)4-5-7;/h3*1-4,8H,(H,9,10);7H,4-5H2,1-3H3;/q;;;+1;+2/p-3
Plain Text
IUPAC Name
magnesium(2+) ion (2-hydroxyethyl)trimethylazanium tris(2-hydroxybenzoate)
SMILES
[Mg++].C[N+](C)(C)CCO.OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Choline magnesium trisalicylate is used to reduce pain and inflammation caused by conditions such as arthritis. This medication is also used to treat fever in adults.
Pharmacodynamics Trisalicylate-choline is a non-steroidal anti-inflammatory drug (NSAID) that contains a combination of choline salicylate and magnesium salicylate. Does not affect platelet aggregation.
Mechanism of action Inhibits prostaglandin synthesis; acts on the hypothalamus heat-regulating center to reduce fever; blocks the generation of pain impulses
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination renal
Half life Not Available
Clearance Not Available
Toxicity Salicylate intoxication, known as salicylism, may occur with large doses or extended therapy. Common symptoms of salicylism include headache, dizziness, tinnitus, hearing impairment, confusion, drowsiness, sweating, vomiting, diarrhea, and hyperventilation. A more severe degree of salicylate intoxication can lead to CNS disturbances, alteration in electrolyte balance, respiratory and metabolic acidosis, hyperthermia, and dehydration.
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Choline mag trisal 1 gm tablet 1.23 USD tablet
Choline mag trisal 750 mg tablet 0.81 USD tablet
Choline mag trisal 500 mg tablet 0.57 USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
logP 1.98 ChemAxon
pKa (strongest acidic) 2.79 ChemAxon
pKa (strongest basic) -6.3 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 60.36 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 46.13 ChemAxon
polarizability 12.38 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PharmGKB PA164749164 Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Betamethasone The corticosteroid, betamethasone, may decrease the effect of the salicylate, trisalicylate-choline.
Chlorpropamide The salicylate, trisalicylate-choline, increases the effect of the sulfonylurea, chlorpropamide.
Fludrocortisone The corticosteroid, fludrocortisone, may decrease the effect of the salicylate, trisalicylate-choline.
Gliclazide The salicylate, trisalicylate-choline, increases the effect of the sulfonylurea, gliclazide.
Glyburide The salicylate, trisalicylate-choline, increases the effect of the sulfonylurea, glibenclamide.
Hydrocortisone The corticosteroid, hydrocortisone, may decrease the effect of the salicylate, trisalicylate-choline.
Methazolamide The salicylate, trisalicylate-choline, at high dose increases the effect of the carbonic anhydrase inhibitor, methazolamide.
Methotrexate The salicylate, trisalicylate-choline, increases the effect and toxicity of methotrexate.
Minocycline Formation of non-absorbable complexes
Prednisolone The corticosteroid, prednisolone, may decrease the effect of the salicylate, trisalicylate-choline.
Prednisone The corticosteroid, prednisone, may decrease the effect of the salicylate, trisalicylate-choline.
Probenecid The salicylate, trisalicylate-choline, decreases the uricosuric effect of probenecid.
Tetracycline Formation of non-absorbable complexes
Triamcinolone The corticosteroid, triamcinolone, may decrease the effect of the salicylate, trisalicylate-choline.
Warfarin The antiplatelet effects of trisalicylate-choline may increase the bleed risk associated with warfarin.
Food Interactions Not Available
Targets

1. Prostaglandin G/H synthase 1

Pharmacological action: unknown
Actions: inhibitor

May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells

Organism class: human
UniProt ID: P23219 Link_out
Gene: PTGS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Nizankowska E, Dworski R, Soja J, Szczeklik A: Salicylate pre-treatment attenuates intensity of bronchial and nasal symptoms precipitated by aspirin in aspirin-intolerant patients. Clin Exp Allergy. 1990 Nov;20(6):647-52. Pubmed
  2. Simon RA: Adverse respiratory reactions to aspirin and nonsteroidal anti-inflammatory drugs. Curr Allergy Asthma Rep. 2004 Jan;4(1):17-24. Pubmed
  3. Schwartz KA: Aspirin resistance: a review of diagnostic methodology, mechanisms, and clinical utility. Adv Clin Chem. 2006;42:81-110. Pubmed

2. Prostaglandin G/H synthase 2

Pharmacological action: unknown
Actions: inhibitor

May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity

Organism class: human
UniProt ID: P35354 Link_out
Gene: PTGS2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Simon RA: Adverse respiratory reactions to aspirin and nonsteroidal anti-inflammatory drugs. Curr Allergy Asthma Rep. 2004 Jan;4(1):17-24. Pubmed
  2. Brzozowski T, Konturek PC, Sliwowski Z, Kwiecien S, Drozdowicz D, Pawlik M, Mach K, Konturek SJ, Pawlik WW: Interaction of nonsteroidal anti – inflammatory drugs (NSAID) with Helicobacter pylori in the stomach of humans and experimental animals. J Physiol Pharmacol. 2006 Sep;57 Suppl 3:67-79. Pubmed
  3. Wang HJ, Liu XJ, Yang KX, Luo FM, Lou JY, Peng ZL: [Effects of nonsteroidal anti-inflammatory drug celecoxib on expression of cyclooxygenase-2 (COX-2) in ovarian carcinoma cell] Sichuan Da Xue Xue Bao Yi Xue Ban. 2006 Sep;37(5):757-60. Pubmed
  4. Shen J, Gammon MD, Terry MB, Teitelbaum SL, Neugut AI, Santella RM: Genetic polymorphisms in the cyclooxygenase-2 gene, use of nonsteroidal anti-inflammatory drugs, and breast cancer risk. Breast Cancer Res. 2006;8(6):R71. Pubmed
  5. Nakano M, Denda N, Matsumoto M, Kawamura M, Kawakubo Y, Hatanaka K, Hiramoto Y, Sato Y, Noshiro M, Harada Y: Interaction between cyclooxygenase (COX)-1- and COX-2-products modulates COX-2 expression in the late phase of acute inflammation. Eur J Pharmacol. 2007 Mar 22;559(2-3):210-8. Epub 2006 Dec 16. Pubmed
Comments
Drug created on July 08, 2007 11:07 / Updated on February 08, 2013 16:20