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Salsalate

Salsalate
Salsalate.svg
Clinical data
Trade namesDisalcid, Salflex
AHFS/Drugs.comMonograph
MedlinePlusa682880
Pregnancy
category
  • US: C (Risk not ruled out)
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.008.208 Edit this at Wikidata
Chemical and physical data
FormulaC14H10O5
Molar mass258.23 g/mol g·mol−1
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Salsalate is a medication that belongs to the salicylate and nonsteroidal anti-inflammatory drug (NSAID) classes.

Salsalate is the generic name of a prescription drug marketed under the brandnames Mono-Gesic, Salflex, Disalcid, and Salsitab. Other generic and brand name formulations may be available.[1]

Mechanism of action

Relative to other NSAIDs, salsalate has a weak inhibitory effect on the cyclooxygenase enzyme and decreases the production of several proinflammatory chemical signals such as interleukin-6, TNF-alpha, and C-reactive protein.[2]

The mechanism through which salsalate is thought to reduce the production of these inflammatory chemical signals is through the inhibition of IκB kinase resulting in decreased action of NF-κB genes.[2][3][4] This mechanism is thought to be responsible for salsalate's insulin-sensitizing and blood sugar lowering properties.[3]

Medical uses

Salsalate may be used for inflammatory disorders such as rheumatoid arthritis or noninflammatory disorders such as osteoarthritis.[2][5]

Safety

The risk of bleeding is a common concern with use of the NSAID class of medications. However, the bleeding risk associated with salsalate is lower than that associated with aspirin use.[3]

Research

Salsalate has been proposed for the prevention and treatment of type 2 diabetes mellitus due to its ability to lower insulin resistance associated with inflammation and may be useful in prediabetes.[2] However, the use of salsalate to prevent the progression from prediabetes to type 2 diabetes mellitus has received limited study.[2]

History

Salsalate had been suggested as possible treatment for diabetes as early as 1876.[2][6][7]

Synthesis

Salsalate synthesis:[8][9] DE 211403  and DE 214044  (1909, both to Boehringer, Mann.), Frdl. 9, 928 and C.A. 4, 368 (1910).

References

  1. ^ drugs.com Salsalate entry
  2. ^ a b c d e f Anderson K, Wherle L, Park M, Nelson K, Nguyen L (June 2014). "Salsalate, an old, inexpensive drug with potential new indications: a review of the evidence from 3 recent studies". Am Health Drug Benefits. 7 (4): 231–5. PMC 4105730. PMID 25126374.CS1 maint: uses authors parameter (link)
  3. ^ a b c Esser N, Paquot N, Scheen AJ (March 2015). "Anti-inflammatory agents to treat or prevent type 2 diabetes, metabolic syndrome and cardiovascular disease". Expert Opin Investig Drugs (Review). 24 (3): 283–307. doi:10.1517/13543784.2015.974804. PMID 25345753.CS1 maint: uses authors parameter (link)
  4. ^ Ridker PM, Lüscher TF (July 2014). "Anti-inflammatory therapies for cardiovascular disease". European Heart Journal. 35 (27): 1782–91. doi:10.1093/eurheartj/ehu203. PMC 4155455. PMID 24864079.CS1 maint: uses authors parameter (link)
  5. ^ Hardie DG (July 2013). "AMPK: a target for drugs and natural products with effects on both diabetes and cancer". Diabetes. 62 (7): 2164–72. doi:10.2337/db13-0368. PMC 3712072. PMID 23801715.CS1 maint: uses authors parameter (link)
  6. ^ Powell, Kendall (May 31, 2007). "The Two Faces of Fat". Nature. 447 (7144): 525–7. doi:10.1038/447525a. PMID 17538594.
  7. ^ Ebstein, W (1876). "Zur therapie des diabetes mellitus, insbesondere uber die anwendung des salicylsauren natron bei demselben". Berliner Klinische Wochenschrift. 13: 337–340.
  8. ^ Cavallito, Chester J.; Buck, Johannes S. (1943). "Synthesis of Phenolic Acid Esters. I. Depsides1". Journal of the American Chemical Society. 65 (11): 2140. doi:10.1021/ja01251a034.
  9. ^ Baker, Wilson; Ollis, W. D.; Zealley, T. S. (1951). "42. Eight- and higher-membered ring compounds. Part II. Di-, tri-, tetra-, and hexa-salicylides". Journal of the Chemical Society (Resumed): 201. doi:10.1039/JR9510000201.