Salsalate

Salsalate
Clinical data
Trade names Disalcid, Salflex
AHFS/Drugs.com Monograph
MedlinePlus a682880
Pregnancy
category
  • US: C (Risk not ruled out)
ATC code N02BA06 (WHO)
Legal status
Legal status
Identifiers
CAS Number 552-94-3 YesY
PubChem (CID) 5161
DrugBank DB01399 YesY
ChemSpider 4977 N
UNII V9MO595C9I YesY
KEGG D00428 N
ChEBI CHEBI:9014 N
Chemical and physical data
Formula C14H10O5
Molar mass 258.23 g/mol
 NYesY (what is this?)  (verify)

Salsalate is a medication that belongs to the salicylate and non-steroidal anti-inflammatory drug (NSAID) classes. 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.[1] 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.[1][2][3] This mechanism is thought to be responsible for salsalate's insulin-sensitizing and blood sugar lowering properties.[2] 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.[4]

Medical uses

Salsalate may be used for inflammatory disorders such as rheumatoid arthritis or noninflammatory disorders such as osteoarthritis.[1][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.[2]

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.[1] However, the use of salsalate to prevent the progression from prediabetes to type 2 diabetes mellitus has received limited study.[1]

History

Salsalate had been suggested as possible treatment for diabetes as early as 1876.[1][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. 1 2 3 4 5 6 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 4105730Freely accessible. PMID 25126374.
  2. 1 2 3 Esser N, Paquot N, Scheen AJ (March 2015). "Anti-inflammatory agents to treat or prevent type 2 diabetes, metabolic syndrome and cardiovascular disease". Exp Opin Investig Drugs (Review). 24 (3): 283–307. doi:10.1517/13543784.2015.974804. PMID 25345753.
  3. Ridker PM, Lüscher TF (July 2014). "Anti-inflammatory therapies for cardiovascular disease". Eur Heart Journal. 35 (27): 1782–91. doi:10.1093/eurheartj/ehu203. PMC 4155455Freely accessible. PMID 24864079.
  4. drugs.com Salsalate entry
  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 3712072Freely accessible. PMID 23801715.
  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.


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