Salsalate

Salsalate is a medication that belongs to the salicylate and nonsteroidal anti-inflammatory drug (NSAID) classes.

Salsalate
Clinical data
Trade namesDisalcid, Salflex
AHFS/Drugs.comMonograph
MedlinePlusa682880
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • 2-(2-Hydroxybenzoyl)oxybenzoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.008.208
Chemical and physical data
FormulaC14H10O5
Molar mass258.229 g·mol−1
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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][10][11]

References
  1. drugs.com Salsalate entry
  2. 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". American Health & Drug Benefits. 7 (4): 231–5. PMC 4105730. PMID 25126374.
  3. Esser N, Paquot N, Scheen AJ (March 2015). "Anti-inflammatory agents to treat or prevent type 2 diabetes, metabolic syndrome and cardiovascular disease". Expert Opinion on Investigational Drugs (Review). 24 (3): 283–307. doi:10.1517/13543784.2015.974804. PMID 25345753.
  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.
  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.
  6. Powell K (May 2007). "Obesity: the two faces of fat". Nature. 447 (7144): 525–7. Bibcode:2007Natur.447..525P. 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 CJ, Buck JS (1943). "Synthesis of Phenolic Acid Esters. I. Depsides1". Journal of the American Chemical Society. 65 (11): 2140. doi:10.1021/ja01251a034.
  9. Baker W, Ollis WD, Zealley TS (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.
  10. DE 211403, "Verfarhen zur Darstellung einer kristallisierten Salicylosalicylsäure aus Salicylsäure oder ihrne Salzen [Process for preparing a crystallized salicylosalicylic acid from salicylic acid or its salts]", published 1909-06-25, assigned to C.F. Boehringer & Söhne
  11. DE 214044, "Verfarhen zur Darstellung einer kristallisierten Salicylosalicylsäure [Process for preparing a crystallized salicylosalicylic acid]", published 1909-09-20, assigned to C.F. Boehringer & Söhne
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