Salsalate
Clinical data
Trade namesDisalcid, Salflex
AHFS/Drugs.comMonograph
MedlinePlusa682880
ATC code
Legal status
Legal status
Identifiers
  • 2-(2-Hydroxybenzoyl)oxybenzoic acid
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 mass258.229 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.[2]

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.[3]

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.[3][4][5] This mechanism is thought to be responsible for salsalate's insulin-sensitizing and blood sugar lowering properties.[4]

Medical uses

Salsalate may be used for inflammatory disorders such as rheumatoid arthritis or noninflammatory disorders such as osteoarthritis.[3][6]

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.[4]

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.[3] However, the use of salsalate to prevent the progression from prediabetes to type 2 diabetes mellitus has received limited study.[3]

History

This section is missing information about first known synthesis and commercialization — who decided to stick two salicylic acid molecules together?. Please expand the section to include this information. Further details may exist on the talk page. (January 2023)

Salsalate had been suggested as possible treatment for diabetes as early as 1876.[3][7][8]

Synthesis

Salsalate synthesis:[9][10][11][12]

References

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ "Salsalate". drugs.com.
  3. ^ 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". American Health & Drug Benefits. 7 (4): 231–5. PMC 4105730. PMID 25126374.
  4. ^ 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 Opinion on Investigational Drugs (Review). 24 (3): 283–307. doi:10.1517/13543784.2015.974804. PMID 25345753. S2CID 23674166.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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. S2CID 28974642.
  8. ^ Ebstein W (1876). "Zur therapie des diabetes mellitus, insbesondere uber die anwendung des salicylsauren natron bei demselben". Berliner Klinische Wochenschrift. 13: 337–340.
  9. ^ Cavallito CJ, Buck JS (1943). "Synthesis of Phenolic Acid Esters. I. Depsides1". Journal of the American Chemical Society. 65 (11): 2140–2142. doi:10.1021/ja01251a034.
  10. ^ 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.
  11. ^ 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 
  12. ^ 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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