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Salsalate

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Salsalate
Clinical data
Trade namesDisalcid, Salflex
AHFS/Drugs.comMonograph
MedlinePlusa682880
ATC code
Legal status
Legal status
Identifiers
  • 2-(2-Hydroxybenzoyl)oxybenzoic acid
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard(EPA)
ECHA InfoCard100.008.208Edit this at Wikidata
Chemical and physical data
FormulaC14H10O5
Molar mass258.229 g·mol−1
 ☒NcheckY (what is this?)  (verify)

Salsalate is amedication that belongs to thesalicylate andnonsteroidal anti-inflammatory drug (NSAID) classes.

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

Mechanism of action

[edit]

Relative to other NSAIDs, salsalate has a weak inhibitory effect on thecyclooxygenase enzyme and decreases the production of several proinflammatorychemical signals such asinterleukin-6,TNF-alpha, andC-reactive protein.[2]

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

Medical uses

[edit]

Salsalate may be used for inflammatory disorders such asrheumatoid arthritis or noninflammatory disorders such asosteoarthritis.[2][5]

Safety

[edit]

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

Research

[edit]

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

History

[edit]
This sectionis 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 thetalk page.(January 2023)

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

Synthesis

[edit]
Salsalate synthesis:[8][9][10][11]

References

[edit]
  1. ^"Salsalate".drugs.com.
  2. ^abcdefAnderson 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. ^abcEsser 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.
  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.S2CID 28974642.
  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):2140–2142.Bibcode:1943JAChS..65.2140C.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 
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;withdrawn drugs;veterinary use.
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(
PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others
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