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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
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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]

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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