Salsalate

Salsalate
Names
Trade namesDisalcid, Salflex, other
Other namesSalicylsalicylic acid, sodium salicylate
IUPAC name
  • 2-(2-Hydroxybenzoyl)oxybenzoic acid
Clinical data
Drug classNSAID (salicylate)[1]
Main usesInflammation[1]
Side effectsRinging in the ears, nausea, rash, Reye syndrome, stomach bleeding, kidney problems, anaphylaxis[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • US: C (Risk not ruled out)
    Typical dose1 to 1.5 gram[1]
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa682880
    Legal
    Legal status
    Chemical and physical data
    FormulaC14H10O5
    Molar mass258.229 g·mol−1

    Salsalate, sold under the brand name Disalcid among others, is a medication used to treat inflammation in conditions such as rheumatoid arthritis.[1] It is taken by mouth.[1]

    Common side effects include ringing in the ears, nausea, and rash.[1] Other side effects may include Reye syndrome, stomach bleeding, kidney problems, liver problems, and anaphylaxis.[1] Use in the later part of pregnancy may harm the baby.[1] It is a nonsteroidal anti-inflammatory drug (NSAID) of the salicylate type and blocks both COX-1 and COX-2.[1]

    Salsalate was introduced in the 1960s.[2] It is available as a generic medication.[3] In the United States 60 tablets of 750 mg costs about 25 USD as of 2021.[3]

    Medical uses

    Salsalate may be used for inflammatory disorders such as rheumatoid arthritis or noninflammatory disorders such as osteoarthritis.[4][5]

    Dosage

    The typical dose is 1,000 mg three time per day or 1,500 mg twice per day.[1]

    Side effects

    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.[6]

    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.[4]

    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.[4][6][7] This mechanism is thought to be responsible for salsalate's insulin-sensitizing and blood sugar lowering properties.[6]

    History

    Salsalate had been suggested as possible treatment for diabetes as early as 1876.[4][8][9]

    Society and culture

    Names

    Salsalate is the generic name of a prescription medication marketed under the brandnames Mono-Gesic, Salflex, Disalcid, and Salsitab. Other generic and brand name formulations may be available.[10]

    Synthesis

    Salsalate synthesis:[11][12] DE 211403  and DE 214044  (1909, both to Boehringer, Mann.), Frdl. 9, 928 and C.A. 4, 368 (1910).

    Research

    Salsalate has been proposed for the prevention and treatment of type 2 diabetes due to its ability to lower insulin resistance associated with inflammation and may be useful in prediabetes.[4] However, the use of salsalate to prevent the progression from prediabetes to type 2 diabetes mellitus has received limited study.[4]

    References

    1. 1 2 3 4 5 6 7 8 9 10 11 "Salsalate Monograph for Professionals". Drugs.com. Archived from the original on 30 January 2021. Retrieved 10 October 2021.
    2. ↑ Lane, Nancy E.; Wallace, Daniel Jeffrey (2002). All about Osteoarthritis: The Definitive Resource for Arthritis Patients and Their Families. Oxford University Press. p. 165. ISBN 978-0-19-513873-3. Archived from the original on 2021-10-11. Retrieved 2021-10-10.
    3. 1 2 "Salsalate Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 10 October 2016. Retrieved 10 October 2021.
    4. 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". American Health & Drug Benefits. 7 (4): 231–5. PMC 4105730. PMID 25126374.
    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. 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". Expert Opinion on Investigational Drugs (Review). 24 (3): 283–307. doi:10.1517/13543784.2015.974804. PMID 25345753.
    7. ↑ 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.
    8. ↑ 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.
    9. ↑ Ebstein W (1876). "Zur therapie des diabetes mellitus, insbesondere uber die anwendung des salicylsauren natron bei demselben". Berliner Klinische Wochenschrift. 13: 337–340.
    10. ↑ "drugs.com Salsalate entry". Archived from the original on 2020-12-05. Retrieved 2020-10-20.
    11. ↑ 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.
    12. ↑ 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.
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