Salsalate
Systematic (IUPAC) name
2-(2-Hydroxybenzoyl)oxybenzoic acid
Clinical data
Trade names Disalcid, Salflex
AHFS/Drugs.com
MedlinePlus
Pregnancy cat.
Legal status
Identifiers
CAS number  YesY
ATC code N02
PubChem
DrugBank
ChemSpider  N
UNII  YesY
KEGG  N
ChEBI  N
Chemical data
Formula C14H10O5 
Mol. mass 258.23 g/mol
 N   

Salsalate is a medication that belongs to the salicylate and non-steroidal anti-inflammatory drug (NSAID) classes. Relative to other NSAIDs, salsalate has a weak inhibitory effect on the cyclooxygenase enzyme and decreases the production of several pro inflammatory chemical signals such as interleukin-6, TNF-alpha, and C-reactive protein.[1] Common conditions in which salsalate may be indicated include inflammatory disorders such as rheumatoid arthritis or noninflammatory disorders such as osteoarthritis. 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]

Typical use

Salsalate is used to reduce pain and inflammation caused by conditions such as rheumatoid arthritis, osteoarthritis, and related rheumatic conditions. Salsalate is also recommended by physicians as an anti-inflammatory alternative to naproxen, and ibuprofen for patients that have had minor stomach bleeding or stomach upset. It has also been used as an alternative to narcotic pain medicine for people with spinal disc protrusion.

"In contrast to aspirin, salsalate causes no greater fecal gastrointestinal blood loss than placebo." [3]

Diabetes Mellitus Research

Salsalate has been proposed as a useful medication in the prevention or treatment of type 2 diabetes mellitus due to its ability to lower insulin resistance and may be useful in prediabetes.[1] Salsalate had been suggested as possible treatment for diabetes as early as 1876.[1][4][5] The anti-inflammatory property of salsalate may reverse the chronic inflammation thought to be the cause of diabetes in the obese.[4] However, the efficacy of salsalate to prevent the progression from prediabetes to type 2 diabetes mellitus has only been examined in a few studies.[1]

On March 20, 2010, The Joslin Diabetes Center, Boston, MA, released a report entitled: Generic Drug for Type 2 Diabetes Passes Next Clinical Hurdle - "Salsalate, an anti-inflammatory agent, shows encouraging results in preliminary trial"[6]

Synthesis

Salsalate is an example of a Depside.

Salsalate synthesis:[7]

References

  1. ^ a b c d 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". Am Health Drug Benefits 7 (4): 231–5.  
  2. ^ drugs.com Salsalate entry
  3. ^ DrugBank: DB01399 (Salsalate)
  4. ^ a b Kendall Powell (May 31, 2007). "The Two Faces of Fat". Nature 447 (7144): 525–7.  
  5. ^ Ebstein, W (1876). "Zur therapie des diabetes mellitus, insbesondere uber die anwendung des salicylsauren natron bei demselben". Berliner Klinische Wochenschrift 13: 337–340. 
  6. ^ Generic Drug for Type 2 Diabetes Passes Next Clinical Hurdle
  7. ^ Cavallito, Chester J. (1943). "Synthesis of Phenolic Acid Esters. I. Depsides 1". Journal of the American Chemical Society 65 (11): 2140–2142.