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045269 Salsalate (NSC 49171) CAS: 552-94-3

Specifications
References
CAS Number
552-94-3
Grade
Highly Purified
Molecular Formula
C₁₄H₁₀O₅
Molecular Weight
258.23
EU Commodity Code
38220090
UN DOT Shipping
UN3077 PGIII
Shipping Temp
Blue Ice
Storage Temp
-20°C
Salicylsalicylic acid, NSC 49171, BRN 2590908, 2-Hydroxy-2-carboxyphenyl ester-benzoic acid

Nonacetylated salicylate. Non-steroidal anti-inflammatory drug (NSAID). Reduces pain and inflammation caused by conditions such as rheumatoid arthritis, osteoarthritis and related rheumatic conditions. Prostaglandin synthesis inhibitor in vivo. Inactivates cyclooxygenase-1 (COX-1) and -2 (COX-2). IKKbeta/NF-kappaB inhibitor (at significantly higher concentrations than required for COX inhibition). Used to target inflammation in the treatment of insulin resistance, type 2 diabetes, or rheumatic pain.

Salsalate reduces blood glucose concentrations in patients with type 2 diabetes, as well as in insulin-resistant patients without diabetes. Reduces blood glucose, triglyceride, free fatty acid and C-reactive protein concentrations, improves glucose utilization and increases circulating insulin and adiponectin concentrations in obese adults at risk for the development of type 2 diabetes as well as for patients with type 2 diabetes. Dimeric prodrug comprising two esterified salicylate moieties. It is advantageous over sodium salicylate because it is insoluble at the acid pH of the stomach and passes suspended but undissolved into the small intestine, sparing the gastric mucosa direct contact.
Synonyms
Salicylsalicylic acid, NSC 49171, BRN 2590908, 2-Hydroxy-2-carboxyphenyl ester-benzoic acid
CAS No
552-94-3
Molecular Formula
C₁₄H₁₀O₅
Molecular Weight
258.23
Appearance
Supplied as a white to off-white powder.
Purity
≥98%
Storage and Stability
May be stored at RT for short-term only. Long-term storage is recommended at -20°C after receipt.
References
• Reduced risk of NSAID gastropathy (GI mucosal toxicity) with nonacetylated salicylate (salsalate): an endoscopic study: S. Roth, et al.; Semin. Arth. Rheum. 19, 11 (1990)|●Inhibition of NF-kappa B by sodium salicylate and aspirin: E. Kopp & S. Ghosh; Science 265, 956 (1994)|●Salicylates inhibit I kappa B-alpha phosphorylation, endothelial-leukocyte adhesion molecule expression, and neutrophil transmigration: J.W. Pierce, et al.; J. Immunol. 156, 3961 (1996)|●The anti-inflammatory agents aspirin and salicylate inhibit the activity of I(kappa)B kinase-beta: M.J. Yin, et al.; Nature 396, 77 (1998)|●Salsalate improves glycemia and inflammatory parameters in obese young adults: A. Fleischman, et al.; Diabetes Care 31, 289 (2008)|●Use of salsalate to target inflammation in the treatment of insulin resistance and type 2 diabetes: A.B. Goldfine, et al.; Clin. Transl. Sci. 1, 36 (2008)|●The effect of salsalate on insulin action and glucose tolerance in obese non-diabetic patients: results of a randomised double-blind placebo-controlled study: J. Koska, et al.; Diabetologia 52, 385 (2009)|●Nuclear factor-kappaB activation contributes to vascular endothelial dysfunction via oxidative stress in overweight/obese middle-aged and older humans: G.L. Pierce, et al.; Circulation 119, 1284 (2009)|●The effects of salsalate on glycemic control in patients with type 2 diabetes: A randomized trial: A.B. Goldfine, et al.; Ann. Intern. Med. 152, 346 (2010)|●Potential role of salicylates in type 2 diabetes: M.M. Rumore & K.S. Kim; Ann. Pharmacother. 44, 1207 (2010) (Review)|●Effects of salsalate therapy on recovery from vascular injury in female Zucker fatty rats: S.N. Murthy, et al.; Diabetes 59, 3240 (2010)|●Stimulation of human whole-body energy expenditure by salsalate is fueled by higher lipid oxidation under fasting conditions and by higher oxidative glucose disposal under insulin-stimulated conditions: R.C. Meex, et al.; J. Clin. Endocrinol. Metab. 96, 1415 (2011)|●Salsalate attenuates free fatty acid-induced microvascular and metabolic insulin resistance in humans: W. Chai, et al.; Diabetes Care 34, 1634 (2011)|●Modeling diabetes disease progression and salsalate intervention in Goto-Kakizaki rats: Y. Cao, et al.; J. Pharmacol. Exp. Ther. 339, 896 (2011)|●Salsalate improves glycemic control in patients with newly diagnosed type 2 diabetes: E. Faghihimani, et al.; Acta Diabetol. (Epub ahead of print) (2011)|●Salicylate downregulates 11beta-HSD1 expression in adipose tissue in obese mice and in humans, mediating insulin sensitization: M. Nixon, et al.; Diabetes 61, 790 (2012)|●The ancient drug salicylate directly activates AMP-activated protein kinase: S.A. Hawley, et al.; Science 336, 918 (2012)|●Salsalate reduces insulin resistance and plasma glucose level in persons with prediabetes: E. Faghihimani, et al.; Endocr. Pract. (Epub ahead of print) (2012)|●
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