Salicylsalicylic acid

• CAS No:

552-94-3

• Formula:

C14H10O5

• Chemical Name:

Salicylsalicylic acid

Description

Salsalate is a nonsteroidal anti-inflammatory drug (NSAID).Target ：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. Common conditions in which Salsalate may be indicated include inflammatory disorders.

Salsalate is a dimeric benzoate ester obtained by intermolecular condensation between the carboxy of one molecule of salicylic acid with the phenol group of a second. It is a prodrug for salycylic acid that is used for treatment of rheumatoid arthritis and osteoarthritis and also shows activity against type II diabetes. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antirheumatic drug, a hypoglycemic agent, an antineoplastic agent, an EC 3.5.2.6 (beta-lactamase) inhibitor and a prodrug. It is a benzoate ester, a member of benzoic acids, a member of phenols and a member of salicylates. It derives from a salicylic acid.|Salsalate is a nonsteroidal anti-inflammatory agent for oral administration. Salsalate's mode of action as an anti-inflammatory and antirheumatic agent may be due to inhibition of synthesis and release of prostaglandins. The usefulness of salicylic acid, the active in vivo product of salsalate, in the treatment of arthritic disorders has been established. In contrast to aspirin, salsalate causes no greater fecal gastrointestinal blood loss than placebo. Salsalate is readily soluble in the small intestine where it is partially hydrolyzed to two molecules of salicylic acid. A significant portion of the parent compound is absorbed unchanged and undergoes rapid esterase hydrolysis in the body. The parent compound has an elimination half-life of about 1 hour. Salicylic acid (the active metabolite) biotransformation is saturated at anti-inflammatory doses of salsalate. Such capacity limited biotransformation results in an increase in the half-life of salicylic acid from 3.5 to 16 or more hours.|Salsalate is a nonacetylated dimer of salicylic acid that is used in the treatment of chronic arthritis as an analgesic and antipyretic. Salsalate can cause moderate serum aminotransferase elevations when given in high doses in a manner similar to aspirin.|Salsalate is an orally available salicylate and non-steroidal anti-inflammatory drug (NSAID), with anti-inflammatory, analgesic and antipyretic activities. As a prodrug, salsalate is hydrolyzed to salicylic acid which inhibits the expression of cyclooxygenase (COX) enzymes. This prevents the conversion of arachidonic acid into prostaglandin precursors and leads to decreased formation of prostaglandins that are involved in pain, fever and inflammation. In addition, salsalate appears to inhibit nuclear factor-kappa B (NF-kB), thereby preventing activation of the NF-kB-mediated pathway and the expression of genes involved in inflammation.

Salicylsalicylic acid Basic Attributes

Molecular Weight ：258.23

Exact Mass ：258.23

EC Number ：209-027-4

UNII ：V9MO595C9I

NSC Number ：755823|49171

DSSTox ID ：DTXSID1023572

NCI Thesaurus Code ：C62636

ATC Code ：N - Nervous system

Characteristics

PSA ：83.8

XLogP3 ：3

Appearance ：white to tan Crystalline Powder

Density ：1.4±0.1 g/cm3

Melting Point ：147 °C

Boiling Point ：482.9°C at 760 mmHg

Flash Point ：188.0±16.7 °C

Refractive Index ：1.646

Water Solubility ：HYDROLYSIS;DMSO: ≥15mg/mL

Storage Conditions ：room temp

Collision Cross Section ：151.3 Å ² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Salicylsalicylic acid Use

Nonacetylated (e.g., sodium salicylate) and acetylated (aspirin) forms of salicylate are widely used to target inflammation in the treatment of insulin resistance, type 2 diabetes, or rheumatic pain. Salsalate is a 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. Proof-of-principle clinical studies demonstrate that 3-4.5 g/d salsalate can reduce blood glucose, triglyceride, free fatty acid and C-reactive protein concentrations, improve glucose utilization, and increase 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.