552-94-3 Usage
Description
Salsalate, or salicylsalicylic acid, (pKa 3.5 [COOH], 9.8 [AR-OH]) is a dimer of salicylic acid. It is insoluble in gastric
juice but is soluble in the small intestine, where it is partially hydrolyzed to two molecules of salicylic acid and
absorbed. On a molar basis, it produces 15% less salicylic acid than aspirin. It does not cause GI blood loss and can
be given to aspirin-sensitive patients. Salsalate is available as capsules and tablets.
Chemical Properties
white crystalline powder
Uses
Different sources of media describe the Uses of 552-94-3 differently. You can refer to the following data:
1. Nonacetylated aspirin analog. Analgesic, anti-inflammatory.
2. 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. Sasapyrine 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.
3. Salicylsalicylic acid is used in organic synthesis and functions as a plant hormone, as a key ingredient in topical anti-acne products.
Definition
ChEBI: 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 osteoarthrit
s and also shows activity against type II diabetes.
Brand name
Disalcid (3M Pharmaceuticals).
General Description
Salsalate, salicylsalicylic acid (Amigesic, Disalcid,Salflex), is the ester formed between two salicylic acidmolecules. It is rapidly hydrolyzed to salicylic acid followingits absorption. It reportedly causes less gastric irritationthan aspirin, because it is relatively insoluble inthe stomach and is not absorbed until it reaches the smallintestine.
Biochem/physiol Actions
Salsalate is a nonsteroidal anti-inflammatory drug (NSAID), a nonacetylated salicylate with no more problems of gastrointestinal bleeding than placebo. It inhibits synthesis and release of prostaglandins through the inactivation of cyclooxygenase-1 (COX-1) and COX-2. Salsalate is currently being investigated as a treatment for Type 2 diabetes with possible use to prevent the disease in people at risk. It reduces blood glucose concentrations in patients with type 2 diabetes, as well as in insulin-resistant patients without diabetes.
Check Digit Verification of cas no
The CAS Registry Mumber 552-94-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 2 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 552-94:
(5*5)+(4*5)+(3*2)+(2*9)+(1*4)=73
73 % 10 = 3
So 552-94-3 is a valid CAS Registry Number.
InChI:InChI=1/C14H10O5/c15-11-7-3-1-5-9(11)14(18)19-12-8-4-2-6-10(12)13(16)17/h1-8,15H,(H,16,17)/p-1
552-94-3Relevant articles and documents
Disalicylate synthesis process
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Paragraph 0026-0031, (2020/08/02)
The invention discloses a novel environment-friendly disalicylate synthesis process. The process comprises the following steps: taking salicylic acid as a raw material and an organic solvent as a solvent, dissolving the salicylic acid in the organic solvent at normal pressure, dropwise adding diethylamine to form salicylic acid diethylamine salt, performing condensation reaction by utilizing polyphosphoric acid to generate a mixture of disalicylate and diethylamine phosphate, distilling off the organic solvent, adding water for hydrolysis to obtain water-insoluble disalicylate and a diethylamine phosphate solution, and neutralizing the diethylamine phosphate solution with an alkali to easily obtain trisodium phosphate crystals and diethylamine, so that no sodium chloride solid waste is generated. The yield is more than 95%, and the purity is more than or equal to 99% (HPLC). Compared with a traditional process, phosphorus trichloride or phosphorus oxychloride is not used, the obtainedtrisodium phosphate can be used for producing sodium hexametaphosphate, the production efficiency is greatly high, the cost is low, and industrial production is easy.
Evaluation of glycolamide esters and various other esters of aspirin as true aspirin prodrugs
Nielsen,Bundgaard
, p. 727 - 734 (2007/10/02)
A series of glycolamide, glycolate, (acyloxy)methyl, alkyl, and aryl esters of acetylsalicylic acid (aspirin) were synthesized and evaluated as potential prodrug forms of aspirin. N,N-Disubstituted glycolamide esters were found to be rapidly hydrolized in human plasma, resulting in the formation of aspirin as well as the corresponding salicylate esters. These in turn hydrolyzed rapidly to salicylic acid. The largest amount of aspirin formed from the esters were 50 and 55% in case of the N,N-dimethyl- and N,N-diethylglycolamide esters, respectively. Similar results were obtained in blood with the N,N-dimethyl- and N,N-diethylglycolamide esters. Unsubstituted and monosubstituted glycolamide esters as well as most other esters previously suggested to be aspirin prodrugs were shown to hydrolyze exclusively to the corresponding salicylic acid esters. Lipophilicity parameters and water solubilities of the esters were determined, and structural factors favoring ester prodrug hydrolysis at the expense of deacetylation to yield salicylate ester are discussed. The properties of some N,N-disubstituted glycolamide esters of aspirin are highlighted with respect to their use as potential aspirin prodrugs.
Thermal decomposition of aspirin: Formation of linear oligomeric salicylate esters
Reepmeyer
, p. 322 - 323 (2007/10/02)
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