5-Acetylsalicylic acid

Catalog No.S4789 Synonyms: 5-acetyl-2-hydroxybenzoic acid

For research use only.

5-Acetylsalicylic acid (5-acetyl-2-hydroxybenzoic acid) is a nonsteroidal anti-inflammatory drug.

5-Acetylsalicylic acid Chemical Structure

CAS No. 13110-96-8

Purity & Quality Control

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Biological Activity

Description 5-Acetylsalicylic acid (5-acetyl-2-hydroxybenzoic acid) is a nonsteroidal anti-inflammatory drug.
In vitro

5-Acetylsalicylic acid (5-ASA) is initially shown to downregulate the inducible cyclooxygenase/prostaglandin E2 (COX-2/PGE2) signalling in mucosa inflammatory cells. Generally 5-ASA decreases the nuclear factor κB (NF-κB) activity induced by TNF-α, modulating the NF-κB inhibitor, IκBα, as well as the NF-κB transcriptional activity induced by IL-1, although it does prevent neither IL-1-induced IκBα degradation nor IL-1-induced nuclear translocation of NF-κB family members. 5-ASA is also found to increase β-catenin expression/phosphorylation and the expression of μ-protocadherin in intestine cells while reducing the expression of Wnt/β-catenin target genes and the activity of the protein phosphatase 2A. 5-ASA enhances PPAR-γ expression/activity in intestine cells and promotes its translocation from the cytoplasm to the nucleus -- this is followed by the induction of the tumour suppressor gene PTEN, the activation of caspases 8 and 3, and the inhibition of antiapoptotic proteins. It induces membranous expression of E-cadherin and increases cell adhesion through inhibition of p-21 activated kinase-1 and modulation of N-glycosylation; Also interferes with the mitogen activated protein kinase and phosphatidylinositol-4,5-bisphosphate 3-kinase/Akt pathways[1].

In vivo 5-ASA is rapidly adsorbed and extensively acetylated to N-acetyl-5-ASA by the N-acetyltransferase 1 enzyme in intestinal epithelial cells and the liver. It is generally well tolerated and the most common side effects include headache, nausea, and abdominal pain[1].

Protocol (from reference)

Solubility (25°C)

In vitro

Chemical Information

Molecular Weight 180.16
Formula

C9H8O4

CAS No. 13110-96-8
Storage 3 years -20°C powder
2 years -80°C in solvent
Smiles CC(=O)C1=CC(=C(C=C1)O)C(=O)O

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Clinical Trial Information

NCT Number Recruitment Interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02246686 Terminated Drug: STW5-II (Iberogast N BAY98-7410)|Drug: Placebo Colitis Ulcerative Bayer November 2014 Phase 2
NCT02125292 Completed Drug: Mesalamine Healthy Shire|Takeda June 2 2014 Phase 1
NCT02077777 Completed Drug: Mesalazine Colorectal Cancer SOFAR S.p.A. October 2012 Phase 2
NCT01678300 Completed -- Ulcerative Colitis Beth Israel Deaconess Medical Center August 2012 --

(data from https://clinicaltrials.gov, updated on 2022-08-01)

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