Home Immunology & Inflammation Immunology & Inflammation related chemical 5-Acetylsalicylic acid

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5-Acetylsalicylic acid Immunology & Inflammation related chemical

Cat.No.S4789

5-Acetylsalicylic acid (5-acetyl-2-hydroxybenzoic acid) is a nonsteroidal anti-inflammatory drug.
5-Acetylsalicylic acid Immunology & Inflammation related chemical Chemical Structure

Chemical Structure

Molecular Weight: 180.16

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Quality Control

Batch: S478901 DMSO]36 mg/mL]false]]]false]]]false Purity: 99.88%
99.88

Solubility

In vitro
Batch:

DMSO : 36 mg/mL (199.82 mM)
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In vivo
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Chemical Information, Storage & Stability

Molecular Weight 180.16 Formula

C9H8O4

 Storage (From the date of receipt)
CAS No. 13110-96-8 Download SDF Storage of Stock Solutions

Synonyms 5-acetyl-2-hydroxybenzoic acid Smiles CC(=O)C1=CC(=C(C=C1)O)C(=O)O

Mechanism of Action

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.
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.
References

Clinical Trial Information

(data from https://clinicaltrials.gov, updated on 2024-05-22)

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT02246686 Terminated
Colitis Ulcerative
Bayer
 November 2014 Phase 2
NCT02125292 Completed
Healthy
Shire|Takeda
 June 2 2014 Phase 1
NCT02077777 Completed
Colorectal Cancer
SOFAR S.p.A.
 October 2012 Phase 2
NCT01678300 Completed
Ulcerative Colitis
Beth Israel Deaconess Medical Center
 August 2012 --

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