A metabolite of 5-ASA and sulfasalazine
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N-acetyl-5-Aminosalicylic Acid

Item No. 27618

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-(acetylamino)-2-hydroxy-benzoic acid
CAS Number
51-59-2
Synonyms
  • Acetylmesalazine
  • N-acetyl-ASA
  • N-acetyl Mesalamine
  • NSC 54183
  • Salicytamide
Molecular Formula
C9H9NO4
Formula Weight
195.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleMethanol: slightly soluble
SMILES
OC1=C(C(O)=O)C=C(NC(C)=O)C=C1
InChi Code
InChI=1S/C9H9NO4/c1-5(11)10-6-2-3-8(12)7(4-6)9(13)14/h2-4,12H,1H3,(H,10,11)(H,13,14)
InChi Key
GEFDRROBUCULOD-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $49

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    50 mg

    $77

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    100 mg

    $132

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    250 mg

    $283

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    Product Description

    N-acetyl-5-Aminosalicylic acid is a metabolite of the anti-inflammatory agent 5-aminosalicylic acid (5-ASA; Item No. 70265) and its prodrug form, sulfasalazine (Item No. 15025).1,2 It is formed in the liver, intestinal lumen, and colonic epithelial cells via N-acetyltransferases.3 It reduces IFN-γ binding to colonic epithelial cells by 24% when used at a concentration of 10 mM.4 N-acetyl-5-Aminosalicylic acid (100 µM) scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay and inhibits base hydroxylation in DNA stimulated by hydroxy radicals.1,5 Unlike sulfasalazine, N-acetyl-5-aminosalicylic acid does not inhibit 15-hydroxy prostaglandin dehydrogenase (PGDH).2 Urinary levels of N-acetyl-5-aminosalicylic acid have been used as a marker of 5-ASA adherence in patients with inflammatory bowel disease.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Allgayer, H., Kolb, M., Stuber, V., et al. Modulation of base hydroxylation by bile acids and salicylates in a model of human colonic mucosal DNA: Putative implications in colonic cancer. Dig. Dis. Sci. 44(4), 761-767 (1999).

    2. Berry, C.N., Hoult, J.R., Peers, S.H., et al. Inhibition of prostaglandin 15-hydroxydehydrogenase by sulphasalazine and a novel series of potent analogues. Biochem. Pharmacol. 32(19), 2863-2871 (1983).

    3. Small, R.E., and Schraa, C.C. Chemistry, pharmacology, pharmacokinetics, and clinical applications of mesalamine for the treatment of inflammatory bowel disease. Pharmacotherapy 14(4), 385-398 (1994).

    4. Crotty, B., Rosenberg, W.M., Aronson, J.K., et al. Inhibition of binding of interferon-γ to its receptor by salicylates used in inflammatory bowel disease. Gut 33(10), 1353-1357 (1992).

    5. Borges, R.S., Pereira, G.A., Vale, J.K., et al. Design and evaluation of 4-aminophenol and salicylate derivatives as free-radical scavenger. Chem. Biol. Drug Des. 81(3), 414-419 (2013).

    6. Červený, P., Bortlík, M., Kuběna, A., et al. Nonadherence in inflammatory bowel disease: Results of factor analysis. Inflamm. Bowel Dis. 13(10), 1244-1249 (2007).