Sulfasalazine
Sulfasalazine is a mesalazine derivative sulfa drug that exhibits anti-inflammatory, immunomodulatory, analgesic, antioxidative, neuromodulatory, and anti-fibrotic activities. Sulfasalazine is clinically used to treat rheumatoid arthritis, inflammatory bowel disease, and Crohn’s disease; in vivo, it is metabolized into 5-aminosalicylic acid. Sulfasalazine inhibits sepiapterin reductase and decreases tetrahydrobiopterin (BH4) levels in vivo. Additionally, sulfasalazine scavenges ROS and RNS in vitro and inhibits NMDA receptors, inducing receptor desensitization and decreasing channel open probability. This compound also induces apoptosis in hepatic stellate cells, decreasing levels of procollagen I and TIMP1, suppressing activation of NF-κB, increasing levels of matrix metalloproteinase 2 (MMP2), and preventing fibrosis in vivo.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18974151
| Cas No. |
599-79-1 |
|---|---|
| Purity |
≥98% |
| Formula |
C18H14N4O5S |
| Formula Wt. |
398.39 |
| Chemical Name |
2-Hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]- azo]benzoic acid |
| IUPAC Name |
(3Z)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid |
| Synonym |
Azulfidine; ColoPleon; Salazopyrin |
| Melting Point |
240-245°C(dec) |
| Solubility |
Slightly soluble in alcohol (0.3 mg/mL) and methanol (0.6 mg/mL). Practically insoluble in water, benzene, chloroform and ether. |
| Appearance |
Bright to brownish yellow powder |
Costigan M, Latremoliere A, Woolf CJ. Analgesia by inhibiting tetrahydrobiopterin synthesis. Curr Opin Pharmacol. 2012 Feb;12(1):92-9. PMID: 22178186.
Couto D, Ribeiro D, Freitas M, et al. Scavenging of reactive oxygen and nitrogen species by the prodrug sulfasalazine and its metabolites 5-aminosalicylic acid and sulfapyridine. Redox Rep. 2010;15(6):259-67. PMID: 21208525.
Noh JH, Gwag BJ, Chung JM. Underlying mechanism for NMDA receptor antagonism by the anti-inflammatory drug, sulfasalazine, in mouse cortical neurons. Neuropharmacology. 2006 Jan;50(1):1-15. PMID: 16169564.
Oakley F, Meso M, Iredale JP, et al. Inhibition of inhibitor of kappaB kinases stimulates hepatic stellate cell apoptosis and accelerated recovery from rat liver fibrosis. Gastroenterology. 2005 Jan;128(1):108-20. PMID: 15633128.
Fleischmann R. Safety and efficacy of disease-modifying antirheumatic agents in rheumatoid arthritis and juvenile rheumatoid arthritis. Expert Opin Drug Saf. 2003 Jul;2(4):347-65. PMID: 12904092.
