A prodrug form of 5-aminosalicylic acid
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Sulfasalazine

Item No. 15025

Technical Information
Formal Name
2-hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]diazenyl]-benzoic acid
CAS Number
599-79-1
Synonyms
  • Azopyrin
  • NSC 203730
  • NSC 667219
Molecular Formula
C18H14N4O5S
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 30 mg/mlDMSO: >100 mg/mlPBS (pH 7.2): 0.2 mg/ml
λmax
355 nm
SMILES
OC(C(C(O)=O)=C1)=CC=C1/N=N/C2=CC=C(S(NC3=CC=CC=N3)(=O)=O)C=C2
InChi Code
InChI=1S/C18H14N4O4S/c23-12-13-11-15(6-9-17(13)24)21-20-14-4-7-16(8-5-14)27(25,26)22-18-3-1-2-10-19-18/h1-12,24H,(H,19,22)/b21-20+
InChi Key
XOVOVHWJSOEKGZ-QZQOTICOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Sulfasalazine is a prodrug form of the anti-inflammatory agent 5-aminosalicylic acid (Item No. 70265) that is covalently linked to the antibiotic sulfapyridine by an azo bond.1 This bond is rapidly cleaved by bacteria in the terminal ileum and colon, releasing the active anti-inflammatory component. Sulfasalazine (0.1-5 mM) inhibits TNF-α and LPS-induced NF-κB activation in SW620 colon cancer cells.2 It also inhibits degradation of IκBα and prevents nuclear translocation of NF-κB induced by TNF-α. Sulfasalazine (0.25 mM) inhibits cystine uptake through the system xc- cysteine-glutamate transporter and inhibits the growth of U-87MG glioma cells in an NF-κB independent manner when used at concentrations ranging from 0.25 to 1 mM.3 Sulfasalazine (100 mg/kg) decreases diarrhea, increases food intake, and reverses body weight decreases in a mouse model of colitis.1 It is also suppresses antigen-induced arthritis in mice.4 Formulations containing sulfasalazine have been used in the treatment of ulcerative colitis and rheumatoid arthritis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jiang, G.L., Im, W.B., Donde, Y., et alComparison of prostaglandin E2 receptor subtype 4 agonist and sulfasalazine in mouse colitis prevention and treatment. J. Pharmacol. Exp. Ther. 335(3), 546-552 (2010).

    2. Wahl, C., Liptay, S., Adler, G., et alSulfasalazine: a Potent and Specific Inhibitor of Nuclear Factor Kappa B. J. Clin. Invest. 101 number 5, 1163-1174 (1997).

    3. Chung, W.J., and Sontheimer, H. Sulfasalazine inhibits the growth of primary brain tumors independent of nuclear factor-κB. J. Neurochem. 110(1), 182-193 (2009).

    4. Crossley, M.J., Spowage, M., and Hunneyball, I.M. Studies on the effects of pharmacological agents on antigen-induced arthritis in BALB/c mice. Drugs Exp. Clin. Res. 13(5), 273-277 (1987).

    Product Citations

    Li, Z., Ferguson, L., Deol, K.K., et alRibosome stalling during selenoprotein translation exposes a ferroptosis vulnerability. Nat. Chem. Biol. (2022).