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Sulfasalazine

AOB0046

CAS 599-79-1

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Data sheet

Molecular FormulaC18H14N4O5S
Molecular Weight398.39
CAS Numbers599-79-1
Storage Condition0C Short Term, -20C Long Term
SolubilityDMSO
Purity98% by HPLC
Synonym
IUPAC/Chemical Name
InChl Key
InChl Code
SMILES CodeOC(=O)C1=CC(=CC=C1O)N=NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=CC=N1
ReferencesGadangi P, et al. J Immunol,1996, 156[5], 1937-1941.

More info

Sulfasalazine (Azulfidine) is a synthetic salicylic acid derivative with affinity for elastin-containing connective tissues and formulated as a prodrug. Sulfasalazine induces iron death and inhibits NF-?B, TGF-? and COX-2.

1. Pharmacological Class

  • Type: Prodrug (inactive until metabolized)

  • Metabolized into:

    • Sulfapyridine – primarily responsible for antibacterial and some systemic effects

    • 5-Aminosalicylic acid (5-ASA or mesalamine) – responsible for local anti-inflammatory effects in the gut

⚙️ 2. Mechanism of Action

Although the exact mechanism is complex and not fully understood, its main functional effects include:

a. Anti-inflammatory action

  • Inhibits cyclooxygenase (COX) and lipoxygenase pathways, reducing prostaglandin and leukotriene synthesis (key mediators of inflammation).

  • Scavenges reactive oxygen species (ROS), reducing oxidative tissue damage.

b. Immunomodulatory effects

  • Suppresses T-cell proliferation and cytokine release (e.g., TNF-α, IL-1, IL-6).

  • Inhibits NF-κB activation, a central transcription factor for inflammatory genes.

  • Reduces B-cell antibody production and natural killer (NK) cell activity.

c. Antibacterial effect (minor)

  • The sulfapyridine moiety has sulfonamide-type antibacterial activity, though not the main therapeutic goal.

3. Therapeutic Applications

Disease / ConditionFunctional Role of Sulfasalazine
Rheumatoid arthritis (RA)Slows joint damage and inflammation; considered a first-line DMARD.
Ankylosing spondylitisReduces inflammation and stiffness, especially in peripheral joints.
Ulcerative colitis (UC)Acts locally in the colon to reduce mucosal inflammation.
Crohn’s disease (colonic type)Sometimes used, though less effective than in UC.
Psoriatic arthritisHelps control synovial inflammation and pain.

4. Cellular / Molecular Research Uses

In laboratory or experimental studies, sulfasalazine is often used to:

  • Inhibit NF-κB signaling in cell culture models.

  • Induce oxidative stress resistance or modulate glutathione metabolism.

  • Study cancer cell apoptosis and autophagy, since sulfasalazine inhibits xCT (SLC7A11), a cystine/glutamate antiporter, leading to glutathione depletion and ferroptosis in tumor cells.

⚠️ 5. Notable Considerations

  • Adverse effects: Nausea, rash, headache, reversible oligospermia, hematologic effects (e.g., agranulocytosis, anemia).

  • Monitoring: CBC and liver function during therapy.

  • Folate metabolism interference: Often supplemented with folic acid.