Balsalazide

Balsalazide is an anti-inflammatory drug used in the treatment of inflammatory bowel disease. It is sold under the brand names Giazo, Colazal in the US and Colazide in the UK. It is also sold in generic form in the US by several generic manufacturers.

Balsalazide
Clinical data
Trade namesColazal, Giazo
AHFS/Drugs.comMonograph
MedlinePlusa699052
Pregnancy
category
  • US: B (No risk in non-human studies)
    ATC code
    Legal status
    Legal status
    • UK: POM (Prescription only)
    Pharmacokinetic data
    Bioavailability<1%
    Protein binding≥99%
    Elimination half-life12hr
    Identifiers
    CAS Number
    PubChem CID
    DrugBank
    ChemSpider
    UNII
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard100.117.186
    Chemical and physical data
    FormulaC17H15N3O6
    Molar mass357.322 g·mol−1
    3D model (JSmol)
     NY (what is this?)  (verify)

    It is usually administered as the disodium salt. Balsalazide releases mesalazine, also known as 5-aminosalicylic acid, or 5-ASA,[1] in the large intestine. Its advantage over that drug in the treatment of ulcerative colitis is believed to be the delivery of the active agent past the small intestine to the large intestine, the active site of ulcerative colitis.

    Synthesis

    Ex 3 is actually for Ipsalazide. See Ex 4 for Balsalazide proper. Same protocol but uses β-Alanine.

    Balsalazide synthesis: Biorex Laboratories, GB 2080796 (1986).
    1. Starting material is 4-aminohippuric acid, obtained by coupling para-aminobenzoic acid and glycine.
    2. That product is then treated with nitrous acid to give the diazonium salt.
    3. Reaction of this species with salicylic acid proceeds at the position para to the phenol to give balsalazide.
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    References
    1. Kruis W, Schreiber S, Theuer D, Brandes JW, Schütz E, Howaldt S, et al. (December 2001). "Low dose balsalazide (1.5 g twice daily) and mesalazine (0.5 g three times daily) maintained remission of ulcerative colitis but high dose balsalazide (3.0 g twice daily) was superior in preventing relapses". Gut. 49 (6): 783–9. doi:10.1136/gut.49.6.783. PMC 1728533. PMID 11709512.
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