Balsalazide

Balsalazide

Balsalazide
Systematic (IUPAC) name
(E)-5-([4-(2-carboxyethylcarbamoyl)phenyl]diazenyl)-2-hydroxybenzoic acid
Clinical data
Trade names Colazal, Giazo
AHFS/Drugs.com
MedlinePlus
Pregnancy
category
  • US: B (No risk in non-human studies)
Legal status
Pharmacokinetic data
Bioavailability <1%
Protein binding ≥99%
Biological half-life 12hr
Identifiers
CAS Registry Number  Y
ATC code A07
PubChem CID:
DrugBank  Y
ChemSpider  Y
UNII  Y
ChEBI  Y
ChEMBL  N
Chemical data
Formula C17H15N3O6
Molecular mass 357.318 g/mol
 N   

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.

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

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.

References

  1. ^ Kruis, W.; Schreiber, I.; Theuer, D.; Brandes, J. W.; Schütz, E.; Howaldt, S.; Krakamp, B.; Hämling, J.; Mönnikes, H.; Koop, I.; Stolte, M.; Pallant, D.; Ewald, U. (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): 783–789.