Balsalazide

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Balsalazide
File:Balsalazide structure.svg
Clinical data
Trade namesColazal, Giazo
AHFS/Drugs.comMonograph
MedlinePlusa699052
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability<1%
Protein binding≥99%
Elimination half-life12hr
Identifiers
  • (E)-5-{[4-(2-carboxyethylcarbamoyl)phenyl]diazenyl}-2-hydroxybenzoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC17H15N3O6
Molar mass357.322 g·mol−1
3D model (JSmol)
  • O=C(O)c1cc(ccc1O)/N=N/c2ccc(cc2)C(=O)NCCC(O)=O
  • InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+ checkY
  • Key:IPOKCKJONYRRHP-FMQUCBEESA-N checkY
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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 is a prodrug of mesalazine, also known as 5-aminosalicylic acid, or 5-ASA. The advantage of balsalazide over mesalazine in the treatment of ulcerative colitis is believed to be due to balsalazide not being metabolized in the small intestine; it can thus reach the large intestine intact, where it is then metabolized to mesalazine.[2] It is in the category of disease-modifying antirheumatic drugs (DMARDs) family of medications.[3] It is unclear exactly how it works.[3]

Synthesis

[edit | edit source]

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

File:Balsalazide synthesis.png
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

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