Balsalazide

Last updated
Balsalazide
Balsalazide structure.svg
Clinical data
Trade names Colazal, Giazo
AHFS/Drugs.com Monograph
MedlinePlus a699052
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-life 12hr
Identifiers
  • (E)-5-{[4-(2-carboxyethylcarbamoyl)phenyl]diazenyl}-2-hydroxybenzoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.117.186 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H15N3O6
Molar mass 357.322 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+ Yes check.svgY
  • Key:IPOKCKJONYRRHP-FMQUCBEESA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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.

Contents

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

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

Balsalazide synthesis: Biorex Laboratories, .mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)} GB 2080796 (1986). 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

  1. ↑ "Colazide 750mg Capsules - Summary of Product Characteristics (SmPC)". (emc). 3 January 2019. Retrieved 2 October 2020.
  2. ↑ 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.
  3. 1 2 "Sulfasalazine". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
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