Balsalazide

Balsalazide

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Systematic (IUPAC) name
(E)-5-([4-(2-carboxyethylcarbamoyl)phenyl]diazenyl)-2-hydroxybenzoic acid
Clinical data
Trade names	Colazal, Giazo
AHFS/Drugs.com	monograph
MedlinePlus	a699052
Pregnancy category	US: B (No risk in non-human studies)
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	<1%
Protein binding	≥99%
Biological half-life	12hr
Identifiers
CAS Number	80573-04-2 Y
ATC code	A07EC04 (WHO)
PubChem	CID: 5362070
DrugBank	DB01014 Y
ChemSpider	10662422 Y
UNII	P80AL8J7ZP Y
ChEBI	CHEBI:267413 Y
ChEMBL	CHEMBL1201346 N
Chemical data
Formula	C17H15N3O6
Molecular mass	357.318 g/mol
SMILES O=C(O)c1cc(ccc1O)/N=N/c2ccc(cc2)C(=O)NCCC(O)=O
InChI 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+ Y Key:IPOKCKJONYRRHP-FMQUCBEESA-N Y
NY (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.

It is usually administered as the disodium salt. Balsalazide releases mesalazine, also known as 5-aminosalicylic acid, or 5-ASA, 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

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.