Balsalazide

Balsalazide
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
PubChem	CID 5362070
DrugBank	DB01014^Y
ChemSpider	10662422^Y
UNII	P80AL8J7ZP^Y
ChEBI	CHEBI:267413^Y
ChEMBL	CHEMBL1201346^N
Chemical data
Formula	C₁₇H₁₅N₃O₆
Molar 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,^[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).

Starting material is 4-aminohippuric acid, obtained by coupling para-aminobenzoic acid and glycine.
That product is then treated with nitrous acid to give the diazonium salt.
Reaction of this species with salicylic acid proceeds at the position para to the phenol to give balsalazide.

References

↑ 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. doi:10.1136/gut.49.6.783. PMC 1728533. PMID 11709512.

Antidiarrheals, intestinal anti-inflammatory and anti-infective agents (A07)

Rehydration	Oral rehydration therapy

Intestinal anti-infectives	Antibiotics Amphotericin B Colistin Fidaxomicin Kanamycin Natamycin Neomycin Nystatin Paromomycin Polymyxin B Rifaximin Streptomycin Vancomycin Sulfonamides Phthalylsulfathiazole Succinylsulfathiazole Sulfaguanidine Nitrofuran Nifuroxazide Nifurzide) Imidazole Miconazole Arsenical Acetarsol Oxyquinoline Broxyquinoline

Intestinal adsorbents	Charcoal Bismuth Pectin Kaolin Crospovidone Attapulgite Diosmectite

Antipropulsives (opioids)	Opium tincture (laudanum) Codeine Morphine Camphorated opium tincture (paregoric) crosses BBB: Diphenoxylate (Diphenoxylate/atropine) Difenoxin does not cross BBB: Eluxadoline Loperamide

Intestinal anti-inflammatory agents	corticosteroids acting locally Prednisolone Hydrocortisone Prednisone Betamethasone Tixocortol Budesonide Beclometasone antiallergic agents, excluding corticosteroids Cromoglicic acid aminosalicylic acid and similar agents Sulfasalazine Mesalazine Olsalazine Balsalazide

Antidiarrheal micro-organisms	Saccharomyces boulardii

Other antidiarrheals	Albumin tannate Ceratonia Crofelemer Octreotide Racecadotril

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