Balsalazide

Balsalazide
Clinical data
Trade names	Colazal, Giazo
AHFS/Drugs.com	Monograph
MedlinePlus	a699052
License data	US DailyMed: by mouth;
Pregnancy; category	AU: C; ;
Routes of; administration	By mouth
ATC code	A07EC04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	<1%
Protein binding	≥99%
Elimination half-life	12hr
Identifiers
	IUPAC name (E)-5-([4-(2-carboxyethylcarbamoyl)phenyl]diazenyl)-2-hydroxybenzoic acid;
CAS Number	80573-04-2 ;
PubChem CID	5362070;
DrugBank	DB01014 ;
ChemSpider	10662422 ;
UNII	P80AL8J7ZP;
KEGG	D07488; as salt: D02715;
ChEBI	CHEBI:267413 ;
ChEMBL	ChEMBL1201346 ;
CompTox Dashboard (EPA)	DTXSID7040653 ;
ECHA InfoCard	100.117.186
Chemical and physical data
Formula	C17H15N3O6
Molar mass	357.322 g·mol−1
3D model (JSmol)	Interactive image;
	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+ ; Key:IPOKCKJONYRRHP-FMQUCBEESA-N ;
	(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,^[2] 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. 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

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

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 edit

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

External links edit

"Balsalazide". Drug Information Portal. U.S. National Library of Medicine.

[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.

[AHFS2016-3] "Sulfasalazine". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.

[1]

[2]

[3]