Balsalazide sodium hydrate | CAS#150399-21-6 (sodium hydrate) | Anti-inflammatory agent

MedKoo Cat#: 317308 | Name: Balsalazide sodium hydrate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Balsalazide Disodium is the disodium salt form of balsalazide, an aminosalicylate and oral prodrug that is enzymatically cleaved in the colon to produce the anti-inflammatory agent mesalazine. Mesalazine acts locally on the mucosa of the colon where it diminishes inflammation by blocking the production of arachidonic acid metabolites and other inflammatory agents. Balsalazide disodium is used to treat chronic inflammatory bowel disease.

Chemical Structure

Balsalazide sodium hydrate

CAS#150399-21-6 (sodium hydrate )

Theoretical Analysis

MedKoo Cat#: 317308

Name: Balsalazide sodium hydrate

CAS#: 150399-21-6 (sodium hydrate )

Chemical Formula: C17H17N3Na2O8

Exact Mass: 0.0000

Molecular Weight: 437.31

Elemental Analysis: C, 46.69; H, 3.92; N, 9.61; Na, 10.51; O, 29.27

Price and Availability

Size	Price	Availability
1g	USD 275.00	2 Weeks
2g	USD 450.00	2 Weeks
5g	USD 850.00	2 Weeks

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Related CAS #

80573-04-2 (free base) 150399-21-6 (sodium hydrate ) 82101-18-6 (sodium)

Synonym

Balsalazide Disodium; balsalazide; balsalazine; BX 661A; BX-661A; BX661A; Colazal; Colazide

IUPAC/Chemical Name

5-[4-(2-Carboxyethylcarbamoyl)phenylazo]salicylic Acid Disodium Salt Dihydrate

InChi Key

HYSVUPBQPCRAJM-ITFXXQIYSA-L

InChi Code

InChI=1S/C17H15N3O6.2Na.2H2O/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;;;;/h1-6,9,19H,7-8H2,(H,18,24)(H,22,23)(H,25,26);;;2*1H2/q;2*+1;;/p-2/b20-12+;;;;

SMILES Code

C1=CC(=CC=C1C(=O)NCCC(=O)[O-])NN=C2C=CC(=O)C(=C2)C(=O)[O-].O.O.[Na+].[Na+]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Balsalazide disodium suppresses colitis-associated carcinogenesis through modulation of IL-6/STAT3 pathway.

In vitro activity:

A preliminary study in cultured human colon cancer cells showed that balsalazide disodium (BSZ) inhibited colon cancer cell proliferation in vitro. Furthemore, BSZ produced a dose-dependent chemopreventive effect on colon carcinogenesis. A possible mechanism is consistent with the inhibition of cellular proliferation and the induction of apoptosis. Reference: Int J Oncol. 2000 Jul;17(1):173-9. https://www.spandidos-publications.com/ijo/17/1/173

In vivo activity:

The chemopreventive activity of BSZ was evaluated in two established animal models of colon tumorigenesis, azoxymethane-induced aberrant crypt formation in the rat and intestinal tumor formation in the B6-Min/+ mouse. Aberrant crypt foci (ACF) were induced in Fischer 344 rats via 2 subcutaneous injections of azoxymethane (20 mg/kg). BSZ was supplied in the drinking water for 8 weeks and ACF quantitated. B6-Min/+ mice were treated from 55 days of age for 90 days and intestinal tumors scored for number, size and location. BSZ treatment of AOM-injected rats reduced ACF formation in a dose-dependent manner by 60% with the greatest effect observed on ACF with 4 or more crypts. In B6-Min/+ mice a dose-dependent reduction of intestinal tumor number was observed which reached 80% in the distal small intestine and colon. Reference: Int J Oncol. 2000 Jul;17(1):173-9. https://www.spandidos-publications.com/ijo/17/1/173

	Solvent	mg/mL	mM
Solubility
	DMSO	87.0	198.94
	Water	87.0	198.94

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 437.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. MacGregor DJ, Kim YS, Sleisenger MH, Johnson LK. Chemoprevention of colon cancer carcinogenesis by balsalazide: inhibition of azoxymethane-induced aberrant crypt formation in the rat colon and intestinal tumor formation in the B6-Min/+ mouse. Int J Oncol. 2000 Jul;17(1):173-9. doi: 10.3892/ijo.17.1.173. PMID: 10853036.

In vitro protocol:

In vivo protocol:

1: Kim HY, Kim SL, Park YR, Liu YC, Seo SY, Kim SH, Kim IH, Lee SO, Lee ST, Kim SW. Balsalazide Potentiates Parthenolide-Mediated Inhibition of Nuclear Factor-κB Signaling in HCT116 Human Colorectal Cancer Cells. Intest Res. 2015 Jul;13(3):233-41. doi: 10.5217/ir.2015.13.3.233. Epub 2015 Jun 9. PubMed PMID: 26130998; PubMed Central PMCID: PMC4479738. 2: Sousa T, Yadav V, Zann V, Borde A, Abrahamsson B, Basit AW. On the colonic bacterial metabolism of azo-bonded prodrugsof 5-aminosalicylic acid. J Pharm Sci. 2014 Oct;103(10):3171-5. doi: 10.1002/jps.24103. Epub 2014 Aug 4. PubMed PMID: 25091594. 3: Dhaneshwar SS. Colon-specific prodrugs of 4-aminosalicylic acid for inflammatory bowel disease. World J Gastroenterol. 2014 Apr 7;20(13):3564-71. doi: 10.3748/wjg.v20.i13.3564. Review. PubMed PMID: 24707139; PubMed Central PMCID: PMC3974523. 4: Coman RM, Glover SC, Gjymishka A. Febrile pleuropericarditis, a potentially life-threatening adverse event of balsalazide--case report and literature review of the side effects of 5-aminosalicylates. Expert Rev Clin Immunol. 2014 May;10(5):667-75. doi: 10.1586/1744666X.2014.902313. Epub 2014 Apr 1. Review. PubMed PMID: 24689504. 5: Russo L, Schneider G, Gardiner MH, Lanes S, Streck P, Rosen S. Role of pharmacoepidemiology studies in addressing pharmacovigilance questions: a case example of pancreatitis risk among ulcerative colitis patients using mesalazine. Eur J Clin Pharmacol. 2014 Jun;70(6):709-17. doi: 10.1007/s00228-014-1660-7. Epub 2014 Mar 11. PubMed PMID: 24609467; PubMed Central PMCID: PMC4025187. 6: Sim E, Abuhammad A, Ryan A. Arylamine N-acetyltransferases: from drug metabolism and pharmacogenetics to drug discovery. Br J Pharmacol. 2014 Jun;171(11):2705-25. doi: 10.1111/bph.12598. Review. PubMed PMID: 24467436; PubMed Central PMCID: PMC4158862. 7: Sun H, Lee JJ, Papadopoulos EJ, Lee CS, Nelson RM, Sachs HC, Rodriguez WJ, Mulberg AE. Alternate endpoints and clinical outcome assessments in pediatric ulcerative colitis registration trials. J Pediatr Gastroenterol Nutr. 2014 Jan;58(1):12-7. doi: 10.1097/MPG.0000000000000186. PubMed PMID: 24121142. 8: Huang HL, Lu PL, Lin CY, Chen YH, Kuo CH, Lin WR. Klebsiella pneumoniae bacteremia and renosplenic abscesses without intestinal symptoms as the initial manifestations of non-steroidal anti-inflammatory drug-induced colitis: a rare case report. BMC Gastroenterol. 2013 Sep 22;13:139. doi: 10.1186/1471-230X-13-139. PubMed PMID: 24053429; PubMed Central PMCID: PMC3849536. 9: Sonu I, Wong R, Rothenberg ME. 5-ASA induced recurrent myopericarditis and cardiac tamponade in a patient with ulcerative colitis. Dig Dis Sci. 2013 Aug;58(8):2148-50. doi: 10.1007/s10620-013-2566-4. Epub 2013 Jan 30. PubMed PMID: 23361575. 10: Kang SM, Jang YR, Yoon HH, Kim S, Kim EY, Ha SY, Park JW. A Case of Balsalazide-Induced Limited Form of Granulomatosis with Polyangiitis with Bronchiolitis Obliterans Organizing Pneumonia-like Variant in Ulcerative Colitis. Tuberc Respir Dis (Seoul). 2012 Mar;72(3):323-7. doi: 10.4046/trd.2012.72.3.323. Epub 2012 Mar 31. PubMed PMID: 23227073; PubMed Central PMCID: PMC3510283. 11: Yen L, Wu J, Hodgkins PL, Cohen RD, Nichol MB. Medication use patterns and predictors of nonpersistence and nonadherence with oral 5-aminosalicylic acid therapy in patients with ulcerative colitis. J Manag Care Pharm. 2012 Nov-Dec;18(9):701-12. PubMed PMID: 23206213. 12: Love BL, Miller AD. Extended-release mesalamine granules for ulcerative colitis. Ann Pharmacother. 2012 Nov;46(11):1529-36. doi: 10.1345/aph.1R171. Epub 2012 Oct 31. Review. PubMed PMID: 23115226. 13: Feagan BG, Macdonald JK. Oral 5-aminosalicylic acid for maintenance of remission in ulcerative colitis. Cochrane Database Syst Rev. 2012 Oct 17;10:CD000544. doi: 10.1002/14651858.CD000544.pub3. Review. PubMed PMID: 23076890. 14: Unlü C, Daniels L, Vrouenraets BC, Boermeester MA. Systematic review of medical therapy to prevent recurrent diverticulitis. Int J Colorectal Dis. 2012 Sep;27(9):1131-6. doi: 10.1007/s00384-012-1486-7. Epub 2012 May 11. Review. PubMed PMID: 22576905. 15: Kane SV, Sumner M, Solomon D, Jenkins M. Twelve-month persistency with oral 5-aminosalicylic acid therapy for ulcerative colitis: results from a large pharmacy prescriptions database. Dig Dis Sci. 2011 Dec;56(12):3463-70. doi: 10.1007/s10620-011-1877-6. Epub 2011 Aug 31. PubMed PMID: 21879279. 16: Ryan A, Wang CJ, Laurieri N, Westwood I, Sim E. Reaction mechanism of azoreductases suggests convergent evolution with quinone oxidoreductases. Protein Cell. 2010 Aug;1(8):780-90. doi: 10.1007/s13238-010-0090-2. Epub 2010 Aug 28. PubMed PMID: 21203919. 17: McGrane J, Paravasthu M, Candlish W, Gravil J. Unilateral balsalazide-induced eosinophilic pneumonia in an ulcerative colitis patient. J R Coll Physicians Edinb. 2010 Sep;40(3):216-8. doi: 10.4997/JRCPE.2010.307. PubMed PMID: 21127763. 18: Ryan A, Laurieri N, Westwood I, Wang CJ, Lowe E, Sim E. A novel mechanism for azoreduction. J Mol Biol. 2010 Jul 2;400(1):24-37. doi: 10.1016/j.jmb.2010.04.023. Epub 2010 Apr 24. PubMed PMID: 20417637. 19: Wang CJ, Laurieri N, Abuhammad A, Lowe E, Westwood I, Ryan A, Sim E. Role of tyrosine 131 in the active site of paAzoR1, an azoreductase with specificity for the inflammatory bowel disease prodrug balsalazide. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2010 Jan 1;66(Pt 1):2-7. doi: 10.1107/S1744309109044741. Epub 2009 Dec 25. PubMed PMID: 20057057; PubMed Central PMCID: PMC2805523. 20: Terdiman JP, Johnson LK, Kim YS, Sleisenger MH, Gum JR, Hayes A, Weinberg VK, McQuaid KR. Chemoprevention of colonic polyps with balsalazide: an exploratory, double-blind, placebo-controlled study. Dig Dis Sci. 2009 Nov;54(11):2488-96. doi: 10.1007/s10620-009-0966-2. PubMed PMID: 19757048; PubMed Central PMCID: PMC2762046.