WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H317308
CAS#: 150399-21-6 ( Disodium )
Description: 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.
Hodoodo Cat#: H317308
Name: Balsalazide Disodium
CAS#: 150399-21-6 ( Disodium )
Chemical Formula: C17H17N3Na2O8
Exact Mass: 0.00
Molecular Weight: 437.310
Elemental Analysis: C, 46.69; H, 3.92; N, 9.61; Na, 10.51; O, 29.27
Related CAS #: 150399-21-6 (Disodium) 82101-18-6 (salt) 80573-04-2 (free base)
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:
| 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 | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 87.0 | 198.94 | |
| Water | 87.0 | 198.94 |
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: | 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 vivo 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. |
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.
