Balaglitazone | CAS#199113-98-9 | PPARγ Agonist

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

MedKoo CAT#: 524366

CAS#: 199113-98-9

Description: Balaglitazone is an agonist of peroxisome proliferator-activated receptor (PPAR) γ. Balaglitazone plays an important role in the regulation of insulin, triglycerides and lipid metabolism. It is an attractive target for the therapy of Type II Diabetes.

Chemical Structure

Balaglitazone

CAS# 199113-98-9

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 524366
Name: Balaglitazone
CAS#: 199113-98-9
Chemical Formula: C20H17N3O4S
Exact Mass: 395.09
Molecular Weight: 395.430
Elemental Analysis: C, 60.75; H, 4.33; N, 10.63; O, 16.18; S, 8.11

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 280
5mg	USD 665
10mg	USD 1095
25mg	USD 2050
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Balaglitazone; DRF-2593; NNC-61-0645; NNC-61-2344; NN-2344; NNC-610645; NNC-612344.

IUPAC/Chemical Name: 5-(p-((3,4-Dihydro-3-methyl-4-oxo-2-quinazolinyl)methoxy)benzyl)-2,4-thiazolidinedione

InChi Key: IETKPTYAGKZLKY-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H17N3O4S/c1-23-17(21-15-5-3-2-4-14(15)19(23)25)11-27-13-8-6-12(7-9-13)10-16-18(24)22-20(26)28-16/h2-9,16H,10-11H2,1H3,(H,22,24,26)

SMILES Code: Cn1c(nc2ccccc2c1=O)COc3ccc(cc3)CC4C(=O)NC(=O)S4

Appearance: A crystalline solid

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

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Product Data:

Product Data

Instruction:

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Biological target:	Balaglitazone is a PPARγ agonist with an EC50 of 1.351 μM for human PPARγ.
In vitro activity:	Balaglitazone considerably enhanced the cytotoxicity of doxorubicin in human myelogenous leukemia (K562/DOX) cells. Balaglitazone also significantly downregulated P-glycoprotein expression and activity in K562/DOX cells and reduced multidrug resistance through elevation of intracellular doxorubicin in cells. Furthermore, upon balaglitazone treatment, phosphatase and tensin homolog deleted on chromosome 10 expression could be restored in K562/DOX cells in a peroxisome proliferator-activated receptor γ-dependent manner. These results suggested that balaglitazone could reverse multidrug resistance by inducing phosphatase and tensin homolog deleted on chromosome 10 and peroxisome proliferator-activated receptor/ phosphatase and tensin homolog deleted on chromosome 10 signaling pathway. Reference: Tumour Biol. 2017 Oct;39(10):1010428317716501. https://journals.sagepub.com/doi/10.1177/1010428317716501?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%20%200pubmed
In vivo activity:	TBD

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	75.87
	DMSO	65.0	164.38
	DMSO:PBS (pH 7.2) (1:3)	0.3	0.63

Preparing Stock Solutions

The following data is based on the product molecular weight 395.43 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. Yousefi B, Azimi A, Majidinia M, Shafiei-Irannejad V, Badalzadeh R, Baradaran B, Zarghami N, Samadi N. Balaglitazone reverses P-glycoprotein-mediated multidrug resistance via upregulation of PTEN in a PPARγ-dependent manner in leukemia cells. Tumour Biol. 2017 Oct;39(10):1010428317716501. doi: 10.1177/1010428317716501. PMID: 28978268.
In vitro protocol:	1. Yousefi B, Azimi A, Majidinia M, Shafiei-Irannejad V, Badalzadeh R, Baradaran B, Zarghami N, Samadi N. Balaglitazone reverses P-glycoprotein-mediated multidrug resistance via upregulation of PTEN in a PPARγ-dependent manner in leukemia cells. Tumour Biol. 2017 Oct;39(10):1010428317716501. doi: 10.1177/1010428317716501. PMID: 28978268.
In vivo protocol:	TBD

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1: Agrawal R, Jain P, Dikshit SN. Balaglitazone: a second generation peroxisome proliferator-activated receptor (PPAR) gamma (γ) agonist. Mini Rev Med Chem. 2012 Feb;12(2):87-97. doi: 10.2174/138955712798995048. PMID: 22372600.

2: Yousefi B, Azimi A, Majidinia M, Shafiei-Irannejad V, Badalzadeh R, Baradaran B, Zarghami N, Samadi N. Balaglitazone reverses P-glycoprotein-mediated multidrug resistance via upregulation of PTEN in a PPARγ-dependent manner in leukemia cells. Tumour Biol. 2017 Oct;39(10):1010428317716501. doi: 10.1177/1010428317716501. PMID: 28978268.

3: Henriksen K, Byrjalsen I, Qvist P, Beck-Nielsen H, Hansen G, Riis BJ, Perrild H, Svendsen OL, Gram J, Karsdal MA, Christiansen C; BALLET Trial Investigators. Efficacy and safety of the PPARγ partial agonist balaglitazone compared with pioglitazone and placebo: a phase III, randomized, parallel-group study in patients with type 2 diabetes on stable insulin therapy. Diabetes Metab Res Rev. 2011 May;27(4):392-401. doi: 10.1002/dmrr.1187. PMID: 21328517.

4: Larsen PJ, Lykkegaard K, Larsen LK, Fleckner J, Sauerberg P, Wassermann K, Wulff EM. Dissociation of antihyperglycaemic and adverse effects of partial perioxisome proliferator-activated receptor (PPAR-gamma) agonist balaglitazone. Eur J Pharmacol. 2008 Oct 31;596(1-3):173-9. doi: 10.1016/j.ejphar.2008.08.004. Epub 2008 Aug 16. PMID: 18761337.

5: Henriksen K, Byrjalsen I, Nielsen RH, Madsen AN, Larsen LK, Christiansen C, Beck-Nielsen H, Karsdal MA. A comparison of glycemic control, water retention, and musculoskeletal effects of balaglitazone and pioglitazone in diet-induced obese rats. Eur J Pharmacol. 2009 Aug 15;616(1-3):340-5. doi: 10.1016/j.ejphar.2009.06.051. Epub 2009 Jul 10. PMID: 19595686.

6: Xie D, He Z, Dong Y, Gong Z, Nie G, Li Y. Molecular Cloning, Characterization, and Expression Regulation of Acyl-CoA Synthetase 6 Gene and Promoter in Common Carp Cyprinus carpio. Int J Mol Sci. 2020 Jul 3;21(13):4736. doi: 10.3390/ijms21134736. PMID: 32635148; PMCID: PMC7370118.

7: Karsdal MA, Henriksen K, Nielsen MJ, Byrjalsen I, Leeming DJ, Gardner S, Goodman Z, Patel K, Krag A, Christiansen C, Schuppan D. Fibrogenesis assessed by serological type III collagen formation identifies patients with progressive liver fibrosis and responders to a potential antifibrotic therapy. Am J Physiol Gastrointest Liver Physiol. 2016 Dec 1;311(6):G1009-G1017. doi: 10.1152/ajpgi.00283.2016. Epub 2016 Oct 20. PMID: 27765759.

8: Balakumar P, Kathuria S. Submaximal PPARγ activation and endothelial dysfunction: new perspectives for the management of cardiovascular disorders. Br J Pharmacol. 2012 Aug;166(7):1981-92. doi: 10.1111/j.1476-5381.2012.01938.x. PMID: 22404217; PMCID: PMC3402765.

9: Karsdal MA, Henriksen K, Genovese F, Leeming DJ, Nielsen MJ, Riis BJ, Christiansen C, Byrjalsen I, Schuppan D. Serum endotrophin identifies optimal responders to PPARγ agonists in type 2 diabetes. Diabetologia. 2017 Jan;60(1):50-59. doi: 10.1007/s00125-016-4094-1. Epub 2016 Sep 8. PMID: 27631136.

10: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Sep;25(7):565-97. PMID: 14571286.

11: Jamali B, Bjørnsdottir I, Cornett C, Honoré Hansen S. Investigation of a dual CD chiral CE system for separation of glitazone compounds. Electrophoresis. 2009 Aug;30(16):2853-61. doi: 10.1002/elps.200800812. PMID: 19650045.

12: Jamali B, Theill GC, Sørensen LL. Generic, highly selective and robust capillary electrophoresis method for separation of a racemic mixture of glitazone compounds. J Chromatogr A. 2004 Sep 17;1049(1-2):183-7. doi: 10.1016/j.chroma.2004.08.011. PMID: 15499931.

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