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MedKoo Cat#: 524366 | Name: Balaglitazone
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Description:

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

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
Balaglitazone
CAS#199113-98-9

Theoretical Analysis

MedKoo Cat#: 524366

Name: Balaglitazone

CAS#: 199113-98-9

Chemical Formula: C20H17N3O4S

Exact Mass: 395.0940

Molecular Weight: 395.43

Elemental Analysis: C, 60.75; H, 4.33; N, 10.63; O, 16.18; S, 8.11

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 750.00 2 Weeks
25mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
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
More Info
Product Data
Product Data
Instruction
View handling instruction
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
Solvent mg/mL mM
Solubility
DMF 30.0 75.87
DMSO 65.0 164.38
DMSO:PBS (pH 7.2) (1:3) 0.3 0.63
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 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.

Recalculate based on batch purity %
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
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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Wallichinine

Wallichinine