Darglitazone sodium

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

MedKoo CAT#: 413467

CAS#: 141683-98-9 (Na)

Description: Darglitazone sodium is the salt form of Darglitazone, a member of the thiazolidinedione class of drugs and an agonist of peroxisome proliferator-activated receptor-γ (PPAR-γ), an orphan member of the nuclear receptor superfamily of transcription factors. It has a variety of insulin-sensitizing effects, such as improving glycemic and lipidemic control, and is used in the treatment of metabolic disorders such as type II diabetes. Darglitazone sodium had been in phase I clinical trials by Pfizer for the treatment of type 2 diabetes. However, this study has been discontinued.

Chemical Structure

img
Darglitazone sodium
CAS# 141683-98-9 (Na)
Instruction

Theoretical Analysis

MedKoo Cat#: 413467
Name: Darglitazone sodium
CAS#: 141683-98-9 (Na)
Chemical Formula: C23H19N2NaO4S
Exact Mass: 442.10
Molecular Weight: 442.460
Elemental Analysis: C, 62.44; H, 4.33; N, 6.33; Na, 5.20; O, 14.46; S, 7.25

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Related CAS #: 141683-98-9 (Na)   141200-24-0 (free)  

Synonym: Darglitazone sodium; CP86,325-2; CP 86,325-2; CP-86,325-2

IUPAC/Chemical Name: (+-)-5-(p-(3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl)benzyl)-2,4-thiazolidinedione, sodium salt

InChi Key: AMCPCELVARAPHJ-UHFFFAOYSA-M

InChi Code: InChI=1S/C23H20N2O4S.Na/c1-14-18(24-22(29-14)17-5-3-2-4-6-17)11-12-19(26)16-9-7-15(8-10-16)13-20-21(27)25-23(28)30-20;/h2-10,20H,11-13H2,1H3,(H,25,27,28);/q;+1/p-1

SMILES Code: O=C([N-]1)SC(CC2=CC=C(C(CCC3=C(C)OC(C4=CC=CC=C4)=N3)=O)C=C2)C1=O.[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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: to be determined

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:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
To be determined 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 442.46 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:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Kumari R, Willing LB, Patel SD, Krady JK, Zavadoski WJ, Gibbs EM, Vannucci SJ, Simpson IA. The PPAR-gamma agonist, darglitazone, restores acute inflammatory responses to cerebral hypoxia-ischemia in the diabetic ob/ob mouse. J Cereb Blood Flow Metab. 2010 Feb;30(2):352-60. doi: 10.1038/jcbfm.2009.221. PubMed PMID: 19861974; PubMed Central PMCID: PMC2949120.

2: Nadanaciva S, Dykens JA, Bernal A, Capaldi RA, Will Y. Mitochondrial impairment by PPAR agonists and statins identified via immunocaptured OXPHOS complex activities and respiration. Toxicol Appl Pharmacol. 2007 Sep 15;223(3):277-87. PubMed PMID: 17658574.

3: Li M, Pan LC, Simmons HA, Li Y, Healy DR, Robinson BS, Ke HZ, Brown TA. Surface-specific effects of a PPARgamma agonist, darglitazone, on bone in mice. Bone. 2006 Oct;39(4):796-806. PubMed PMID: 16759917.

4: Aleo MD, Doshna CM, Navetta KA. Ciglitazone-induced lenticular opacities in rats: in vivo and whole lens explant culture evaluation. J Pharmacol Exp Ther. 2005 Mar;312(3):1027-33. PubMed PMID: 15523002.

5: Floyd ZE, Stephens JM. Control of peroxisome proliferator-activated receptor gamma2 stability and activity by SUMOylation. Obes Res. 2004 Jun;12(6):921-8. PubMed PMID: 15229330.

6: Zawalich WS, Tesz G, Zawalich KC. Contrasting effects of nateglinide and rosiglitazone on insulin secretion and phospholipase C activation. Metabolism. 2003 Nov;52(11):1393-9. PubMed PMID: 14624396.

7: Hoenig M, Ferguson DC. Effect of darglitazone on glucose clearance and lipid metabolism in obese cats. Am J Vet Res. 2003 Nov;64(11):1409-13. PubMed PMID: 14620778.

8: Salomonsson L, Svensson L, Pettersson S, Wiklund O, Ohlsson BG. Oxidised LDL decreases VEGFR-1 expression in human monocyte-derived macrophages. Atherosclerosis. 2003 Aug;169(2):259-67. PubMed PMID: 12921977.

9: Svensson L, Camejo G, Cabré A, Vallvé JC, Pedreño J, Norén K, Wiklund O, Hultén LM. Fatty acids modulate the effect of darglitazone on macrophage CD36 expression. Eur J Clin Invest. 2003 Jun;33(6):464-71. PubMed PMID: 12795642.

10: Granlund L, Juvet LK, Pedersen JI, Nebb HI. Trans10, cis12-conjugated linoleic acid prevents triacylglycerol accumulation in adipocytes by acting as a PPARgamma modulator. J Lipid Res. 2003 Aug;44(8):1441-52. PubMed PMID: 12754280.

11: Aleo MD, Lundeen GR, Blackwell DK, Smith WM, Coleman GL, Stadnicki SW, Kluwe WM. Mechanism and implications of brown adipose tissue proliferation in rats and monkeys treated with the thiazolidinedione darglitazone, a potent peroxisome proliferator-activated receptor-gamma agonist. J Pharmacol Exp Ther. 2003 Jun;305(3):1173-82. PubMed PMID: 12626651.

12: López-Solache I, Marie V, Camirand A, Silva JE. Regulation of uncoupling protein-2 mRNA in L6 myotubules: II: Thyroid hormone amplifies stimulation of uncoupling protein-2 gene by thiazolidinediones and other peroxisome proliferator-activated receptor ligands in L6 myotubules: evidence for a priming effect. Endocrine. 2002 Nov;19(2):209-17. PubMed PMID: 12588052.

13: López-Solache I, Marie V, Vignault E, Camirand A, Silva JE. Regulation of uncoupling protein-2 mRNA in L6 myotubules: I: Thiazolidinediones stimulate uncoupling protein-2 gene expression by a mechanism requiring ongoing protein synthesis and an active mitogen-activated protein kinase. Endocrine. 2002 Nov;19(2):197-208. PubMed PMID: 12588051.

14: Juvet LK, Andresen SM, Schuster GU, Dalen KT, Tobin KA, Hollung K, Haugen F, Jacinto S, Ulven SM, Bamberg K, Gustafsson JA, Nebb HI. On the role of liver X receptors in lipid accumulation in adipocytes. Mol Endocrinol. 2003 Feb;17(2):172-82. PubMed PMID: 12554745.

15: Haugen F, Jørgensen A, Drevon CA, Trayhurn P. Inhibition by insulin of resistin gene expression in 3T3-L1 adipocytes. FEBS Lett. 2001 Oct 19;507(1):105-8. PubMed PMID: 11682067.

16: Oakes ND, Thalén PG, Jacinto SM, Ljung B. Thiazolidinediones increase plasma-adipose tissue FFA exchange capacity and enhance insulin-mediated control of systemic FFA availability. Diabetes. 2001 May;50(5):1158-65. PubMed PMID: 11334421.

17: Bakopanos E, Silva JE. Thiazolidinediones inhibit the expression of beta3-adrenergic receptors at a transcriptional level. Diabetes. 2000 Dec;49(12):2108-15. PubMed PMID: 11118014.

18: Aleo MD, Avery MJ, Beierschmitt WP, Drupa CA, Fortner JH, Kaplan AH, Navetta KA, Shepard RM, Walsh CM. The use of explant lens culture to assess cataractogenic potential. Ann N Y Acad Sci. 2000;919:171-87. PubMed PMID: 11083107.

19: Olsson U, Bondjers G, Camejo G. Fatty acids modulate the composition of extracellular matrix in cultured human arterial smooth muscle cells by altering the expression of genes for proteoglycan core proteins. Diabetes. 1999 Mar;48(3):616-22. PubMed PMID: 10078565.

20: Camirand A, Marie V, Rabelo R, Silva JE. Thiazolidinediones stimulate uncoupling protein-2 expression in cell lines representing white and brown adipose tissues and skeletal muscle. Endocrinology. 1998 Jan;139(1):428-31. PubMed PMID: 9421444.