MSDC-0602 | CAS#1133819-87-0 | insulin sensitizer

MedKoo Cat#: 529205 | Name: MSDC-0602

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Description:

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

MSDC-0602 is an insulin sensitizer potentially for the treatment of diabetes (metabolic modulator).

Chemical Structure

MSDC-0602

CAS#1133819-87-0 (free base)

Theoretical Analysis

MedKoo Cat#: 529205

Name: MSDC-0602

CAS#: 1133819-87-0 (free base)

Chemical Formula: C19H17NO5S

Exact Mass: 371.0827

Molecular Weight: 371.41

Elemental Analysis: C, 61.44; H, 4.61; N, 3.77; O, 21.54; S, 8.63

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 250.00
100mg	USD 450.00
200mg	USD 850.00
500mg	USD 1,850.00
1g	USD 2,950.00
2g	USD 4,850.00

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Related CAS #

1133819-87-0 (free base) 1314533-26-0 (sodium) 1314533-27-1 (potassium)

Synonym

Azemiglitazone, MSDC-0602; MSDC0602; MSDC 0602

IUPAC/Chemical Name

5-(4-(2-(3-methoxyphenyl)-2-oxoethoxy)benzyl)thiazolidine-2,4-dione

InChi Key

YAUMOGALQJYOJQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H17NO5S/c1-24-15-4-2-3-13(10-15)16(21)11-25-14-7-5-12(6-8-14)9-17-18(22)20-19(23)26-17/h2-8,10,17H,9,11H2,1H3,(H,20,22,23)

SMILES Code

O=C(N1)SC(CC2=CC=C(OCC(C3=CC=CC(OC)=C3)=O)C=C2)C1=O

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

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

Certificate of Analysis

View CoA: current batch, Lot#T8R09C24

View CoA: previous batch, Lot#T8R03C19

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Azemiglitazone (MSDC-0602), a PPARγ-sparing thiazolidinedione (TZD), interacts with the mitochondrial pyruvate carrier (MPC) and inhibits its activity and has the potential for type 2 diabetes study with reducing risk of PPARγ-mediated side effects.

In vitro activity:

Isolated hepatocytes from LS-Mpc2−/− mice produced significantly less glucose compared to fl/fl hepatocytes when stimulated with pyruvate in vitro (Figure 2A). Chemical inhibition of pyruvate import by UK-5099 or MSDC-0602 also decreased glucose production in fl/fl hepatocytes, but were largely without effect on glucose production by LS-Mpc2−/− hepatocytes (Figure 2A). Reference: Cell Metab. 2015 Oct 6;22(4):682-94. https://pubmed.ncbi.nlm.nih.gov/26344101/

In vivo activity:

In a subset of mice, HTF-C (fat, fructose, and cholesterol) diet was fed for 4 weeks, and then MSDC-0602 was added to the HTF-C diet for the remaining 12 weeks (HTF-C+0602). MSDC-0602 feeding suppressed body weight gain (Figure 1A) and adiposity (Supplemental Figure 1A,B) independently of changes in food intake (Supplemental Figure 1C). The attenuation in body weight gain and adiposity was correlated with a marked increase in the mass of the intrascapular brown adipose tissue (Supplemental Figure 1D), consistent with MSDC-0602 directly stimulating differentiation of brown adipocyte progenitor cells and suggesting that increased energy expenditure explains the effects on body weight. Reference: Hepatology. 2017 May;65(5):1543-1556. https://pubmed.ncbi.nlm.nih.gov/28027586/

	Solvent	mg/mL	mM
Solubility
	DMSO	77.5	208.67
	DMSO:PBS (pH 7.2) (1:3)	0.3	0.67
	Ethanol	10.0	26.92

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 371.41 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. Zhu B, Wei X, Narasimhan H, Qian W, Zhang R, Cheon IS, Wu Y, Li C, Jones RG, Kaplan MH, Vassallo RA, Braciale TJ, Somerville L, Colca JR, Pandey A, Jackson PEH, Mann BJ, Krawczyk CM, Sturek JM, Sun J. Inhibition of the mitochondrial pyruvate carrier simultaneously mitigates hyperinflammation and hyperglycemia in COVID-19. Sci Immunol. 2023 Feb 23:eadf0348. doi: 10.1126/sciimmunol.adf0348. Epub ahead of print. PMID: 36821695; PMCID: PMC9972900. 2. McCommis KS, Hodges WT, Brunt EM, Nalbantoglu I, McDonald WG, Holley C, Fujiwara H, Schaffer JE, Colca JR, Finck BN. Targeting the mitochondrial pyruvate carrier attenuates fibrosis in a mouse model of nonalcoholic steatohepatitis. Hepatology. 2017 May;65(5):1543-1556. doi: 10.1002/hep.29025. Epub 2017 Mar 30. PMID: 28027586; PMCID: PMC5397348.

In vitro protocol:

1. McCommis KS, Chen Z, Fu X, McDonald WG, Colca JR, Kletzien RF, Burgess SC, Finck BN. Loss of Mitochondrial Pyruvate Carrier 2 in the Liver Leads to Defects in Gluconeogenesis and Compensation via Pyruvate-Alanine Cycling. Cell Metab. 2015 Oct 6;22(4):682-94. doi: 10.1016/j.cmet.2015.07.028. Epub 2015 Sep 3. PMID: 26344101; PMCID: PMC4598280.

In vivo protocol:

1: McCommis KS, Hodges WT, Brunt EM, Nalbantoglu I, McDonald WG, Holley C, Fujiwara H, Schaffer JE, Colca JR, Finck BN. Targeting the Mitochondrial Pyruvate Carrier Attenuates Fibrosis in a Mouse Model of Nonalcoholic Steatohepatitis. Hepatology. 2016 Dec 27. doi: 10.1002/hep.29025. [Epub ahead of print] PubMed PMID: 28027586. 2: Fukunaga T, Zou W, Rohatgi N, Colca JR, Teitelbaum SL. An insulin-sensitizing thiazolidinedione, which minimally activates PPARγ, does not cause bone loss. J Bone Miner Res. 2015 Mar;30(3):481-8. doi: 10.1002/jbmr.2364. PubMed PMID: 25257948; PubMed Central PMCID: PMC4472363. 3: Chen Z, Vigueira PA, Chambers KT, Hall AM, Mitra MS, Qi N, McDonald WG, Colca JR, Kletzien RF, Finck BN. Insulin resistance and metabolic derangements in obese mice are ameliorated by a novel peroxisome proliferator-activated receptor γ-sparing thiazolidinedione. J Biol Chem. 2012 Jul 6;287(28):23537-48. doi: 10.1074/jbc.M112.363960. PubMed PMID: 22621923; PubMed Central PMCID: PMC3390629. 4: Colca JR, McDonald WG, Cavey GS, Cole SL, Holewa DD, Brightwell-Conrad AS, Wolfe CL, Wheeler JS, Coulter KR, Kilkuskie PM, Gracheva E, Korshunova Y, Trusgnich M, Karr R, Wiley SE, Divakaruni AS, Murphy AN, Vigueira PA, Finck BN, Kletzien RF. Identification of a mitochondrial target of thiazolidinedione insulin sensitizers (mTOT)--relationship to newly identified mitochondrial pyruvate carrier proteins. PLoS One. 2013 May 15;8(5):e61551. doi: 10.1371/journal.pone.0061551. PubMed PMID: 23690925; PubMed Central PMCID: PMC3655167.