MSDC-0602

Alias: MSDC-0602 MSDC0602 Azemiglitazone MSDC 0602

Cat No.:V9679 Purity: ≥98%

COA Product Data Instructions for use SDS

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

MSDC-0602 Chemical Structure CAS No.: 1133819-87-0
Product category: Mitochondrial Metabolism

This product is for research use only, not for human use. We do not sell to patients.

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1-708-310-1919 sales@invivochem.com

Other Forms of MSDC-0602:

MSDC-0602K (Azemiglitazone potassium)

Official Supplier of:

Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

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Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Azemiglitazone (MSDC0602; MSDC-0602) is an insulin sensitizer potentially for the treatment of diabetes (metabolic modulator). It is a PPARγ-sparing thiazolidinedione (Ps-TZD) that binds to PPARγ with the IC50 of 18.25 μM

Biological Activity I Assay Protocols (From Reference)

References	[1]. 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. [2]. The beneficial metabolic effects of sensitizers are not attenuated by mitochondrial pyruvate carrier 2 hypomorphism. Exp Physiol. 2017 Aug 1;102(8):985-999. [3]. 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. [4]. Targeting the mitochondrial pyruvate carrier attenuates fibrosis in a mouse model of nonalcoholic steatohepatitis. Hepatology. 2017 May;65(5):1543-1556. [5]. MSDC-0160 and MSDC-0602 binding with human mitochondrial pyruvate carrier (MPC) 1 and 2 heterodimer: PPARγ activating and sparing TZDs as therapeutics. Int. J. Knowl. Knowl. Bioinform.2017, 7, 43–67. [6]. 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.
Additional Infomation	Azemiglitazone is under investigation in clinical trial NCT01280695 (A Randomized, Double-blind, Comparator- and Placebo-controlled, Multiple-dose Study to Evaluate the Safety, Tolerability and Efficacy of Three Dose Levels of MSDC-0602 in Type 2 Diabetic Patients).

References

[1]. 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.

[2]. The beneficial metabolic effects of sensitizers are not attenuated by mitochondrial pyruvate carrier 2 hypomorphism. Exp Physiol. 2017 Aug 1;102(8):985-999.

[3]. 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.

[4]. Targeting the mitochondrial pyruvate carrier attenuates fibrosis in a mouse model of nonalcoholic steatohepatitis. Hepatology. 2017 May;65(5):1543-1556.

[5]. MSDC-0160 and MSDC-0602 binding with human mitochondrial pyruvate carrier (MPC) 1 and 2 heterodimer: PPARγ activating and sparing TZDs as therapeutics. Int. J. Knowl. Knowl. Bioinform.2017, 7, 43–67.

[6]. 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.

Additional Infomation

Azemiglitazone is under investigation in clinical trial NCT01280695 (A Randomized, Double-blind, Comparator- and Placebo-controlled, Multiple-dose Study to Evaluate the Safety, Tolerability and Efficacy of Three Dose Levels of MSDC-0602 in Type 2 Diabetic Patients).

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C19H17NO5S
Molecular Weight	371.4
Exact Mass	371.082
CAS #	1133819-87-0
Related CAS #	Azemiglitazone potassium;1314533-27-1
PubChem CID	25230266
Appearance	White to off-white solid powder
Density	1.3±0.1 g/cm3
Boiling Point	608.1±40.0 °C at 760 mmHg
Flash Point	321.6±27.3 °C
Vapour Pressure	0.0±1.7 mmHg at 25°C
Index of Refraction	1.617
LogP	2.82
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Heavy Atom Count	26
Complexity	532
Defined Atom Stereocenter Count	0
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)
Chemical Name	5-(4-(2-(3-methoxyphenyl)-2-oxoethoxy)benzyl)thiazolidine-2,4-dione
Synonyms	MSDC-0602 MSDC0602 Azemiglitazone MSDC 0602
HS Tariff Code	2934.99.9001
Storage	Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)	DMSO : ~125 mg/mL (~336.56 mM) H2O : < 0.1 mg/mL
Solubility (In Vivo)	Solubility in Formulation 1: ≥ 2.08 mg/mL (5.60 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.60 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More Solubility in Formulation 3: ≥ 2.08 mg/mL (5.60 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.)

Solubility (In Vitro)

DMSO : ~125 mg/mL (~336.56 mM)
H2O : < 0.1 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (5.60 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (5.60 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

View More

Solubility in Formulation 3: ≥ 2.08 mg/mL (5.60 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.6925 mL	13.4626 mL	26.9251 mL
	5 mM	0.5385 mL	2.6925 mL	5.3850 mL
	10 mM	0.2693 mL	1.3463 mL	2.6925 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

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Concentration (End)

Volume (End)

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

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Desired Reconstitution Concentration

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT01280695	COMPLETEDWITH RESULTS	Drug: Placebo Drug: MSDC-0602 100 mg Drug: MSDC-0602 250 mg	Diabetes Mellitus, Type 2	Metabolic Solutions Development Company	2011-02	Phase 2

Biological Data

MSDC-0602 causes weight loss and in WT and MPC2 hypomorphic mice [A,B] Body weight of WT and Mpc2Δ16 mice on diets that were low fat (LF), high fat (HF), HF containing pioglitazone (HF + PIO), or HF containing MSDC-0602 (HF + 0602). [C] Average activity (Area Under the Curve) of WT mice in each diet group: high fat diet (HF), HF diet supplemented with MSDC-602 (0602), HF diet supplemented with pioglitazone (PIO) determined using an infrared-sensing device (Inframot) during the dark phase of the diurnal cycle (1800-0600), light phase (0600-1800), and the sum of both. Values are presented as the mean ± SD. HF n=11; 0602 n=12; PIO n=12; * indicates p<0.05 vs LF-fed group. † indicates p<0.05 vs HF-fed group. [D] Consumption of food by WT and Mpc2Δ16 mice on diets that were low fat (LF), high fat (HF), HF containing pioglitazone (HF + PIO), or HF containing MSDC-0602 (HF + 0602) for the first 2 weeks of TZD administration. [E] Body fat percentage determined by DEXA analysis after 3 weeks of TZD treatment. WT LF n=15; Mpc2Δ16 LF n=9; WT HF n=14; Mpc2Δ16 HF n=9; WT HF + PIO n=13; Mpc2Δ16 HF + PIO n=8; WT HF + 0602 n=13; Mpc2Δ16 HF + 0602 n=9;The beneficial metabolic effects of sensitizers are not attenuated by mitochondrial pyruvate carrier 2 hypomorphism. Exp Physiol. 2017 Aug 1;102(8):985-999.

MSDC-0602 improves glucose tolerance and hepatic steatosis [A] Results of glucose tolerance testing in WT and Mpc2Δ16 mice on LF, HF, HF containing PIO, or HF containing MSDC-0602 diets. [B] Blood glucose area under the curve (AUC) values during glucose tolerance testing for WT and Mpc2Δ16 mice on diets that were low fat (LF) or high fat (HF) after treatment with PIO, 0602, or no drug calculated using the trapezoidal rule. WT LF n=15; Mpc2Δ16 LF n=9; WT HF n=14; Mpc2Δ16 HF n=9; WT HF + PIO n=13; Mpc2Δ16 HF + PIO n=8; WT HF + 0602 n=13; Mpc2Δ16 HF + 0602 n=9; [C] Liver triacylglycerol (TAG) content in WT and Mpc2Δ16 mice on LF, HF, HF containing pioglitazone (PIO), or HF containing MSDC-0602 diets. Values are presented as the mean ± SD. WT LF n=8; Mpc2Δ16 LF n=6; WT HF n=6; Mpc2Δ16 HF n=6; WT HF + PIO n=5; Mpc2Δ16 HF + PIO n=5; WT HF + 0602 n=7; Mpc2Δ16 HF + 0602 n=5; * indicates p<0.05 vs LF-fed group. † indicates p<0.05 vs HF-fed group.The beneficial metabolic effects of sensitizers are not attenuated by mitochondrial pyruvate carrier 2 hypomorphism. Exp Physiol. 2017 Aug 1;102(8):985-999.

Diminished expression of markers of macrophage infiltration after treatment with PIO or MSDC-0602 The expression of indicated genes encoding proinflammatory cytokines, macrophage markers, and adiponectin (Adipoq) in epididymal adipose tissue of mice fed LF, HF, or HF containing PIO or MSDC-0602 diets is shown. Values are presented as the mean ± SD. N=6 per group, * indicates p<0.05 vs LF-fed group. † indicates p<0.05 vs HF-fed group.The beneficial metabolic effects of sensitizers are not attenuated by mitochondrial pyruvate carrier 2 hypomorphism. Exp Physiol. 2017 Aug 1;102(8):985-999.