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Imeglimin HCl

Alias: Imeglimin HCl EMD387008 hydrochlorideImeglimin hydrochloride EMD387008 HCl
Cat No.:V5818 Purity: ≥98%
Imeglimin HCl (EMD 387008 HCl) is an oral hypoglycemic agent.
Imeglimin HCl
Imeglimin HCl Chemical Structure CAS No.: 775351-61-6
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
50mg
100mg
250mg
Other Sizes

Other Forms of Imeglimin HCl:

  • Imeglimin
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Imeglimin HCl (EMD 387008 HCl) is an oral hypoglycemic agent. Imeglimin improves insulin sensitivity. Imeglimin also reduces the production of reactive oxygen species (ROS), increases mitochondrial DNA, and improves mitochondrial function.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Complete prevention of cell death induced by tert-butyl hydroperoxide (tBH) was similarly achieved by preincubation with Imeglimin (10 mM, 4 h or 100 μM, 24 h) [2].
ln Vivo
During the final six weeks of HFHSD feeding, meglimin (200 mg/kg b.i.d. orally) dramatically lowers hyperglycemia and returns normal glucose tolerance [1].
Cell Assay
Cell Viability Assay [2]
Cell Types: Human Endothelial Cells (HMEC-1)
Tested Concentrations: 100 μM and 10 mM
Incubation Duration: 100 μM 24 hrs (hours), 10 mM 4 hrs (hours)
Experimental Results: Prevents cell death.
Animal Protocol
Animal/Disease Models: Male C57BL/6JOlaHsd mice (4 weeks old) [1]
Doses: 200 mg/kg
Route of Administration: po (oral gavage); bid; 6 weeks
Experimental Results: A slight decrease in body weight and food intake was observed, and There is some diarrhea, but only during the first few days of treatment.
References

[1]. Imeglimin normalizes glucose tolerance and insulin sensitivity and improves mitochondrialfunction in liver of a high-fat, high-sucrose diet mice model. Diabetes. 2015 Jun;64(6):2254-64.

[2]. Imeglimin prevents human endothelial cell death by inhibiting mitochondrial permeability transition without inhibiting mitochondrial respiration. Cell Death Discov. 2016 Jan 18;2:15072.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H14CLN5
Molecular Weight
191.6619
Exact Mass
191.093
CAS #
775351-61-6
Related CAS #
Imeglimin;775351-65-0
PubChem CID
54763513
Appearance
White to off-white solid powder
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Heavy Atom Count
12
Complexity
205
Defined Atom Stereocenter Count
1
SMILES
Cl[H].N(C([H])([H])[H])(C([H])([H])[H])C1=N[C@]([H])(C([H])([H])[H])N=C(N([H])[H])N1[H]
InChi Key
UXHLCYMTNMEXKZ-PGMHMLKASA-N
InChi Code
InChI=1S/C6H13N5.ClH/c1-4-8-5(7)10-6(9-4)11(2)3;/h4H,1-3H3,(H3,7,8,9,10);1H/t4-;/m1./s1
Chemical Name
(4R)-6-N,6-N,4-trimethyl-1,4-dihydro-1,3,5-triazine-2,6-diamine;hydrochloride
Synonyms
Imeglimin HCl EMD387008 hydrochlorideImeglimin hydrochloride EMD387008 HCl
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

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
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)
H2O : ≥ 50 mg/mL (~260.88 mM)
DMSO : ~25 mg/mL (~130.44 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (10.85 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 (10.85 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.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (10.85 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.


Solubility in Formulation 4: 100 mg/mL (521.76 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.2176 mL 26.0879 mL 52.1757 mL
5 mM 1.0435 mL 5.2176 mL 10.4351 mL
10 mM 0.5218 mL 2.6088 mL 5.2176 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

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

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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?
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  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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.)
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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.

(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.

Biological Data
  • Effect of Imeglimin on tBH- or hyperglycemia-induced endothelial cell death. HMEC-1 cells incubated in the absence or presence of either 100 μM Imeglimin for 24 h, 10 mM Imeglimin for 4 h or 1 μM CsA for 30 min were washed with PBS before subsequent exposure to 0.5 mM tBH or vehicle (control) in FBS-free culture medium for 45 min. Cells were then washed with PBS and incubated at 37 °C for 24 h in a complete MCDB medium. Alternatively, HMEC-1 cells were cultured for 48 h in a complete MCDB medium at the indicated concentration of glucose, in the absence or presence of 1 μM CsA, 250 μM N-acetyl cysteine (NAC) or 100 μM imeglimin. Cytotoxicity was evaluated by staining cells with Alexa Fluor-conjugated annexin V and PI. (a and b) Representative data. (c and d) Percentage of dead cells (i.e., cells positive for annexin V or PI) in five different experiments. Results are mean±S.E.M.; # P<0.01, *P<0.05 versus control cells, paired Student’s t-test.[2]. Detaille D, et al. Imeglimin prevents human endothelial cell death by inhibiting mitochondrial permeability transition without inhibiting mitochondrial respiration. Cell Death Discov. 2016 Jan 18;2:15072.
  • Effect of Imeglimin on cytochrome c distribution. HMEC-1 cells incubated in the presence or absence of Imeglimin were exposed to tBH or to hyperglycemic conditions as described in Figure 1. After 24 or 48 h (for tBH treatment and hyperglycemia, respectively), immunostaining was performed with specific anti-cytochrome c antibody. Representative data of five different experiments. Scale bar: 40 μm.[2]. Detaille D, et al. Imeglimin prevents human endothelial cell death by inhibiting mitochondrial permeability transition without inhibiting mitochondrial respiration. Cell Death Discov. 2016 Jan 18;2:15072.
  • Effects of Imeglimin on the Ca2+ retention capacity of digitonin-permeabilized HMEC-1 cells. (a) The incubation medium contained 250 mM sucrose, 1 mM Pi, 10 mM Tris-MOPS, 0.25 μM Calcium Green-5N, 50 μg/ml digitonin and either 5 mM succinate or 5 mM glutamate plus 2.5 mM malate. The final volume was 1 ml (pH 7.35) at 25 °C. Experiments were started by the addition of 107 HMEC-1 cells. Where indicated, 12.5 μM Ca2+ pulses were added (arrows). Panel (b) represents cumulative data of five different experiments performed as described in the panel (a) after preincubation with CsA (1 μM for 30 min) or Imeglimin (100 μM for 24 h). Results are mean±S.E.M.; # P<0.01; *P<0.05 versus control cells, paired Student’s t-test.[2]. Detaille D, et al. Imeglimin prevents human endothelial cell death by inhibiting mitochondrial permeability transition without inhibiting mitochondrial respiration. Cell Death Discov. 2016 Jan 18;2:15072.
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