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Purity: ≥98%
Ezatiostat (formerly known as TER199; TLK199; Brand name: Telentra) is a glutathione analog inhibitor of glutathione S-transferase P1-1 (GSTP1-1). It was shown that an ezatiostat response profile contains two miRNAs that regulate expression of genes known to be implicated in MDS disease pathology. Remarkably, pathway analysis of the response profile revealed that the genes comprising the jun-N-terminal kinase/c-Jun molecular pathway, which is known to be activated by ezatiostat, are under-expressed in patients who respond and over-expressed in patients who were non-responders to the drug, suggesting that both the biology of the disease and the molecular mechanism of action of the drug are positively correlated.
| ln Vitro |
When ezatiostat dissociates the enzyme from the jun-N-terminal kinase/c-Jun (JNK/JUN) complex, phosphorylation of JNK results in JNK activation. Ezatiostat appears to have both malignant clone apoptosis and normal myeloid progenitor cell growth as therapeutic effects [1]. Selecting resistant clones of the HL60 tumor cell line through prolonged exposure to ezatiostat (TLK199) causes high levels of apoptosis in cells and increases the activity of c-Jun NH2-terminal kinase (JNK1) and ERK1/ERK2 in cells, allowing them to proliferate under stress conditions in comparison to wild type [2].
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| ln Vivo |
Ezatiostat (TLK199) administration increases the generation of lymphocytes and the proliferation of myeloid progenitor cells (colony forming units, granulocyte macrophages), but only in mice that are glutathione S-transferase P1-1 (GSTP1+/+) and not in GSTP1-/- animals. 2].
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| References | |
| Additional Infomation |
Ezatiostat is investigated in clinical trials for treating myelodysplastic syndrome. This compound belongs to the peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. This medication is known to target Glutathione S-transferase P. Ezatiostat is a small molecule drug that is an analog inhibitor of glutathione S-transferase P1-1. It acts intracellularly on the MAPK signaling pathway by activating ERK2. Ezatiostat has myelostimulant activity in preclinical rodent models and human bone marrow cultures, and differentiates granulocytes and monocytes in HL60 cells. Ezatiostat is a candidate designed to stimulate the formation of bone marrow cells that are precursors to granulocytes and monocytes (white blood cells), erythrocytes (red blood cells) and platelets. Many conditions are characterized by depleted bone marrow, including myelodysplastic syndrome (MDS), a form of pre-leukemia in which the bone marrow produces insufficient levels of one or more of the 3 major blood elements (white blood cells, red blood cells and platelets). It might also be relevant as an adjunct therapy since a reduction in blood cell levels is also a common, toxic effect of many standard chemotherapeutic drugs.
Drug Indication Investigated for use/treatment in myelodysplastic syndrome. |
| Molecular Formula |
C27H35N3O6S
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|---|---|
| Molecular Weight |
529.6483
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| Exact Mass |
529.224
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| CAS # |
168682-53-9
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| Related CAS # |
TLK117;152684-53-2;Ezatiostat hydrochloride;286942-97-0
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| PubChem CID |
5310939
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
749.7±60.0 °C at 760 mmHg
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| Flash Point |
407.2±32.9 °C
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| Vapour Pressure |
0.0±2.5 mmHg at 25°C
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| Index of Refraction |
1.569
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| LogP |
4.27
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
17
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| Heavy Atom Count |
37
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| Complexity |
725
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| Defined Atom Stereocenter Count |
3
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| SMILES |
CCOC(=O)[C@H](CCC(=O)N[C@@H](CSCC1=CC=CC=C1)C(=O)N[C@H](C2=CC=CC=C2)C(=O)OCC)N
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| InChi Key |
GWEJFLVSOGNLSS-FIXSFTCYSA-N
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| InChi Code |
InChI=1S/C27H35N3O6S/c1-3-35-26(33)21(28)15-16-23(31)29-22(18-37-17-19-11-7-5-8-12-19)25(32)30-24(27(34)36-4-2)20-13-9-6-10-14-20/h5-14,21-22,24H,3-4,15-18,28H2,1-2H3,(H,29,31)(H,30,32)/t21-,22-,24-/m0/s1
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| Chemical Name |
(S)-ethyl 2-amino-5-(((R)-3-(benzylthio)-1-(((S)-2-ethoxy-2-oxo-1-phenylethyl)amino)-1-oxopropan-2-yl)amino)-5-oxopentanoate
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| Synonyms |
TLK199; TLK-199; TLK 199; Ezatiostat; TER-199; TLK-199 hydrochloride; TER 199; TLK 199 hydrochloride; TER199; TLK199 hydrochloride; trade name: Telintra
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
Ethanol :≥ 100 mg/mL (~188.80 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.75 mg/mL (5.19 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 27.5 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: 2.75 mg/mL (5.19 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 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: ≥ 2.75 mg/mL (5.19 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.8880 mL | 9.4402 mL | 18.8804 mL | |
| 5 mM | 0.3776 mL | 1.8880 mL | 3.7761 mL | |
| 10 mM | 0.1888 mL | 0.9440 mL | 1.8880 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.
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.
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