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Ezatiostat

CAT: 0804-HY-13634A-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-13634A-01Size:5 mg
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Description
Ezatiostat (TER199 free base; TLK199) is a tripeptide analog of glutathione and is a selective and orally active glutathione S-transferase P1-1 (GSTP1) inhibitor. Ezatiostat leads to JNK activation by inhibiting GSTP1. Ezatiostat stimulates both lymphocyte production and bone marrow progenitor proliferation. Ezatiostat has the potential for myelodysplastic syndrome (MDS) treatment[1][2].
CAS Number
168682-53-9
Product Name Alternative
TER199 (free base) ; TLK199
UNSPSC
12352209
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Glutathione S-transferase
Type
Peptides
Related Pathways
Apoptosis; Metabolic Enzyme/Protease
Applications
Cancer-Kinase/protease
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/ezatiostat.html
Purity
99.82
Solubility
DMSO : 100 mg/mL (ultrasonic) |Ethanol : ≥ 100 mg/mL
Smiles
O=C(OCC)[C@@H](C1=CC=CC=C1)NC([C@@H](NC(CC[C@H](N)C(OCC)=O)=O)CSCC2=CC=CC=C2)=O
Molecular Formula
C27H35N3O6S
Molecular Weight
529.65
Precautions
H302, H315, H319, H335
References & Citations
[1]Galili N, et al. Prediction of response to therapy with ezatiostat in lower risk myelodysplastic syndrome. J Hematol Oncol. 2012 May 6;5:20|[2]Ruscoe JE, et al. Pharmacologic or genetic manipulation of glutathione S-transferase P1-1 (GSTpi) influences cell proliferation pathways. J Pharmacol Exp Ther. 2001 Jul;298 (1) :339-45.
Shipping Conditions
Blue Ice
Storage Conditions
-80°C, 2 years; -20°C, 1 year (Powder, sealed storage, away from moisture)
Scientific Category
Peptides
Clinical Information
Phase 2
Citation 01
Adv Sci (Weinh) . 2023 Mar;10 (7) :e2205262.|Arch Biochem Biophys. 2024 Jul:757:110043.|Cell Res. 2018 Dec;28 (12) :1171-1185. |Free Radic Biol Med. 2024 Jun 19:S0891-5849 (24) 00531-8.|Phytomedicine. 2024 Aug 31:134:155989.|Redox Biol. 2023 May:61:102635.|Redox Biol. 2024 Aug 20:76:103323.|Cancer Biomark. 2025 Oct;42 (10) :18758592251390145.

Chemical Information

Ezatiostat

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.

CAS Number168682-53-9
PubChem CID5310939
IUPAC Nameethyl (2S)-2-amino-5-[[(2R)-3-benzylsulfanyl-1-[[(1R)-2-ethoxy-2-oxo-1-phenylethyl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoate
Molecular FormulaC27H35N3O6S
Molecular Weight529.6
XLogP2.7
Topological Polar Surface Area162
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count17
Heavy Atom Count37
Formal Charge0
Complexity725
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
InChI
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
InChIKey
GWEJFLVSOGNLSS-WPFOTENUSA-N
Chemical Structure
2D Structure
2D structure of Ezatiostat
CAS: 168682-53-9
CID: 5310939
Formula: C27H35N3O6S
MW: 529.6
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight529.6
XLogP32.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count17
Exact Mass529.22465702
Monoisotopic Mass529.22465702
Topological Polar Surface Area162 Ų
Heavy Atom Count37
Formal Charge0
Complexity725
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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