SML1081

Ezatiostat

≥98% (HPLC)

• Synonym(s): γ-Glu-S-BzCys-PhGly diethyl ester, (2S)-2-Amino-5-[[(2R)-3-benzylsulfanyl-1-[[(1R)-2-ethoxy-2-oxo-1-phenylethyl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoate, TER 199, TER199, TLK199, Terrapin 199
• Empirical Formula (Hill Notation): C₂₇H₃₅N₃O₆S
• CAS Number: 168682-53-9
• Molecular Weight: 529.65
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 5 mg/mL, clear (warmed)
• storage temp.: 2-8°C
• SMILES string: S(C[C@H](NC(=O)CC[C@H](N)C(=O)OCC)C(=O)N[C@H](c2ccccc2)C(=O)OCC)Cc1ccccc1
• 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
• InChI key: GWEJFLVSOGNLSS-WPFOTENUSA-N

Description

Application

Ezatiostat has been used as glutathione S-transferase P1 (GSTP1) inhibitor:

• to study its effects on peroxiredoxin 6 (PRDX6) inhibition in neonatal rat testicular gonocytes[1]
• for the incubation of bronchial epithelial cells in proteolysis assay[2]
• to study its effects on the cystine-glutamate antiporter xCT (SLC7A11) expression in tumor cells[3]

Biochem/physiol Actions

Ezatiostat is an inhibitor of glutathione S-transferase P1-1 (GSTP1-1) with hematopoiesis-stimulating activity.

Ezatiostat is an inhibitor of glutathione S-transferase P1-1 (GSTP1-1) with hematopoiesis-stimulating activity. After intracellular de-esterification, the active form of ezatiostat binds to and inhibits GST P1-1, leading to activation of Jun kinase (JNK), a key regulator of cellular growth and differentiation of blood precursor cells, thereby restoring JNK and MAPK pathway activities and promoting MAPK-mediated cellular proliferation and differentiation. Ezatiostat promotes the proliferation and maturation of hematopoietic precursor cells, granulocytes, monocytes, erythrocytes and platelets. Ezatiostat has recently been given orphan drug designation for it for the treatment of myelodysplastic syndrome.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable