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Ezatiostat

SIGMA/SML1081 - ≥98% (HPLC)

Synonym: 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

CAS Number: 168682-53-9
Empirical Formula (Hill Notation): C27H35N3O6S
Molecular Weight: 529.65
Linear Formula: C27H35N3O6S
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-SML1081-5MG 5 mg
 $132.00
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45-SML1081-25MG 25 mg
 $535.00
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assay ≥98% (HPLC)
color white to beige
form powder
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
Quality Level 100 
solubility DMSO: 5 mg/mL, clear (warmed)
storage temp. 2-8°C
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
• for the incubation of bronchial epithelial cells in proteolysis assay
• to study its effects on the cystine-glutamate antiporter xCT (SLC7A11) expression in tumor cells
Biochem/physiol Actions: 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.
Packaging: 5, 25 mg in glass bottle
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥98% (HPLC)
Storage Temp. 2-8°C
UNSPSC 12352200

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