Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

Safety Information

SML0843

Sigma-Aldrich

ISRIB

≥98% (HPLC), powder, integrated stress response inhibitor

Synonym(s):

Integrated Stress Response inhibitor, trans-N,N′-(Cyclohexane-1,4-diyl)bis(2-(4-chlorophenoxy)acetamide, trans-N,N′-1,4-Cyclohexanediylbis[2-(4-chlorophenoxy)-acetamide

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C22H24Cl2N2O4
CAS Number:
1597403-47-8
Molecular Weight:
451.34
UNSPSC Code:
12352200
PubChem Substance ID:
329825607
NACRES:
NA.77

product name

ISRIB, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 1 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

ClC1=CC=C(OCC(N[C@@H]2CC[C@@H](NC(COC3=CC=C(Cl)C=C3)=O)CC2)=O)C=C1

InChI

1S/C22H24Cl2N2O4/c23-15-1-9-19(10-2-15)29-13-21(27)25-17-5-7-18(8-6-17)26-22(28)14-30-20-11-3-16(24)4-12-20/h1-4,9-12,17-18H,5-8,13-14H2,(H,25,27)(H,26,28)/t17-,18-

InChI key

HJGMCDHQPXTGAV-IYARVYRRSA-N

Application

ISRIB (integrated stress response inhibitor) has been used as an inhibitor of integrated stress response.

Biochem/physiol Actions

ISRIB (integrated stress response inhibitor) as a drug, imparts resistance to the cells against the downstream effects of eukaryotic initiation factor 2 (eIF2)α phosphorylation such as activating transcription factor 4 (ATF4) and eukaryotic translation initiation factor 4E (eIF4E)-binding protein 1 (4E-BP1) induction.
ISRIB is a blood- brain barrier penetrant, potent and selective inhibitor of integrated stress response (ISR) that impairs adaptation to ER stress. ISRIB is a potent inhibitor of PERK signaling, which potently reverses the effects of eIF2a phosphorylation and restores the cells translation capacity. ISRIB enhances cognitive memory in rodents.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SML0843-BULK:
SML0843-25MG:
SML0843-5MG:
SML0843-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Ting Zhang et al.
The Journal of pharmacology and experimental therapeutics, 378(3), 197-206 (2021-07-04)
Phosphorylation of the eukaryotic translation initiation factor 2 α-subunit, which subsequently upregulates activating transcription factor 4 (ATF4), is the core event in the integrated stress response (ISR) pathway. Previous studies indicate phosphorylation of eukaryotic translation initiation factor 2 ɑ-subunit in
B Balakrishnan et al.
Biochimica et biophysica acta. Molecular basis of disease, 1865(11), 165516-165516 (2019-07-31)
Loss of galactose-1 phosphate uridylyltransferase (GALT) activity in humans results in Classic Galactosemia, and the GalT-deficient (GalT-/-) mouse mimics the patient condition. GalT-/- ovaries display elevated endoplasmic reticulum (ER) stress marker, BiP, and downregulated canonical phosphatidylinositol 3-kinase (Pi3k)/protein kinase B
Z D Kabir et al.
Molecular psychiatry, 22(8), 1096-1109 (2017-06-07)
CACNA1C, encoding the Ca
Caitlin M Rodriguez et al.
Nature neuroscience, 23(3), 386-397 (2020-02-19)
Repeat-associated non-AUG-initiated translation of expanded CGG repeats (CGG RAN) from the FMR1 5'-leader produces toxic proteins that contribute to neurodegeneration in fragile X-associated tremor/ataxia syndrome. Here we describe how unexpanded CGG repeats and their translation play conserved roles in regulating
Joni Vanneste et al.
Biomedicines, 10(5) (2022-05-29)
Stress granules are non-membrane bound granules temporarily forming in the cytoplasm in response to stress. Proteins of the nucleocytoplasmic transport machinery were found in these stress granules and it was suggested that stress granules contribute to the nucleocytoplasmic transport defects
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service