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Merck
CN

SML3618

KI-696

≥98% (HPLC), KEAP1 Kelch domain inhibitor, powder

Synonym(s):

(βS)​-β-​[3-​[[(4R)​-​3,​4-​Dihydro-​4-​methyl-​1,​1-​dioxido-​2H-​5,​1,​2-​benzoxathiazepin-​2-​yl]​methyl]​-​4-​methylphenyl]​-​7-​methoxy-​1-​methyl-1H-​benzotriazole-​5-​propanoic acid, (3S)-3-(7-Methoxy-1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(4-methyl-3-(((R)-4-methyl-1,1-dioxido-3,4-dihydro-2H-benzo[b]-[1,4,5]oxathiazepin-2-yl)methyl)phenyl)propanoic acid, KI 696, KI696

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About This Item

Empirical Formula (Hill Notation):
C28H30N4O6S
CAS Number:
1799974-70-1
Molecular Weight:
550.63
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD31630709

Key Documents

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Product Name

KI-696, ≥98% (HPLC)

SMILES string

[S]1(=O)(=O)N(C[C@H](Oc5c1cccc5)C)Cc2c(ccc(c2)[C@H](CC(=O)O)c3cc4nn[n](c4c(c3)OC)C)C

InChI key

ZDNGJXBUEQNFBQ-GCJKJVERSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

KI-696 is a non-cytotoxic (10 mM; BEAS-2B cells), Kelch domain-targeing (Kd ~1.3 nM) KEAP1 selective inhibitor that effectively upregulates nuclear NRF2 level in NHBE cells (%increase/[KI-696] = 100%/10 nM and 127%/100 nM; 6 hr) and NRF2 target genes transcription by blocking KEAP1-mediated NRF2 downregulation. KI-696 (5-50 mmol/kg i.v.) upregulates NRF2 target genes transcription in rat lungs in vivo, as well as alleviate ozone-induced pulmonary inflammation and GSH depletion. KI-696 inhibits OATP1B1, BSEP, and PDE3A only at much higher concentrations (IC50 = 2.5, 4.0, 10 mM, respectively) and exhibits little or no potency toward a panel of 46 channels, enzymes, and receptors.
Non-cytotoxic, selective KEAP1 Kelch domain inhibitor that effectively upregulates NRF2 actfivity in cultures and in rats in vivo.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000531297
0000531299
0000531299
0000531297
0000390780

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Thomas G Davies et al.
Journal of medicinal chemistry, 59(8), 3991-4006 (2016-04-01)
KEAP1 is the key regulator of the NRF2-mediated cytoprotective response, and increasingly recognized as a target for diseases involving oxidative stress. Pharmacological intervention has focused on molecules that decrease NRF2-ubiquitination through covalent modification of KEAP1 cysteine residues, but such electrophilic
[Treatment of acute thromboembolism in hereditary antithrombin deficiency--a review].
L Tengborn
Lakartidningen, 84(15), 1249-1251 (1987-04-08)
Patrizia Romani et al.
Nature cell biology, 24(2), 168-180 (2022-02-16)
Metastatic breast cancer cells disseminate to organs with a soft microenvironment. Whether and how the mechanical properties of the local tissue influence their response to treatment remains unclear. Here we found that a soft extracellular matrix empowers redox homeostasis. Cells

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