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Merck
CN

SML4226

MK-8719

≥98% (HPLC), powder, O-GlcNAcase inhibitor

Synonym(s):

(3aR,5S,6S,7R,7aR)-5-(Difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol, MK 8719, MK8719

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About This Item

Empirical Formula (Hill Notation):
C9H14F2N2O3S
CAS Number:
Molecular Weight:
268.28
NACRES:
NA.21
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
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SMILES string

O[C@@H]1[C@]2([H])[C@](SC(NCC)=N2)([H])O[C@@H]([C@H]1O)C(F)F

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

Application

MK-8719 may be used in enzyme and cell-based assays to analyze its inhibitory effects on O-GlcNAcase activity and to assess its binding kinetics via surface plasmon resonance.

Biochem/physiol Actions

MK-8719 is an orally available, brain-penetrant, potent and selective O-GlcNAcase (OGA) inhibitor (Ki in nM = 7.9/human, 9.7/rat, 12.1/dog, 9.7/mouse) that upregulates O-linked N-acetylglucosamine (O-GlcNAc) levels both in cultures (EC50 = 52.7 nM in rat PC-12 cells) and in vivo (fold increase = 3.2 in brain and 2.2 in PBMC 8h post 10 mg/kg p.o. in rats). Chronic MK-8719 treatment ameliorates brain atrophy in human mutant tau (P301L) expressing rTg4510 mice (100 mg/kg b.i.d. p.o. from 8 to 32 weeks of age).

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hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Harold G Selnick et al.
Journal of medicinal chemistry, 62(22), 10062-10097 (2019-09-06)
Inhibition of O-GlcNAcase (OGA) has emerged as a promising therapeutic approach to treat tau pathology in neurodegenerative diseases such as Alzheimer's disease and progressive supranuclear palsy. Beginning with carbohydrate-based lead molecules, we pursued an optimization strategy of reducing polar surface
Shinichiro Matsui et al.
Leukemia, 38(5), 1032-1045 (2024-04-13)
TNF receptor associated factor 6 (TRAF6) is an E3 ubiquitin ligase that has been implicated in myeloid malignancies. Although altered TRAF6 expression is observed in human acute myeloid leukemia (AML), its role in the AML pathogenesis remains elusive. In this
Xiaohai Wang et al.
The Journal of pharmacology and experimental therapeutics, 374(2), 252-263 (2020-06-05)
Deposition of hyperphosphorylated and aggregated tau protein in the central nervous system is characteristic of Alzheimer disease and other tauopathies. Tau is subject to O-linked N-acetylglucosamine (O-GlcNAc) modification, and O-GlcNAcylation of tau has been shown to influence tau phosphorylation and

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