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Merck

481908

FK866 hydrochloride hydrate

The Nicotinamide Phosphoribosyltransferase Inhibitor, FK866, also referenced under CAS 658084-64-1, controls the biological activity of Nicotinamide Phosphoribosyltransferase. This small molecule/inhibitor is primarily used for Neuroscience applications.

Synonym(s):

Nicotinamide Phosphoribosyltransferase Inhibitor, FK866, (E)-N-(4-(1-Benzoylpiperidin-4-yl)butyl)-3-(pyridin-3-yl)acrylamide, NAMPT Inhibitor, APO866, NAMPTase Inhibitor I, PBEF Inhibitor I, Visfatin Inhibitor I, NAPRT Inhibitor, APO866, NAMPTase Inhibitor I, PBEF Inhibitor I, Visfatin Inhibitor I, NAPRT Inhibitor, (E)-N-(4-(1-Benzoylpiperidin-4-yl)butyl)-3-(pyridin-3-yl)acrylamide, NAMPT Inhibitor

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About This Item

Empirical Formula (Hill Notation):
C24H29N3O2
CAS Number:
658084-64-1
Molecular Weight:
391.51
MDL number:
MFCD10565943
UNSPSC Code:
51111800
NACRES:
NA.77

Product Name

Nicotinamide Phosphoribosyltransferase Inhibitor, FK866, The Nicotinamide Phosphoribosyltransferase Inhibitor, FK866, also referenced under CAS 658084-64-1, controls the biological activity of Nicotinamide Phosphoribosyltransferase. This small molecule/inhibitor is primarily used for Neuroscience applications.

SMILES string

N2(CCC(CC2)CCCCNC(=O)\C=C\c3cnccc3)C(=O)c1ccccc1

InChI

1S/C24H29N3O2/c28-23(12-11-21-8-6-15-25-19-21)26-16-5-4-7-20-13-17-27(18-14-20)24(29)22-9-2-1-3-10-22/h1-3,6,8-12,15,19-20H,4-5,7,13-14,16-18H2,(H,26,28)/b12-11+

InChI key

KPBNHDGDUADAGP-VAWYXSNFSA-N

assay

≥97% (HPLC)

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

yellow

solubility

DMSO: 100 mg/mL

shipped in

ambient

storage temp.

2-8°C

Quality Level

100

Related Categories

Disclaimer

Toxicity: Standard Handling (A)

Other Notes

Formentini, L., et al. 2009. Biochem. Pharmacol.77, 1612.
Nakahata, Y., et al. 2009. Science324, 654.
Ramsey. K.M., et al. 2009. Science324, 651.
Billington, R.A., et al. 2008. J. Biol. Chem.283, 6367.
Hasmann, M. and Schemainda, I., 2003. Cancer Res.63, 7436.

Packaging

Packaged under inert gas

Physical form

Supplied as a 50 mM (2 mg/102.17 µl) solution in DMSO.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

General description

A cell-permeable pyridinylacrylamide compound that acts as a selective, allosteric NAPRT/NAMPT (nicotinamide phosphoribosyltransferase) inhibitor (Ki = 0.4 nM for the enzyme/substrate complex; Ki′ = 0.3 nM for the free enzyme), while exhibiting no effect toward NPRT (nicotinic acid phosphoribosyltransferase) activity (82% inhibition of NAPRT activity at 10 nM vs no inhibition of NPRT activity at 1 µM in K-562 extract). FK866 treatment is shown to induce cell death by depleting NAD+ (Cat. Nos. 481911 & 481915 ) in HepG2 and NIH-3T3 cultures (by >95% after 24 h treatment of 10 nM FK866), likewise the addition of exogenous NAD+ is demonstrated to rescue NIH-3T3 and SH-SY5Y from FK866-induced NAD+-depletion and cell death.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Ariful Haque Abir et al.
Molecular metabolism, 87, 101981-101981 (2024-07-07)
The metabolism of different cells within the same microenvironment can differ and dictate physiological or pathological adaptions. Current single-cell analysis methods of metabolism are not label-free. The study introduces a label-free, live-cell analysis method assessing endogenous fluorescence of NAD(P)H and
Michelle Noble et al.
RNA (New York, N.Y.), 30(7), 839-853 (2024-04-13)
Several enzymes of intermediary metabolism have been identified to bind RNA in cells, with potential consequences for the bound RNAs and/or the enzyme. In this study, we investigate the RNA-binding activity of the mitochondrial enzyme malate dehydrogenase 2 (MDH2), which
Xiangguo Shi et al.
Science advances, 7(30) (2021-07-23)
Metabolic dysregulation underlies malignant phenotypes attributed to cancer stem cells, such as unlimited proliferation and differentiation blockade. Here, we demonstrate that NAD+ metabolism enables acute myeloid leukemia (AML) to evade apoptosis, another hallmark of cancer stem cells. We integrated whole-genome

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