(E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE

Description In vitro In vivo

Product Name: (E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE
CAS No.: 658084-64-1
Chemical Name: (E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE
Synonyms: FK867;FK 866;CS-973;APO-866;K 22.175;Daporinad;FK866, >=98%;(E)-Daporinad;FK866 (APO866);FK866 (Daporinad)
CBNumber: CB62454096
Molecular Formula: C24H29N3O2
Formula Weight: 391.51
MOL File: 658084-64-1.mol

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(E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE Property

Boiling point:: 629.9±51.0 °C(Predicted)
Density: 1.131
storage temp.: -20°C
solubility: DMSO: soluble10mg/mL, clear
pka: 14.12±0.46(Predicted)
form: Yellow liquid
color: white to beige
InChIKey: KPBNHDGDUADAGP-VAWYXSNFSA-N

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Safety

Hazard Codes: Xn
Risk Statements: 22
WGK Germany: 3
HS Code: 2933399990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: F8557
Product name: FK866 hydrochloride hydrate
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $155
Updated: 2024/03/01

Sigma-Aldrich

Product number: 481908
Product name: Nicotinamide Phosphoribosyltransferase Inhibitor, FK866
Packaging: 2mg
Price: $159
Updated: 2024/03/01

Cayman Chemical

Product number: 13287
Product name: FK-866
Purity: ≥98%
Packaging: 5mg
Price: $90
Updated: 2024/03/01

Cayman Chemical

Product number: 13287
Product name: FK-866
Purity: ≥98%
Packaging: 10mg
Price: $189
Updated: 2023/06/20

Sigma-Aldrich

Product number: F8557
Product name: FK866 hydrochloride hydrate
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $613
Updated: 2024/03/01

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(E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE Chemical Properties,Usage,Production

Description

Daporinad (FK866, APO866) effectively inhibits nicotinamide phosphoribosyltransferase (NMPRTase) with IC50 of 0.09 nM in a cell-free assay. Phase 1/2.

In vitro

APO866 at low concentrations ranging from 0.09-27 nM induces dose-dependent cytotoxicity in 41 hematologic malignant cells including acute myeloid leukemia [AML], acute lymphoblastic leukemia [ALL], mantle cell lymphoma [MCL], chronic lymphocytic leukemia [CLL], and T-cell lymphoma. APO866 at low concentrations ranging from 0-10 nM induces cell death, this effect is independent of caspase activation but is associated with depolarization of mitochondrial membrane. APO866 at concentrations ranging from 0-10 nM dose-dependently induces depletion of intracellular NAD and ATP contents and cell death in various hematologic cancer cells. APO866 at concentration of 10 nM inhibits PBEF-induced secretion of MMP-3, CCL2, and CXCL8 in HFFF2 cells.

In vivo

APO866 administered intraperitoneally at dose of 20 mg/kg twice a day for 4 days, repeat weekly over 3 weeks, prevents and abrogats tumor growth in C.B.-17 SCID mice xenograft models of human AML, lymphoblastic lymphoma, and leukemia. APO866 at dose of 0.12 mg/kg/hour prevents joint destruction and leukocyte infiltration through inhibition of PBEF in mice with CIA.

Description

FK-866 is a highly specific non-competitive inhibitor of Nampt (K_i = 0.4 nM), causing gradual NAD⁺ depletion. In HepG2 human liver carcinoma cells, NAD⁺ depletion by FK-866 directs delayed cell death by apoptosis (IC₅₀ = ~1 nM). In normal human smooth muscle cells, FK-866 causes premature senescence, an effect that may be linked to decreased activity of the NAD⁺-dependent enzyme SIRT1. Also, FK-866 induces autophagy in SH-SY5Y neuroblastoma cells, as indicated by the formation of LC3-positive vesicles.

Uses

FK866 hydrochloride hydrate has been used:

to investigate its effects on intra-axonal NAD⁺ levels
to induce NAD+ depletion
to reduce the level of tumor necrosis factor-α (TNF-α), nicotinamide phosphoribosyltransferase (NAMPT) and interleukin-6 (IL-6) in the ischemic brain tissue

Definition

ChEBI: FK-866 is a member of benzamides and a N-acylpiperidine.

General Description

A cell-permeable pyridinylacrylamide compound that acts as a selective, allosteric NAPRT/NAMPT (nicotinamide phosphoribosyltransferase) inhibitor (K_i = 0.4 nM for the enzyme/substrate complex; K_i^′ = 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.

Biochem/physiol Actions

FK866 is a potent inhibitor of NAD biosynthesis, and a specific inhibitor of NAMPT (Nicotinamide Phosphoribosyltransferase, visfatin, PBEF). NAMPT functions as an intra-cellular and extra-cellular NAD biosynthetic enzyme that is important for regulating metabolism and stress resistance through sirtuins and other NAD-consuming regulators. NAMPT also acts as a cytokine independent of its enzymatic activity, playing a major part in regulating immune responses.

target

NAMPT

References

[1] nahimana a, attinger a, aubry d, greaney p, ireson c, thougaard av, tjørnelund j, dawson km, dupuis m, duchosal ma. the nad biosynthesis inhibitor apo866 has potent antitumor activity against hematologic malignancies. blood. 2009 apr 2; 113 (14): 3276-86.

(E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from (E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE manufacturers

Career Henan Chemical Co

Product: (E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE 658084-64-1
Price: US $2.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 100kg
Release date: 2018-12-23

658084-64-1, (E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDERelated Search:

Benoxinate Hydrochloride 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE Dabrafenib Trametinib Crizotinib Irinotecan Olaparib FK866 (APO866, Daporinad)

(E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE

2-PROPENAMIDE, N-[4-(1-BENZOYL-4-PIPERIDINYL)BUTYL]-3-(3-PYRIDINYL)-, (2E)-

APO-866

K 22.175

(2E)-N-[4-(1-Benzoyl-4-piperidinyl)butyl]-3-(3-pyridinyl)-2-propenamide

FK 866

FK866 (APO866)

FK866, >=98%

FK866 (APO866, Daporinad)

Daporinad

(2E)-N-[4-(1-Benzoyl-4-piperidinyl)butyl]-3-(3-pyridinyl)-2-propenamide APO 866 FK 866

APO 866 FK 866

FK866 hydrochloride hydrate

FK866 (Daporinad)

FK 866 hydrochloride

Nicotinamide Phosphoribosyltransferase Inhibitor, FK866

Daporinad (FK866)

FK867

APO866, Daporinad

(E)-Daporinad

Nicotinamide Phosphoribosyltransferase Inhibitor, FK866 - CAS 658084-64-1 - Calbiochem

FK 866 - Daporinad | APO 866

FK 866 hydrochloride - K 22.175 hydrochloride

FK-866;AP-O866;FK 866;AP O866

CS-973

Daporinad(FK866,APO866)

(E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE USP/EP/BP

Daporinad (APO866)

inhibit,Visfatin,(E) Daporinad,Autophagy,Nicotinamide phosphoribosyl transferase,NAMPT,APO-866,PBEF,FK 866,Inhibitor,Pre-B cell colony enhancing factor,APO 866,(E)-Daporinad,FK-866,(E)Daporinad

(2E)-N-4-(1-Benzoyl-piperidin-4-yl)butyl-3-(pyridin-3-yl)-acrylamide

658084-64-1

568084-64-1

Inhibitors

Inhibitor