Description In vitro In vivo
ChemicalBook > CAS DataBase List > (E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE

(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 (Ki = 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 (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.

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

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Shanghai Boyle Chemical Co., Ltd.
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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