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Merck

SML0612

Perifosine

≥98% (HPLC), Protein kinase B/Akt inhibitor, powder

Synonym(s):

4-[[Hydroxy(octadecyloxy)phosphinyl]oxy]-1,1-dimethyl-piperidinium inner salt, KRX-0401, Octadecyl-(1,1-dimethyl-4-piperidylio) phosphate

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About This Item

Empirical Formula (Hill Notation):
C25H52NO4P
CAS Number:
157716-52-4
Molecular Weight:
461.66
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

Perifosine, ≥98% (HPLC)

SMILES string

[P](=O)([O-])(OC1CC[N+](CC1)(C)C)OCCCCCCCCCCCCCCCCCC

InChI

1S/C25H52NO4P/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24-29-31(27,28)30-25-20-22-26(2,3)23-21-25/h25H,4-24H2,1-3H3

InChI key

SZFPYBIJACMNJV-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 10 mg/mL, clear

shipped in

wet ice

storage temp.

−20°C

Quality Level

100

Application

Perifosine has been used as an alkyl phospholipid AKT inhibitor.

Biochem/physiol Actions

Perifosine (KRX-0401) is a selective bioavailable alkylphospholipid inhibitor of protein kinase B/Akt (PKB/Akt) with anti-proliferative activity.
Perifosine (KRX-0401) is a selective bioavailable alkylphospholipid inhibitor of protein kinase B/Akt (PKB/Akt) with anti-proliferative activity. Perifosine acts on cell membranes, selectively targeting proliferating cells, inducing growth arrest and apoptosis.
Perifosine (octadecyl-(1,1-dimethyl-4-piperidylio)) is an antitumor compound. It acts at lipid rafts and stops lysosomal accumulation and mTORC1 (mammalian target of rapamycin complex 1) signaling. This drug exhibits significant antiproliferative activity in vitro and in vivo in various human cancer model systems.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
026M4724V
045M4725V
064M4730V
043M4758V

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Perifosine, a novel alkylphospholipid, inhibits protein kinase B activation.
Kondapaka SB, et al.
Molecular Cancer Therapeutics, 2(11), 1093-1103 (2003)
TUFT1 interacts with RABGAP1 and regulates mTORC1 signaling.
Kawasaki N, et al.
Cell discovery, 4(1), 1-1 (2018)
Natsumi Kawasaki et al.
Cell discovery, 4, 1-1 (2018-02-10)
The mammalian target of rapamycin (mTOR) pathway is commonly activated in human cancers. The activity of mTOR complex 1 (mTORC1) signaling is supported by the intracellular positioning of cellular compartments and vesicle trafficking, regulated by Rab GTPases. Here we showed
José M Bravo-San Pedro et al.
Cell metabolism, 30(4), 754-767 (2019-08-20)
Autophagy facilitates the adaptation to nutritional stress. Here, we show that short-term starvation of cultured cells or mice caused the autophagy-dependent cellular release of acyl-CoA-binding protein (ACBP, also known as diazepam-binding inhibitor, DBI) and consequent ACBP-mediated feedback inhibition of autophagy.

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