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Perifosine

Perifosine structure

CAS No:
157716-52-4
Formula:
C25H52NO4P
Chemical Name:
Perifosine
Synonyms:
Piperidinium,4-[[hydroxy(octadecyloxy)phosphinyl]oxy]-1,1-dimethyl-,inner salt;D 21266;Perifosine;NSC 639966;KRX 0401;(1,1-Dimethylpiperidin-1-ium-4-yl) octadecyl phosphate
Categories:
Biochemical Engineering > Inhibitors

Description

Perifosine is an oral Akt inhibitor. All cells are sensitive to the antiproliferative properties of Perifosine with an IC50 of ~0.6-8.9 μM.

Perifosine is a phospholipid consisting of 1,1-dimethylpiperidinium-4-yl hydrogen phosphate in which the hydrogen is replaced by a stearyl (octadecyl) group. It has a role as an EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor. It is a phospholipid and an ammonium betaine. It derives from an octadecan-1-ol.|Perifosine is a novel alkylphospholipid with antiproliferative properties attributed to protein kinase B inhibition.|Perifosine is an orally active alkyl-phosphocholine compound with potential antineoplastic activity. Targeting cellular membranes, perifosine modulates membrane permeability, membrane lipid composition, phospholipid metabolism, and mitogenic signal transduction, resulting in cell differentiation and inhibition of cell growth. This agent also inhibits the anti-apoptotic mitogen-activated protein kinase (MAPK) pathway and modulates the balance between the MAPK and pro-apoptotic stress-activated protein kinase (SAPK/JNK) pathways, thereby inducing apoptosis. Perifosine has a lower gastrointestinal toxicity profile than the related agent miltefosine. (NCI04)

Perifosine Basic Attributes

Molecular Weight：

461.663

Exact Mass：

461.363403

EC Number：

1592732-453-0

UNII：

2GWV496552

NSC Number：

639966

DSSTox ID：

DTXSID3048946

NCI Thesaurus Code：

C1727

HScode：

2933399090

Characteristics

PSA：

58.6

XLogP3：

8.3

Appearance：

white to beige

Melting Point：

271-272° (dec)

Water Solubility：

H2O: soluble10mg/mL, clear

Storage Conditions：

-20°C

Safety Information

Transport codes：

NONH for all modes of transport

Precautionary statement(s)：

P201, P202, P260, P263, P264, P270, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P314, P321, P330, P332+P313, P337+P313, P362, P405, P501

Hazard Statements：

H302

GHS Classification：

|Danger|H302 (90.91%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P263, P264, P270, P280, P281, P301+P312, P305+P351+P338, P308+P313, P314, P330, P337+P313, P405, and P501|Aggregated GHS information provided by 11 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Investigated for use/treatment in solid tumors, multiple myeloma, leukemia (unspecified), lung cancer, and brain cancer.

Mechanism of Action：

Targeting cellular membranes, perifosine modulates membrane permeability, membrane lipid composition, phospholipid metabolism, and mitogenic signal transduction, resulting in cell differentiation and inhibition of cell growth. This agent also inhibits the anti-apoptotic mitogen-activated protein kinase (MAPK) pathway and modulates the balance between the MAPK and pro-apoptotic stress-activated protein kinase (SAPK/JNK) pathways, thereby inducing apoptosis.

MeSH Entry Terms：

D 21266

Perifosine Use and Manufacturing

Uses

An alkylphospholipid which inhibits Akt activation and the anti-apoptotic MAPK pathway.

Use Classification：

Human drugs -> Rare disease (orphan)

Computed Properties

Molecular Weight:461.7
XLogP3:8.3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:20
Exact Mass:461.36339614
Monoisotopic Mass:461.36339614
Topological Polar Surface Area:58.6
Heavy Atom Count:31
Complexity:454
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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