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Details

Stereochemistry ACHIRAL
Molecular Formula C25H52NO4P
Molecular Weight 461.6584
Optical Activity NONE
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERIFOSINE

SMILES

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

InChI

InChIKey=SZFPYBIJACMNJV-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Perifosine is an orally active alkyl-phosphocholine compound with potential antineoplastic activity. Perifosine is an Akt inhibitor, which targets the pleckstrin homology domain of Akt, thereby preventing its translocation to the plasma membrane. Perifosine exerts Akt-dependent and Akt-independent effects, and although many preclinical studies have documented Akt inhibition by perifosine, clinical validation of these findings is lacking. Perifosine is in phase II and III clinical trials for the treatment of neuroblastoma, glioblastoma multiforme and other solid tumors.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
763 ng/mL
100 mg single, oral
PERIFOSINE blood
Homo sapiens
3691 ng/mL
800 mg single, oral
PERIFOSINE blood
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
98016 ng × h/mL
100 mg single, oral
PERIFOSINE blood
Homo sapiens
398084 ng × h/mL
800 mg single, oral
PERIFOSINE blood
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
100.3 h
100 mg single, oral
PERIFOSINE blood
Homo sapiens
81 h
800 mg single, oral
PERIFOSINE blood
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
50 mg once daily
Route of Administration: Oral
In Vitro Use Guide
Growth inhibitoy activities of Perifosine against selected human cell lines appeared to be slightly more potent than activity of miltefosine. Thus, IC50s of Perifosine for melanoma cell lines M14 and SK-NEL-28 were 2.6 uM/ml and 19.9 uM/ml respectively; for CNS cell line SF-295 – 3.1 uM/ml; for prostate cell line PC-3 – 1.5 uM/ml; for Colon cell lines KM12, HT29, HCT-116 – 0.2 uM/ml, 4.0 uM/ml and 10.2 uM/ml respectively.