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Details

Stereochemistry ACHIRAL
Molecular Formula C25H52NO4P
Molecular Weight 461.6584
Optical Activity NONE
Defined Stereocenters 0 / 0
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
Curator's Comment: description was created based on several sources, including: https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=43408 | http://adisinsight.springer.com/drugs/800005360

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

Curator's Comment: Known to be CNS penetrant in a non-human primate model. Human data not available.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Coadministration of histone deacetylase inhibitors and perifosine synergistically induces apoptosis in human leukemia cells through Akt and ERK1/2 inactivation and the generation of ceramide and reactive oxygen species.
2005 Mar 15
Perifosine and CCI 779 co-operate to induce cell death and decrease proliferation in PTEN-intact and PTEN-deficient PDGF-driven murine glioblastoma.
2011 Jan 18
Patents

Sample Use Guides

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.
Name Type Language
PERIFOSINE
INN   MI   WHO-DD  
INN  
Official Name English
NSC-639966
Code English
PERIFOSINE [MI]
Common Name English
KRX-0401
Code English
1,1-DIMETHYLPIPERIDINIUM-4-YL OCTADECYL PHOSPHATE, INNER SALT
Common Name English
perifosine [INN]
Common Name English
Perifosine [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2188
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
EU-Orphan Drug EU/3/10/740
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
FDA ORPHAN DRUG 310010
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
FDA ORPHAN DRUG 290909
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
NCI_THESAURUS C2089
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
Code System Code Type Description
INN
7645
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
NCI_THESAURUS
C1727
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL372764
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
WIKIPEDIA
PERIFOSINE
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
MESH
C105905
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
PUBCHEM
148177
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
MERCK INDEX
m8550
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID3048946
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
CHEBI
67272
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
CAS
157716-52-4
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
NSC
639966
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
SMS_ID
100000082773
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
DRUG BANK
DB06641
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
EVMPD
SUB09728MIG
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY
FDA UNII
2GWV496552
Created by admin on Fri Dec 15 16:02:24 GMT 2023 , Edited by admin on Fri Dec 15 16:02:24 GMT 2023
PRIMARY