PERIFOSINE

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19216841
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serine/threonine-protein kinase AKT 29 Target ID: CHEMBL2111353 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16418332 \| https://www.ncbi.nlm.nih.gov/pubmed/19216841	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Colorectal cancer 101 Sources: https://clinicaltrials.gov/ct2/show/NCT01097018	Primary	Phase III 656	Unknown Approved Use Unknown
Multiple myeloma 159 Sources: https://clinicaltrials.gov/ct2/show/NCT01002248	Primary	Phase III 656	Unknown Approved Use Unknown
Waldenström's macroglobulinemia 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20103671	Primary	Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 60	P-gp 1537

Drug as perpetrator

Target	Modality	Activity
CYP19A1 60	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743083#sid=144206916	no
BCRP 773	supressor 155 Sources: https://pubmed.ncbi.nlm.nih.gov/33912444/	yes
P-gp 1650	supressor 155 Sources: https://pubmed.ncbi.nlm.nih.gov/18385752/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=144206916	no

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY113480	https://www.001chemical.com/chem/157716-52-4
AA Blocks	AA001PL2	https://www.aablocks.com/goods/Goods/detail?id=AA001PL2
AEchem Scientific Corp., USA	AE1-019280	http://www.aechemsc.com/info_products/AE1-019280.php
AK Scientific, Inc. (AKSCI)	W3423	http://www.aksci.com/item_detail.php?cat=W3423
Aaron Chemicals	AR001QCU	http://www.aaronchem.com/157716-52-4
AbMole Bioscience	M1823	http://www.abmole.com/products/perifosine.html
Acadechem	ACDC-061681	http://acadechemical.com/product/4034
Achemtek	0102-018263	http://www.achemtek.com/157716-52-4
Acorn PharmaTech	ACN-038217	http://www.acornpharmatech.com/
Active Biopharma	ABP000409	http://www.activebiopharma.com/157716-52-4
Adooq BioScience	Perifosine	http://www.adooq.com/perifosine.html
Alfa Chemistry	AP157716524	https://reagents.alfa-chemistry.com/product/perifosine-cas-157716-52-4-5820.html
Ambeed	A140384	https://www.ambeed.com/products/157716-52-4.html
Anward	ANW-54211	http://www.anward.com/pro_result/40662
ApexBio Technology	A8309	http://www.apexbt.com/perifosine.html
Ark Pharm	AK-48419	http://www.arkpharminc.com/products/157716-52-4.html
Ark Pharma Scientific Limited	A-0301	http://www.arkpharmtech.com/product/32252.html
AstaTech, Inc.	27712	http://www.astatechinc.com/CPSResult.php?CRNO=30569
Aurum Pharmatech LLC	S-7469	http://www.Aurumpharmatech.com/Product/ProductDetails/S_7469
Axon MedChem	1663	https://www.axonmedchem.com/product/1663
BLD Pharm	BD147314	http://www.bldpharm.com/products/157716-52-4.html
BOC Sciences	157716-52-4	https://www.bocsci.com/perifosine-cas-157716-52-4-item-84985.html
BioChemPartner	BCP00245	http://www.biochempartner.com/157716-52-4-BCP00245
BioCrick	BCC3673	http://www.biocrick.com/Perifosine-BCC3673.html
BioSynth	J-500086	https://www.biosynth.com/en/products/all-products/products/J-500086.html
CSNpharm	CSN11682	https://www.csnpharm.com/products/perifosine.html
Capot Chemical	22480	http://www.capotchem.com/en/22480.htm
Capot Chemical	PubChem22480	http://www.capotchem.com/en/22480.htm
Chem Scene	CS-0209	http://www.chemscene.com/157716-52-4.html
ChemMol	44023882	http://www.chemmol.com/chemmol/44023882.html
ChemMol	49400126	http://www.chemmol.com/chemmol/49400126.html
ChemReagents	80076261	http://www.chemreagents.com/Product/Product.asp?ProductID=80076261
ChemShuttle	101024	http://www.chemshuttle.com/catalogsearch/result/?q=157716-52-4&cat=
Chemspace	CSSB00015188292	https://chem-space.com/CSSB00015188292
Clearsynth	CS-T-60280	https://www.clearsynth.com/en/CST60280.html
Combi-Blocks	QB-2944	http://www.combi-blocks.com/cgi-bin/find.cgi?QB-2944
DC Chemicals	DC2021	http://www.dcchemicals.com/product_show-Perifosine_KRX_0401_.html
Excenen	EX-A2229	https://www.excenen.com/searchresultlist.php?id=157716-52-4
Finetech	FT-0651459	http://www.finetechnology-ind.com/prod/detail/pub/157716-52-4.html
Hairui	HR110888	http://www.hairuichem.com/en/product/137281-23-3.html
Hairui	HR109541	http://www.hairuichem.com/en/product/157716-52-4.html
Matrix Scientific	90509	https://www.matrixscientific.com/090509.html
MedChem Express	HY-50909	https://www.medchemexpress.com/Perifosine.html
MolPort	MolPort-005-943-222	https://www.molport.com/shop/molecule-link/MolPort-005-943-222
Molcore	MC113480	https://www.molcore.com/product/157716-52-4
MuseChem	I002001	https://www.musechem.com/product/I002001.html
Oakwood	91523	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=76697&ExtHyperLink=1
Renno Tech	RL02027	http://www.rennotech.com/product_show.asp?id=2276
Selleck Chemicals	S1037	http://www.selleckchem.com/products/Perifosine.html
Smolecule	S548784	http://www.smolecule.com/products/s548784
Smolecule	S794759	https://www.smolecule.com/products/s794759
THE BioTek	bt-288189	https://www.thebiotek.com/product/inhibitors/bt-288189
Tocris	6087	https://www.tocris.com/products/perifosine_6087
VladaChem	VL260816-10MG	https://www.vladachem.com/product.php?products=157716-52-4
abcr GmbH	AB436482	http://www.abcr.com/shop/en/AB436482
eNovation Chemicals	D501024	https://www.enovationchem.com/ProductDetails.asp?ProductID=D501024
eNovation Chemicals	Y0974044	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0974044
iChemical	EBD41000	http://www.ichemical.com/chemicals/cas-157716-52-4

PubMed

Title	Date	PubMed
		252160343
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	15781658
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	21267448

Patents

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.

Name

Type

Language

PERIFOSINE

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