Perifosine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Perifosine
Accession Number
DB06641
Description

Perifosine is a novel alkylphospholipid with antiproliferative properties attributed to protein kinase B inhibition.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 461.668
Monoisotopic: 461.363396156
Chemical Formula
C25H52NO4P
Synonyms
  • Perifosine
External IDs
  • KRX-0401
  • NSC-639966

Pharmacology

Pharmacology
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Indication

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

Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics
Not Available
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.

TargetActionsOrganism
URAC-alpha serine/threonine-protein kinaseNot AvailableHumans
UMitogen-activated protein kinase 1Not AvailableHumans
UProtein kinase C alpha typeNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
Medicalerrors
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Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic phosphoric acids and derivatives
Sub Class
Phosphate esters
Direct Parent
Dialkyl phosphates
Alternative Parents
Piperidines / Tetraalkylammonium salts / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives / Amines
Substituents
Aliphatic heteromonocyclic compound / Amine / Azacycle / Dialkyl phosphate / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organic salt / Organoheterocyclic compound
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
ammonium betaine, phospholipid (CHEBI:67272)

Chemical Identifiers

UNII
2GWV496552
CAS number
157716-52-4
InChI Key
SZFPYBIJACMNJV-UHFFFAOYSA-N
InChI
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
IUPAC Name
1,1-dimethyl-4-{[(octadecyloxy)phosphinato]oxy}piperidin-1-ium
SMILES
CCCCCCCCCCCCCCCCCCOP([O-])(=O)OC1CC[N+](C)(C)CC1

References

General References
Not Available
ChemSpider
130628
BindingDB
50431630
ChEBI
67272
ChEMBL
CHEMBL372764
Wikipedia
Perifosine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentColorectal Cancers1
3TerminatedTreatmentMultiple Myeloma (MM)1
2CompletedTreatmentAlveolar Soft Part Sarcoma (ASPS) / Chondrosarcomas / Extra Skeletal Myxoid Chondrosarcomas1
2CompletedTreatmentBrain Cancer / CNS / Gliomas, Malignant / Malignancies1
2CompletedTreatmentBreast Cancer1
2CompletedTreatmentChronic Lymphocytic Leukaemia (CLL) / Small Lymphocytic Lymphoma1
2CompletedTreatmentEndometrial Cancer / Sarcomas1
2CompletedTreatmentGastrointestinal Stromal Tumors1
2CompletedTreatmentLeukemias1
2CompletedTreatmentMalignant Lymphomas / Tumors1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000101 mg/mLALOGPS
logP3.82ALOGPS
logP3.15ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.59 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity142.15 m3·mol-1ChemAxon
Polarizability58.14 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein serine/threonine/tyrosine kinase activity
Specific Function
AKT1 is one of 3 closely related serine/threonine-protein kinases (AKT1, AKT2 and AKT3) called the AKT kinase, and which regulate many processes including metabolism, proliferation, cell survival, ...
Gene Name
AKT1
Uniprot ID
P31749
Uniprot Name
RAC-alpha serine/threonine-protein kinase
Molecular Weight
55686.035 Da
References
  1. Shome D, Trent J, Espandar L, Hatef E, Araujo DM, Song CD, Kim SK, Esmaeli B: Ulcerative keratitis in gastrointestinal stromal tumor patients treated with perifosine. Ophthalmology. 2008 Mar;115(3):483-7. doi: 10.1016/j.ophtha.2007.11.016. Epub 2008 Jan 16. [PubMed:18201764]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Rna polymerase ii carboxy-terminal domain kinase activity
Specific Function
Serine/threonine kinase which acts as an essential component of the MAP kinase signal transduction pathway. MAPK1/ERK2 and MAPK3/ERK1 are the 2 MAPKs which play an important role in the MAPK/ERK ca...
Gene Name
MAPK1
Uniprot ID
P28482
Uniprot Name
Mitogen-activated protein kinase 1
Molecular Weight
41389.265 Da
References
  1. Knowling M, Blackstein M, Tozer R, Bramwell V, Dancey J, Dore N, Matthews S, Eisenhauer E: A phase II study of perifosine (D-21226) in patients with previously untreated metastatic or locally advanced soft tissue sarcoma: A National Cancer Institute of Canada Clinical Trials Group trial. Invest New Drugs. 2006 Sep;24(5):435-9. [PubMed:16528479]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Calcium-activated, phospholipid- and diacylglycerol (DAG)-dependent serine/threonine-protein kinase that is involved in positive and negative regulation of cell proliferation, apoptosis, differenti...
Gene Name
PRKCA
Uniprot ID
P17252
Uniprot Name
Protein kinase C alpha type
Molecular Weight
76749.445 Da
References
  1. Knowling M, Blackstein M, Tozer R, Bramwell V, Dancey J, Dore N, Matthews S, Eisenhauer E: A phase II study of perifosine (D-21226) in patients with previously untreated metastatic or locally advanced soft tissue sarcoma: A National Cancer Institute of Canada Clinical Trials Group trial. Invest New Drugs. 2006 Sep;24(5):435-9. [PubMed:16528479]

Drug created on March 19, 2008 16:43 / Updated on February 21, 2021 18:52