Palifosfamide

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

Identification

Name
Palifosfamide
Accession Number
DB05668
Type
Small Molecule
Groups
Investigational
Description

Palifosfamide (ZIO-201) is a proprietary stabilized metabolite of ifosfamide. Ifosfamide has been shown to be effective in high doses in treating testicular cancer, sarcoma and lymphoma.

Structure
Thumb
Synonyms
Not Available
External IDs
NSC-297900 / ZIO-201
Categories
UNII
6A4U6NN813
CAS number
31645-39-3
Weight
Average: 221.022
Monoisotopic: 219.993519532
Chemical Formula
C4H11Cl2N2O2P
InChI Key
BKCJZNIZRWYHBN-UHFFFAOYSA-N
InChI
InChI=1S/C4H11Cl2N2O2P/c5-1-3-7-11(9,10)8-4-2-6/h1-4H2,(H3,7,8,9,10)
IUPAC Name
bis[(2-chloroethyl)amino]phosphinic acid
SMILES
OP(=O)(NCCCl)NCCCl

Pharmacology

Indication

Investigated for use/treatment in cancer/tumors (unspecified), lymphoma (unspecified), and sarcoma.

Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action

After metabolic activation, palifosfamide alkylates or binds with many intracellular molecular structures, including nucleic acids. The cytotoxic action is primarily due to cross-linking of strands of DNA and RNA, as well as inhibition of protein synthesis.

TargetActionsOrganism
UDNA (cytosine-5)-methyltransferase 1Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Palifosfamide.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Palifosfamide.Experimental
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Palifosfamide.Approved, Investigational, Withdrawn
BevacizumabBevacizumab may increase the cardiotoxic activities of Palifosfamide.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Palifosfamide.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Palifosfamide.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Palifosfamide.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Palifosfamide.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Palifosfamide.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Palifosfamide.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Palifosfamide.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Palifosfamide.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Palifosfamide.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Palifosfamide.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Palifosfamide.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Palifosfamide.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Palifosfamide.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Palifosfamide.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Palifosfamide.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Palifosfamide.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Palifosfamide.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0060691
KEGG Compound
C16559
ChemSpider
90740
ChEBI
80566
ChEMBL
CHEMBL889

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentCancer, Advanced1
1, 2CompletedTreatmentAdvanced Sarcoma1
2CompletedTreatmentBreast Cancer Nos Metastatic Recurrent1
2TerminatedTreatmentAdult Central Nervous System Germ Cell Tumor / Adult Teratoma / Extragonadal Seminoma / Malignant Extragonadal Germ Cell Tumor / Malignant Extragonadal Non-Seminomatous Germ Cell Tumor / Recurrent Malignant Testicular Germ Cell Tumor / Recurrent Ovarian Germ Cell Tumor / Stage IV Extragonadal Non-Seminomatous Germ Cell Tumor / Stage IV Extragonadal Seminoma / Stage IV Ovarian Germ Cell Tumor1

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 Solubility8.86 mg/mLALOGPS
logP-0.37ALOGPS
logP-0.39ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)5.43ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.36 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity46.2 m3·mol-1ChemAxon
Polarizability19 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as organic phosphoric acid diamides. These are organophosphorus compounds with the general formula RNP(R2)(O)=O (R=alkyl, aryl; R2 = amine group).
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic phosphoric acids and derivatives
Sub Class
Organic phosphoramides
Direct Parent
Organic phosphoric acid diamides
Alternative Parents
Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Alkyl chlorides
Substituents
Organic phosphoric acid diamide / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative / Organonitrogen compound / Organochloride / Organohalogen compound / Alkyl halide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
phosphorodiamide (CHEBI:80566)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Methylates CpG residues. Preferentially methylates hemimethylated DNA. Associates with DNA replication sites in S phase maintaining the methylation pattern in the newly synthesized strand, that is ...
Gene Name
DNMT1
Uniprot ID
P26358
Uniprot Name
DNA (cytosine-5)-methyltransferase 1
Molecular Weight
183163.635 Da

Drug created on November 18, 2007 11:26 / Updated on March 02, 2018 03:04