NAV

Palifosfamide

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

Identification

Generic Name
Palifosfamide
DrugBank Accession Number
DB05668
Background

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.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 221.022
Monoisotopic: 219.993519532
Chemical Formula
C4H11Cl2N2O2P
Synonyms
  • Ifosfamide mustard
  • Ifosforamide mustard
  • Isophosphamide mustard
  • Isophosphoramide mustard
  • Palifosfamide
External IDs
  • NSC-297900
  • ZIO-201
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Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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 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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
DrugInteraction
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AmbroxolThe risk or severity of methemoglobinemia can be increased when Palifosfamide is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Palifosfamide is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Palifosfamide is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Palifosfamide is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Palifosfamide is combined with Bupivacaine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Alkyl chloride / Alkyl halide / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organic phosphoric acid diamide / Organochloride / Organohalogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
phosphorodiamide (CHEBI:80566)
Affected organisms
Not Available

Chemical Identifiers

UNII
6A4U6NN813
CAS number
31645-39-3
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

References

General References
Not Available
Human Metabolome Database
HMDB0060691
KEGG Compound
C16559
ChemSpider
90740
ChEBI
80566
ChEMBL
CHEMBL889
ZINC
ZINC000001869573

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
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
2Unknown StatusTreatmentSoft Tissue Sarcoma1
1CompletedTreatmentAdvanced Malignant Neoplasm1
1SuspendedTreatmentAdvanced Malignant Neoplasm1

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-MSsplash10-05g3-6910000000-53a3ebd8119a9d7c12be
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-1900000000-f0743d675cfcaacd4a1c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-e04967e2a421bbe01c36
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03ec-9600000000-9473e5c3e52b2b4599cc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9100000000-f74e968b9f493861e3a0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-56e8b94adfb6cee9399c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-fd8a4d4dafb34ed67fdd
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-1900000000-f0743d675cfcaacd4a1c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-e04967e2a421bbe01c36
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03ec-9600000000-9473e5c3e52b2b4599cc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9100000000-f74e968b9f493861e3a0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-56e8b94adfb6cee9399c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-fd8a4d4dafb34ed67fdd
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-136.6853194
predicted
DarkChem Lite v0.1.0
[M-H]-141.69662
predicted
DeepCCS 1.0 (2019)
[M-H]-136.6853194
predicted
DarkChem Lite v0.1.0
[M-H]-141.69662
predicted
DeepCCS 1.0 (2019)
[M+H]+137.7912194
predicted
DarkChem Lite v0.1.0
[M+H]+144.60374
predicted
DeepCCS 1.0 (2019)
[M+H]+137.7912194
predicted
DarkChem Lite v0.1.0
[M+H]+144.60374
predicted
DeepCCS 1.0 (2019)
[M+Na]+136.8923194
predicted
DarkChem Lite v0.1.0
[M+Na]+153.31047
predicted
DeepCCS 1.0 (2019)
[M+Na]+136.8923194
predicted
DarkChem Lite v0.1.0
[M+Na]+153.31047
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. DNA (cytosine-5)-methyltransferase 1
Kind
Protein
Organism
Humans
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 at November 18, 2007 18:26 / Updated at January 14, 2023 19:03