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Details

Stereochemistry ACHIRAL
Molecular Formula C4H11Cl2N2O2P
Molecular Weight 221.022
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PALIFOSFAMIDE

SMILES

OP(=O)(NCCCl)NCCCl

InChI

InChIKey=BKCJZNIZRWYHBN-UHFFFAOYSA-N
InChI=1S/C4H11Cl2N2O2P/c5-1-3-7-11(9,10)8-4-2-6/h1-4H2,(H3,7,8,9,10)

HIDE SMILES / InChI

Molecular Formula C4H11Cl2N2O2P
Molecular Weight 221.022
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Palifosfamide or ZIO-201 (isophosphoramide mustard; IPM), a bi-functional DNA alkylator, is the active metabolite of ifosfamide (IFOS). IFOS and the related drug cyclophosphamide (CPA) are widely used anti-cancer drugs. Both are pro-drugs and need to be metabolized to be active. Their clinical use is limited by the toxicity associated with some of their metabolites. Palifosfamide has shown efficacy in diverse cancer models. ZIOPHARM Oncology Inc, under license from Dekk-Tec Inc, was developing palifosfamide, a formulation of isophosphoramide mustard with tris(hydroxymethyl)aminomethane salt-stabilization (palifosfamide-tris) and previously with lysine-stabilization (palifosfamide-lys). Preclinical studies and phase I and I/II clinical trials demonstrated that palifosfamide-tris had an antitumor efficiency comparable or superior to that of ifosfamide. To date ZIO-201 is not present in ZIOPHARM pipeline.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Palifosfamide, a bifunctional alkylator for the treatment of sarcomas.
2010 Jan
The fate of new fosfamides in phase III studies in advanced soft tissue sarcoma.
2017 Oct
Patents

Sample Use Guides

PICASSO III: A Phase III, Placebo-Controlled Study of Doxorubicin With or Without Palifosfamide in Patients With Metastatic Soft Tissue Sarcoma. Patients were randomly assigned 1:1 to receive doxorubicin 75 mg/m2 intravenously day 1 plus palifosfamide 150 mg/m2/d intravenously days 1 to 3 or doxorubicin plus placebo once every 21 days for up to six cycles. The primary end point was progression-free survival (PFS) by independent radiologic review.
Route of Administration: Intravenous
Palifosfamide lysine was cytotoxic against all the osteosarcome cell lines tested with the IC(50) ranging from 0.5 to 1.5 microg/ml except for OS222, which had an IC(50) of 7 microg/ml.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:18:07 UTC 2023
Edited
by admin
on Sat Dec 16 16:18:07 UTC 2023
Record UNII
6A4U6NN813
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PALIFOSFAMIDE
INN   MART.   USAN   WHO-DD  
INN   USAN  
Official Name English
IFOSFAMIDE MUSTARD
Common Name English
Palifosfamide [WHO-DD]
Common Name English
PALIFOSFAMIDE [MART.]
Common Name English
IPM
Code English
palifosfamide [INN]
Common Name English
ZIO-201
Code English
PHOSPHORODIAMIDIC ACID, N,N'-BIS(2-CHLOROETHYL)-
Common Name English
N,N'-BIS(2-CHLOROETHYL)PHOSPHORODIAMIDIC ACID
Systematic Name English
ISOPHOSPHAMIDE MUSTARD
Common Name English
PALIFOSFAMIDE [USAN]
Common Name English
NSC-297900
Code English
Classification Tree Code System Code
NCI_THESAURUS C697
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
EU-Orphan Drug EU/3/08/584
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
FDA ORPHAN DRUG 257508
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
Code System Code Type Description
DRUG BANK
DB05668
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
PRIMARY
SMS_ID
100000137495
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
PRIMARY
NCI_THESAURUS
C66990
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
PRIMARY
PUBCHEM
100427
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
PRIMARY
EPA CompTox
DTXSID90865605
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
PRIMARY
ChEMBL
CHEMBL889
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
PRIMARY
INN
9003
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
PRIMARY
CAS
31645-39-3
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
PRIMARY
EVMPD
SUB75788
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
PRIMARY
USAN
TT-84
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
PRIMARY
NSC
297900
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
PRIMARY
FDA UNII
6A4U6NN813
Created by admin on Sat Dec 16 16:18:07 UTC 2023 , Edited by admin on Sat Dec 16 16:18:07 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
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PARENT -> METABOLITE ACTIVE
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ACTIVE MOIETY