Palifosfamide
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Palifosfamide
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CAS No:
31645-39-3
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Formula:
C4H11Cl2N2O2P
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Chemical Name:
Palifosfamide
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Synonyms:
Ifosforamide mustard;N,N'-Di-(2-chloroethyl)phosphorodiamidic acid;N,N'-BIS(2-CHLOROETHYL)PHOSPHORODIAMIDATE;Isophosphamide mustard;palifosfamide;N,N'-Bis(2-chloroethyl)phosphorodiamidic acid;ZIO-201, >98%;Abbreviation: IPM-lysine
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CAS No:
Description
Palifosfamide is a novel DNA alkylator and the active metabolite of ifosfamide, with antitumor activity.
Isophosphamide mustard is a phosphorodiamide.|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.|Palifosfamide is a synthetic mustard compound with potential antineoplastic activity. An active metabolite of ifosfamide covalently linked to the amino acid lysine for stability, palifosfamide irreversibly alkylates and cross-links DNA through GC base pairs, resulting in irreparable 7-atom inter-strand cross-links; inhibition of DNA replication and cell death follow. Unlike ifosfamide, this agent is not metabolized to acrolein or chloroacetaldehyde, metabolites associated with bladder and CNS toxicities. In addition, because palifosfamide does not require activation by aldehyde dehydrogenase, it may overcome the tumor resistance seen with ifosfamide.
Palifosfamide is an active metabolite of the DNA alkylating agent ifosfamide. It is formed through hydroxylation of ifosfamide by various hepatic cytochrome P450 (CYP) isoforms. It is cytotoxic to L1210 and CCRF-CEM cancer cells when used at a concentration of 100 μM. Palifosfamide (100 mg/kg per day) reduces tumor growth in murine Lewis lung carcinoma and L1210 leukemia models, as well as a rat Yoshida ascitic sarcoma model.
ChEBI: Palifosfamide, also known as Isophosphamide mustard, is a type of phosphorodiamide. It is a proprietary stabilized metabolite of ifosfamide. Ifosfamide has been shown to be effective in high doses in treating testicular cancer, sarcoma and lymphoma.
Characteristics
61.4
-1.05
1.411
106-107 ºC
341.5±52.0 °C(Predicted)
160.4±30.7 °C
1.498
0.79±0.50(Predicted)
Store at -20°C, protect from light, stored under nitrogen
Drug Information
Investigated for use/treatment in cancer/tumors (unspecified), lymphoma (unspecified), and sarcoma.
A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)
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.
ifosfamide mustard
Computed Properties
Molecular Weight:221.02
XLogP3:-0.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:219.9935200
Monoisotopic Mass:219.9935200
Topological Polar Surface Area:61.4
Heavy Atom Count:11
Complexity:134
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
