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N,N′-Bis(2-chloroethyl)phosphorodiamidic acid

N,N′-Bis(2-chloroethyl)phosphorodiamidic acid structure

CAS No:
31645-39-3
Formula:
C4H11Cl2N2O2P
Chemical Name:
N,N′-Bis(2-chloroethyl)phosphorodiamidic acid
Synonyms:
Phosphorodiamidic acid,N,N′-bis(2-chloroethyl)-;N,N′-Bis(2-chloroethyl)phosphorodiamidic acid;N1,N2-Bis(2-chloroethyl)phosphoric acid diamide;N,N′-Di(2-chloroethyl)phosphorodiamidic acid;Isophosphoramide mustard;Ifosfamide mustard;NSC 297900;ZIO 201;IPM;Palifosfamide;131636-51-6

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.

N,N′-Bis(2-chloroethyl)phosphorodiamidic acid Basic Attributes

Molecular Weight：

221.018

Exact Mass：

221.02

UNII：

6A4U6NN813

NSC Number：

297900

NCI Thesaurus Code：

C66990

Characteristics

PSA：

61.4

XLogP3：

-1.05

Density：

1.4±0.1 g/cm3

Melting Point：

106-107 °C

Boiling Point：

341.5±52.0 °C at 760 mmHg

Flash Point：

160.4±30.7 °C

Refractive Index：

1.498

Drug Information

Drug Indication：

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

MeSH：

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.)

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.

MeSH Entry Terms：

ifosfamide mustard

N,N′-Bis(2-chloroethyl)phosphorodiamidic acid Use and Manufacturing

Use Classification：

Human drugs -> Rare disease (orphan)

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

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Palifosfamide

CAS No.: 31645-39-3

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Guide of N,N′-Bis(2-chloroethyl)phosphorodiamidic acid

Description
Basic Attributes
Characteristics
Drug Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
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N,N′-Bis(2-chloroethyl)phosphorodiamidic acid

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