27046-19-1

Basic information

• Product Name: 4-ketocyclophosphamide
• Synonyms: 4-ketocyclophosphamide;2-[Bis(2-chloroethyl)amino]tetrahydro-4H-1,3,2-oxazaphosphorin-4-one 2-oxide;4-Oxo Cyclophosphamide;2-[Bis(2-chloroethyl)aMino]tetrahydro-
• CAS NO: 27046-19-1
• Molecular Formula: C₇H₁₃Cl₂N₂O₃P
• Molecular Weight: 275.09
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Phosphorylating and Phosphitylating Agents
• Mol File: 27046-19-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 139-141°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.42g/cm³
• Refractive Index: 1.515
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• PKA: 12.02±0.20(Predicted)
• CAS DataBase Reference: 4-ketocyclophosphamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ketocyclophosphamide(27046-19-1)
• EPA Substance Registry System: 4-ketocyclophosphamide(27046-19-1)

Safety Data

• Hazardous Substances Data: 27046-19-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

A minor metabolite of Cyclophosphamide (C988580).

InChI:InChI=1/C7H13Cl2N2O3P/c8-2-4-11(5-3-9)15(13)10-7(12)1-6-14-15/h1-6H2,(H,10,12,13)

Upstream product

• 50-18-0 cyclophosphamide 
• 593-56-6 N-methoxylamine hydrochloride 
• 51274-71-6 4-peroxycyclophosphamide 

Relevant articles and documents

4-Peroxycyclophosphamide use thereof

4-Peroxycyclophosphamide is provided along with its method of preparation. The compound is useful for treating human cancer, particularly human primary and metastatic malignant brain tumors.

Effect of damaged liver parenchyma, renal insufficiency and hemodialysis on the pharmacokinetics of cyclophosphamide and its activated metabolites

Patients with impaired liver function have a reduced biotransformation rate of the cytostatic agent cyclophosphamide. With pathologically reduced serum cholinesterase activity the half-life of the drug increases from normally 4.3 h to 6.7 h. These patients show significantly lower peak levels of activated cyclophosphamide (4-hydroxy-cyclophosphamide + aldophosphamide). Because of the low renal clearance of cyclophosphamide (16 ml/min) and equally low renal excretion of activated cyclophosphamide amounting to only 1% of the applied dose more than 80% of the drug is still metabolized and the area under the curve of activated cyclophosphamide (cXt) remains relatively constant. No change in the pharmacokinetics of cyclophosphamide and its activated metabolite is observed in an anuric patient. However, an accumulation of toxic, directly alkylating metabolites with a fourfold alkylation rate of plasma proteins is found in this case. Hemodialysis sufficiently eliminated the toxic alkylating metabolites without a measurable influence on the pharmacokinetics of activated cyclophosphamide.