Ifosfamide

Ifosfamide is a pivotal active pharmaceutical ingredient and certified reference standard in the industrial synthesis and quality control of this oxazaphosphorine alkylating agent. The oxazaphosphorinane ring of Ifosfamide is constructed through reaction of N-(2-chloroethyl)-N-(3-hydroxypropyl)amine with phosphorus oxychloride, followed by substitution with 2-chloroethylamine. In quality control contexts, Ifosfamide and its related impurities—including Ifosfamide Impurity A, B, E, and F—are essential analytical reference standards for impurity profiling, analytical method development, and quality control testing. As a potent cytotoxic agent and suspected carcinogen, Ifosfamide requires careful handling and is officially recognized in the USP and European Pharmacopoeia monographs. The oxazaphosphorinane scaffold of Ifosfamide serves as a versatile platform for alkylating agent development, making Ifosfamide indispensable for pharmaceutical manufacturers and analytical laboratories.

Product Parameters

Application

For the treatment of malignant lymphoma, lung cancer, breast cancer, esophageal cancer, bone and soft tissue sarcoma, non-small cell lung cancer, head and neck cancer, cervical cancer, etc.

Synthetic Route

The general procedure for synthesizing ifosfamide using the compound (CAS: 29102-47-4) as the raw material is as follows:

Example V: To a stirred solution of 2-ethyleneimino-2-oxo-3-(2-chloroethyl)-1,3,2-oxazaphosphorinane, a solution of 2-oxaphosphorinane (1.12 g, 5.0 mM) in chloroform (12 mL) is slowly added dropwise at room temperature, followed by the dropwise addition of 3% aqueous hydrogen chloride solution (6 mL, 5.0 mM). The reaction mixture is continuously stirred for 15 minutes, after which the organic layer is separated. The aqueous layer is extracted with chloroform (2 × 6 mL). All organic layers are combined and dried over anhydrous MgSO4. The solvent is removed under reduced pressure to obtain a residue. The residue is crystallized from an ether-n-pentane mixed solvent to afford 1.02 g of crystalline product, melting point 45-46 °C, yield 78%.31P NMR (CHCl3) δ: 11.3 ppm.Mass spectrometry data: m/e 262 (0.3%), 260 (0.3%), 260 (0.8%), 213 (37%), 211 (100%.

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