Nitrogen mustards

The original mustard, mechlorethamine, was highly reactive with a half-life of minutes in biological fluids. Other members—melphalan and chlorambucil—are less chemically reactive and can be adminis tered orally. Melphalan is a derivative of nitrogen mustard and the amino acid phenylalanine. The rationale behind this was that dividing cells might take up amino acids more rapidly (and hence melphalan), thus providing some tumour selectivity.

Chlorambucil is the phenylbutyric-acid derivative of nitrogen mustard, a well-absorbed alkylating agent with activity in both solid and haematological malignancies.

CICH.CH,

2 I2

Ifosfamide

Chloroacetaldeehyde + CICH2CH2 OH dechloroethylated I I metabolites CICH2CH2 N CH

4-Hydroxy ifosfamide k

CICH CH O

2 I2 II

CICH2CH2 N CH

CH =CH-CHO

Aldoifosfamide

Acrolein

CICH2CH2

2 I2

CICH2CH2 N

CICH2CH2

CICH2CH2 N COOH

Isophosphoramide mustard Metabolism of ifosfamide.

Carboxyifosfamide

CICH2CH2

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