Penicillamine

The structure of D-penicillamine (d-PEN) is shown in Figure 10.4B where the three different donor groups should be noticed: Two hard donor atoms (amine-N and carboxylate-O) together with a soft thiolate (-SH) group making the chelate a universal drug for both soft and hard Lewis acids although with limited ion selectivity. D-PEN is water soluble and, in contrast to BAL, not inherently toxic. But the L-isomer is a vitamin-B6 antagonist and thus harmful to the organism. d-PEN has found wide application and may in most cases replace BAL, often applied simultaneously with EDTA as in the treatment of lead poisoning. It is also effective in sequestering gold and mercury. The administration of d-PEN to patients suffering from Wilson's disease is of particular interest (Section 10.6.5).

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