Ho

HO-CH2-CH2-SH ->■ HO S -»- O S ->■ O SO2

CH3 CH3 ch3'

Nifurtimox is the drug of choice for acute forms of the South American form of try-panosomiasis (Chagas disease). It is believed that the drug acts by forming a reactive radical (superoxide, hydroperoxide, hydroxyl) in the parasite, which leads to a loss of catalysis and glutathione peroxidase, and an increase in sensitivity to hydrogen peroxide, which alters its normal vital activities. Synonyms of this drug are lampit and others.

Suramin: Suramin, a hexasodium salt of [8,8' carbonyl-to-[imino-3,1-phenylencar-bonylimino(4-methyl-3,1-phenylen)carbonylimino]]-to-1,3,5-naphthalintrisulfonic acid (37.4.13), can be made by reacting 1-aminonaphthalene-3,6,8-trisulfonic acid with 4-methyl-3-nitrobenzoyl chloride to make a nitrobenzoic derivative (37.4.8). The nitro group in this compound is reduced by activated iron to an amino derivative (37.4.9), which is acylated by m-nitrobenzoylchloride to make a new nitroderivative, m-nitroben-zoyl-(4-methyl-3-aminobenzoyl)-1-aminonaphthalene-3,6,8-trisulfonic acid (37.4.10). This is once again reduced to the amine (37.4.11) in the same manner. Reacting the resulting product with phosgene makes [8,8'-carbonyl-fe-[imino-3,1-phenylencar-bonylimino(4-methyl-3,1-phenylen]-carbonylimino]-to-1,3,5-naphthalenetrisulfonic acid (37.4.12), which upon being treated with sodium hydroxide gives suramin [60-63].

ho3s

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