N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitro-2-furanyl)methanimine

DescriptionNifurtimox is manufactured by Bayer and marketed under the trade name Lampits.It is a nitrofuran derivative that was developed specifically for the treatment of American trypanosomiasis (Chagas'disease) (Packachanian, 1957). Nifurtimox is one of two drugs approved for use in treatment of Chagasdisease. It was shown to be the most active and least toxic of this group of agents in preclinical studies and was evaluated in clinical trials in the 1960s and subsequently marketed for use in Chagas’ disease in Latin America in the late 1960s and early 1970s. Although the use of nifurtimox for Chagas’ disease has decreased with the availability of benznidazole, a potentially more active and less toxic agent, there has been a resurgence of interest in and use of nifurtimox for the treatment of second-stage human African trypanosomiasis (HAT)caused by Trypanosoma brucei gambiense.

UsesAntiprotozoal (Trypanosoma). Showing anti-Trypanosoma cruzi activity.

UsesThe nitrofuran nifurtimoxis the most effective drug against T. cruzi, being cidal against the trypomastigote and amastigote forms. It is active against both the extra- and intracellular form of the parasite. In combination with corticosteroids it has prevented myocardial inflammation and destroyed the parasites within the heart. Side effects of the drug tend to be mild and include nausea, vomiting, insomnia, nervous excitation, vertigo, and skin rashes. Cardiac symptoms are treated symptomatically. Benznidazole (2, C12H12N4O3, N-benzyl-2-nitro-1 imidazoleacetamide, RO 7-1051), an alternative drug, can prevent the spread of the parasites from one tissue to another although relapses are common. Primaquine can destroy the extracellular trypanosomes in the blood, but is not effective against the intracellular forms of the parasite.

General DescriptionNifurtimox acts as a hypoxia-activated cytotoxin, which specifically kills clonogenic tumor cells under hypoxic conditions. It is used to treat Chagas disease and African trypanosomiasis. Nifurtimox inhibits neuroblastoma and medulloblastoma cell growth.