dehydroemetine

Definition

ChEBI: Dehydroemetine is a pyridoisoquinoline which was developed in response to the cardiovascular toxicity associated with emetine and results from the dehydrogenation of the heterotricylic ring of emetine. It is an antiprotozoal agent and displays antimalarial, antiamoebic, and antileishmanial properties. It has a role as an antiprotozoal drug, an antimalarial and an antileishmanial agent. It is a member of isoquinolines, an aromatic ether and a pyridoisoquinoline. It derives from a hydride of an emetan.

Pharmaceutical Applications

The synthetic racemic derivative of the plant alkaloid emetine. Formulated as the hydrochloride for intramuscular administration. Like the parent compound, emetine, it inhibits E. histolytica at concentrations of 1–10 mg/L in vitro, but it is more active than the parent in animal models. Drugresistance in E. histolytica is rare.
No human pharmacokinetic data are available. A halflife of 2 days, compared with 5 days for emetine, has been reported. There is selective tissue binding and accumulation in the liver, lung, spleen and kidney.
It is considerably less toxic than emetine, possibly because it is more rapidly eliminated. Nevertheless, nausea, vomiting, diarrhea and abdominal cramps frequently occur. Neuromuscular effects have also been reported. More serious cardiotoxic effects can lead to electrocardiogram (EGG) changes, tachycardia and a drop in blood pressure.
It was formerly used as a second-line treatment in severe intestinal or hepatic amebiasis, but is no longer recommended for use.