(±)-Terodiline, the antianginal agent, perhaps represents the best authenticated example of a drug that had to be withdrawn from the world market as consequence of proven stereospecific toxicity. Terodiline has a close similarity to prenylamine from a structural and pharmacological view point. It was firs marketed as an antianginal agent but it exhibited urinary retention …
(±)-Prenylamine, an antianginal agent, was introduced in the market since early 1960. Reports associating Prenylamine with prolongation of the QT interval, ventricular tachycardia, and ventricular fibrillation started to appear. Some of these events had a fatal outcome and the drug was withdrawn from the market world-wide in 1988. Chirality and drug withdrawals Prenylamine is chemically …
Dilevalol is the (R,R)-diastereoisomer of labetalol. Labetalol has been in clinical use since 1977 for the treatment of hypertension. Labetalol is an adrenergic antagonist used to treat high blood pressure. It has a role as an antihypertensive agent, a sympatholytic agent, an alpha-adrenergic antagonist and a beta-adrenergic antagonist. Chirality and drug withdrawals Labetalol has two stereogenic …
Thalidomide was a racemic therapeutic and prescribed to pregnant women to control nausea and vomiting. The drug was withdrawn from world market when it became evident that the use in pregnancy causes phocomelia (clinical conditions where babies are born with deformed hand and limbs). Later in late 1970s, the thalidomide enantiomers were separated and enantioselective …