Structural Alert

Structurally, terodiline (Figure 11.1) and prenyla-mine (Figure 11.2) are both closely related. Introduced in the United Kingdom in the early 1960s, prenylamine is a diphenylpropyl derivative of phenylethylamine while terodiline is a diphenyl-propyl derivative of butylamine. The presence of a chiral centre in each drug gives rise to a pair of enantiomers. It is acknowledged that even a minor modification in the structure of a molecule can dramatically alter the activity of a drug, and indeed this is the basis of metabolic inactivation of most drugs. However, notwithstanding the minor structural differences between terodiline and prenylamine, it is intuitive that terodiline must have some cardiac effects since it was marketed originally as a cardioactive antianginal agent.

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