by Adam Le Gresley, PhD

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    In the previous lectures, we looked at enzyme inhibition, biological interactions, but just as important - the pharmacokinetic and pharmacodynamic profiles for different types of drugs and those factors which influence them. Specifically, when it comes to, for example, the pharmacokinetics, we were concerned with how lipophilicity can often lead to an enhanced first pass effect with metabolism, decreasing the amount of bioavailable drug. However, sometimes as we’ll see in this lecture, it can be used to our advantage in converting prodrugs into active drugs. So, let’s just recap about what a prodrug is. A prodrug can be defined as a compound which is inactive when administered, but gets converted to... in the body to the active form through biotransformation. This can be mediated enzymatically by those endogenous enzymes. Prodrugs are usually produced by the attachment of an active drug to something known as a promoiety through a metabolically-labile linkage. The term promoiety may sound a little bit complicated, but the reality is, if we were talking about, say, a carboxylic acid active drug then a promoiety would may just be an alcohol that we would attach to it as an ester. This ester, as you know, is a metabolically-labile linkage, which can be hydrolysed by esterases which is systemic. The prodrug must be readily converted in the body to the active form and also, the promoiety itself must not be toxic. Produgs themselves depend on endogenous enzymes to transform them to the active species and are used for many purposes including to increase absorption also or to decrease the number of side effects. So, let’s have a look at the factor of increasing lipophilicity. Some drugs have low lipophilicity, can lead to poor oral bioavailability. This is by virtue of them having poor oral absorption and absorption through the...

    About the Lecture

    The lecture Prodrugs by Adam Le Gresley, PhD is from the course Medical Chemistry. It contains the following chapters:

    • Prodrugs
    • Reducing ionisation
    • Creation of prodrug
    • Prolong duration of action

    Included Quiz Questions

    1. Enalapril is able to cross the gut wall due to masking of one of its carboxylates with an ester group
    2. Enalapril is poorly absorbed from the gastrointestinal tract due to it being highly lipophilic
    3. Enalaprilat is readily absorbed from the gastrointestinal tract by passive diffusion
    4. Enalapril contains two ionisable carboxylic acid groups in its structure
    5. None of the above

    Author of lecture Prodrugs

     Adam Le Gresley, PhD

    Adam Le Gresley, PhD

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