start1 - BUPROPION Chemical and trade names of drug...

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BUPROPION Chemical and trade names of drug Bupropion Wellbutrin Zyban Voxra Budeprion Aplenzin 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one Amfebutamone Proprietary names Aminoketones Structural formula and stereoisomerism C 13 H 18 Cl N O Acid/Base properties and solubility in aqueous and organic systems Referring to the chemical structure it can be seen that bupropion has a fairly hydrophilic core (benzene ring) and polar groups such as the chloro-group, amine and ketone. The amine group does increase water solubility because it is polar but more importantly it is ionisable which significantly increases the water solubility (Jamie, 2011): Bupropion has a pKa of 7.9 (O’Byrne et al., 2010). The amine on the carbon chain can act as a weak base:
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The partition coefficient (logP) equalled 3.21 : drugs that are used to target the central nervous system would have a logP value of approximately 2, therefore bupropion was designed to act elsewhere in order to avoid possible central nervous system side effects such as drowsiness (Jamie, 2011). Clinical Uses Depression: bupropion is an effective antidepressant; there have been positive responses from both bipolar and atypical depression. However its clinical efficiency is dependent on the individual (Demyttenaere and Jaspers, 2008) Anxiety: it has had an overall positive result in helping patients’ social anxiety and other anxiety brought on by depression, though in some cases it has led to increased anxiety Smoking: recognised as an effective aid to smoking cessation, bupropion does this through the modulation of dopaminergic (dopamine) and noradrenergic (norepinephrine) systems. Although bupropion is known as a relatively weak dopamine reuptake inhibitor and inhibits norepinephrine at high concentrations, its inhibition of transporter function is associated with the increase in extracellular dopamine and norepinephrine concentration which is believed to substitute for nicotine-evoked neurotransmitter releases during smoking. This inhibition mimics nicotine reinforcement and relieving withdrawal symptoms (Imad Damaj et al., 2004). Weight loss (obesity): long term use of bupropion can lead result in weight
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This note was uploaded on 04/27/2011 for the course SCIENCE 02 taught by Professor Apfd during the Spring '10 term at Alabama.

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