Functional Group(s) & the Structure Weak Acid(s) or Base(s) and Function of Increasing PH - Chemistry Assignment Help

Assignment Task -

Large questions 1. Pravastatin is a widely used cholesterol-lowering drug. It is a synthetic analogue of an exciting natural product discovered in recent years in certain fungi which acts by inhibiting 3-hydroxy-3-methylglutaryl coenzyme A reductase, an enzyme critical in the biosynthesis of cholesterol. It has the following structure (see right)
 

Based on your knowledge of the ability of functional groups to solubilize organic drug molecules would you predict pravastatin to be water soluble in its unionized form?

(a) Identify the functional group(s) in the structure above which are either significant weak acid(s) and/or base(s). Estimate pKa value(s).

(b) Draw a graphical profile of Partition Coefficient (chloroform/aqueous) as a function of increasing pH for this drug.

(c) How would you modify the pH of an aqueous injection solution of pravastatin such that it remains freely soluble?

(d) This drug is susceptible to hydrolysis when stored as an aqueous solution. Carefully identify the hydrolysis products assuming alkaline-catalysed hydrolysis has occurred.

(e) Is pravastatin likely to be susceptible to oxidation? Indicate why or why not this is the case. 
 

2. Explain why the antibiotic drug benzyl penicillin but not the antibiotic drug sulphapyridine forms a sodium salt in urine at pH = 5. Accordingly, based on this data alone which drug would be excreted by the kidneys more efficiently? 

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