Drugs That Inhibit Cholesterol Synthesis

Drugs of this series include clofibrate and gemfibrozil, which are derivatives of phenoxy-carboxylic acids—fibrates; probucol, which is a substituted to-mercaptophenol; and also natural compounds lovastatin, mevastatin, and their analogs. They will be examined separately because it is difficult to explain their action via the entire mechanism.

Clofibrate: Clofibrate, ethyl ether 2-(4-chloropheoxy)-i,ro-butyric acid (20.2.2), is synthesized by esterifying 2-(4-chlorophenoxy)-i,ro-butyric acid (20.2.1) with ethyl alcohol. This is synthesized in a single-stage reaction from 4-chlorophenol, acetone, and chloroform in the presence of an alkali, evidently by initial formation of chlorethone-trichloro-ieri-butyl alcohol, which under the reaction conditions is converted into (4-chlorophenoxy)trichloro-ieri-butyl ether, and further hydrolyzed to the desired acid 20.2.1, which is further esterified with ethanol in the presence of inorganic acid [6-8].

;l—^ ¿-OH + ^=O + CHCl3 -*■ Cl—^ jh—O—C"COOH

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