Talampicillin is a
beta lactamantibiotic from the
penicillin family. It is an acid stable prodrug that was administered orally. It is not approved by the FDA for use in the United States. It should be avoided in Liver diseases
Synthesis
Ampicillin remains the penicillin of choice for many infections because of its oral activity and good potency against
Gram-negative bacteria. A number of
prodrugs have been examined in attempts to improve upon the
pharmacodynamic characteristics, and one of these is talampicillin.
One synthesis involved protecting the primary amino group of
ampicillin (1) as the enamine with
ethyl acetoacetate (2). THis was then esterified by reaction with 3-bromopthalide (3), and the enamine was carefully hydrolyzed with dilute HCl in acetonitrile to produce talampicillin (4).[citation needed]