ABSTRACT
Mecillinam, developed by Leo Pharmaceutical Laboratories (Ballerup, Denmark), has a beta-lactam structure and is derived from the penicillin nucleus, 6-aminopenicillinic acid (6-APA). Natural and semisynthetic penicillins are acylamino-penicillinates, but mecillinam is a different penicillin, being a 6-beta-amidinopenicillanic acid, which contains a substituted amidino group (Lund and Tybring, 1972; Matsuhashi et al., 1974). Mecillinam, in its hydrochloride dihydrate form, is suitable for i.m. or i.v. administration, but it is not absorbed when given orally. A pivaloyloxymethyl ester of the drug, pivmecillinam hydrochloride, is readily absorbed from the gastrointestinal tract. After absorption, it is hydrolyzed by enzymes with the liberation of mecillinam, the active form of the drug (Roholt et al., 1975). A combination of pivmecillinam and the pivaloyl ester of ampicillin, pivampicillin, was used during the 1980s, but is not available today. The chemical structure of mecillinam is shown in Figure 11.1. Chemical structure of mecillinam (FL 1060). https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/fig11_1.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>
