Benzylpenicillin acetoxymethyl ester

Pcnamecillilt. 3,3-Di methyl-7-oxo-6-[(phenylace-tyl)amino]-4-thla-l-azabicyclo[3.2.0]heptane-2-ca rboxy lie acid (acetyloxyfmeihyl ester penicillin G hydroxymethyl ester acetate acetoxymethyl benzylpenicillinate benzylpenicillin acetoxymethyl ester Wy-20788 Havapen. C.,HKN,06S mol wt 406.48. C 56.14%. H 5.46%, N 6.89%, 6 23.62%, S 7.89%. Semi-synthetic antibiotic related to penicillin. Prepn Jansen, Russell. J. Chem. Soc. 1965, 2127 eidem, Brit. pat. 1,083,479 corresp to U,S. pet. 3,250,679 (1965, 1966 to John Wyeth A Brother). 

The acetoxymethyl ester of benzylpenicillin is penamecillin (Havapen, 1). It is an almost white, free-flowing powder lacking the characteristic odour and taste which make penicillins generally unpalatable when administered in tablet or... 

After oral administration to the dog, penamecillin (VII), which is the acetoxymethyl ester of benzylpencillin, produces prolonged benzylpencillin serum levels.According to pharmacokinetic evidence O, the penamecillin is slowly absorbed unchanged throughout the intestinal tract and then is rapidly hydrolyzed to benzylpenicillin by nonspecific esterases. Compound VIII is an example of the hitherto unknown penicillin aldehydes for which a general synthesis was developed. 

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