63699-71-8

Upstream product

• 37660-97-2 (1'S)-1'-ethoxycarbonyloxyethyl 6β-phenylacetamidopenicillanate 
• 90962-82-6 (1'S)-1'-ethoxycarbonyloxyethyl 6β-(1-chloro-2-phenylethylimino)penicillanate 
• 58570-32-4 hexahydro-1H-azepin-1-yl-chloroformiminium chloride 
• 90989-29-0 (1'S)-1'-ethoxycarbonyloxyethyl 6β-aminopenicillanate hydrochloride 

Relevant academic research and scientific papers

Bacmecillinam, a new ester pro-drug of mecillinam: Synthesis and biological evaluation

Bacmecillinam is a new orally well-absorbed pro-drug of the amidinopenicillin mecillinam, of which it is the I'-ethoxycarbonyloxyethyl ester. Synthesis from the corresponding ester of benzympenicillin is described and reaction intermediates have been isolated and characterised. Bacmecillinam shows good stability at pH 1.2 and 7.4 though is is more rapidly hydrolysed than pivmecillinam by human serum. Extremely low levels (in the ng/g range) of unhydrolysed ester were detectable HPLC in peripheral blood of dogs and humans following oral administration. Absorption of the pro-drug from the gastrointestinal tract of dogs and mice was rapid giving mecillinam levels comparable to those following pivmecillinam. A study in rats showed bacmecillinam to have good tissue penetration properties. Bacmecillinam had a protective effect superior to bacampicillin in mice experimentally infected with an E. coli strain.