bacampicillin bacampicillin bacampicillin (inn) is a penicillin antibiotic. it is a prodrug of ampicillin with improved oral bioavailability. bacampicillinclinical dataahfs/drugs.commicromedex detailed consumer informationroutes ofadministrationoraldrug classaminopenicillinatc codej01ca06 (who) pharmacokinetic datametabolismrapidly hydrolyzed to ampicillinidentifiers iupac name 1-ethoxycarbonyloxyethyl (2s,5r)-6-amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylate cas number50972-17-3 nhcl: 37661-08-8 ypubchem cid39849drugbankdb01602 ychemspider390135 yunii8gm2j22278hcl: pm034u953t ychebichebi:2968 ychemblchembl1583 ycomptox dashboard (epa)dtxsid2048030 chemical and physical dataformulac21h27n3o7smolar mass465.52 g·mol−1 inchi inchi=1s/c21h27n3o7s/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18h,5,22h2,1-4h3,(h,23,25)/t11?,13-,14-,15+,18-/m1/s1 ykey:pfollrnadzzwex-ffgrcdkisa-n y ny (what is this?) (verify) it was sold under the brand names spectrobid (pfizer) and penglobe (astrazeneca).in 2015, pfizer discontinued spectrobid, and no generic manufacturer has taken over production. bacampicillin is thus unavailable in the united states, and is no longer fda approved. synthesis semi-synthetic antibiotic related to penicillin. the relatively small chemical difference between ampicillin and benzylpenicillin not only allows for substantial oral activity but also results in a substantial broadening of antimicrobial spectrum so as to allow for use against many gram-negative bacteria. many devices have been employed in order to enhance still further the oral absorption of ampicillin. bacampicillin is a prodrug of ampicillin designed for this purpose. bacampicillin synthesis: an azidopenicillin sodium salt (1) is reacted with mixed carbonate ester 2 (itself prepared from acetaldehyde and ethyl chloroformate) to give ester 3. reduction of the azido linkage with hydrogen and a suitable catalyst produces bacampillin (4). both enantiomers are active. the drug is rapidly absorbed from the gastrointestinal tract and is quickly cleaved by serum esterases to bioactive ampicillin, acetaldehyde, co2 and ethanol.