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| Clinical data | |
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| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| Routes of administration | Oral |
| Drug class | aminopenicillin |
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| Pharmacokinetic data | |
| Metabolism | Rapidlyhydrolyzed toampicillin |
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| Chemical and physical data | |
| Formula | C21H27N3O7S |
| Molar mass | 465.52 g·mol−1 |
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Bacampicillin (INN) is apenicillinantibiotic. It is aprodrug ofampicillin with improved oralbioavailability.[1]
It was sold under the brand namesSpectrobid (Pfizer) andPenglobe (AstraZeneca).In 2015, Pfizer discontinued Spectrobid, and no generic manufacturer has taken over production.[2] Bacampicillin is thus unavailable in the United States, and is no longer FDA approved.[3]
Semi-synthetic antibiotic related to penicillin.
The relatively small chemical difference betweenampicillin andbenzylpenicillin not only allows for substantial oral activity but also results in a substantial broadening of antimicrobial spectrum so as to allow for use against manyGram-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.
An azidopenicillin sodium salt (1) is reacted with mixed carbonate ester2 (itself prepared fromacetaldehyde andethyl chloroformate) to give ester3. 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.[citation needed]
