Bacampicillin

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Bacampicillin
Bacampicillin.png
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration
Oral
ATC code
Pharmacokinetic data
MetabolismRapidly hydrolyzed to ampicillin
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H27N3O7S
Molar mass465.519 g/mol g·mol−1
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Bacampicillin (INN) is a penicillin antibiotic. It is a prodrug of ampicillin with improved oral bioavailability.[1]

It is sold under the brand names Spectrobid (Pfizer) and Penglobe (AstraZeneca).

Synthesis[edit]

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:[2][3]

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.

See also[edit]

References[edit]

  1. ^ Bodin NO; Ekström B; Forsgren U; et al. (November 1975). "Bacampicillin: a New Orally Well-Absorbed Derivative of Ampicillin". Antimicrob Agents Chemother. 8 (5): 518–25. PMC 429411. PMID 1211909.
  2. ^ B. A. Ekstrom, O. K. J. Kovacs, and B. O. H. Sjoberg, DE 2311328  (1973). Chem. Abstr., 80, 14921q(1974).
  3. ^ B. A. Ekstrom, B. O. H. Sjoberg, DE 2144457 ; eidem, U.S. Patent 3,873,521 and U.S. Patent 3,939,270 (1972, 1975 and 1976 all to Astra).