Bacampicillin

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Bacampicillin
Bacampicillin.png
Systematic (IUPAC) name
1-Ethoxycarbonyloxyethyl (2S,5R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Routes of
administration
Oral
Pharmacokinetic data
Metabolism Rapidly hydrolyzed to ampicillin
Identifiers
CAS Registry Number 37661-08-8 N
ATC code J01CA06
PubChem CID: 39849
DrugBank DB01602 YesY
ChemSpider 390135 YesY
UNII 8GM2J22278 YesY
ChEBI CHEBI:2968 YesY
ChEMBL CHEMBL1583 YesY
Chemical data
Formula C21H27N3O7S
Molecular mass 465.519 g/mol
 N (what is this?)  (verify)

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 witrh 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).