Bacampicillin

Bacampicillin

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral
ATC code	J01CA06 (WHO)
Pharmacokinetic data
Metabolism	Rapidly hydrolyzed to ampicillin
Identifiers
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
CAS Number	37661-08-8
PubChem (CID)	39849
DrugBank	DB01602
ChemSpider	390135
UNII	8GM2J22278
ChEBI	CHEBI:2968
ChEMBL	CHEMBL1583
Chemical and physical data
Formula	C21H27N3O7S
Molar mass	465.519 g/mol
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 Key:PFOLLRNADZZWEX-FFGRCDKISA-N
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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

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.

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

• Sarpicillin

References

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).