Bacampicillin

Bacampicillin (INN) is a penicillin antibiotic. It is a prodrug of ampicillin with improved oral bioavailability.^[1]

Bacampicillin

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral
Drug class	aminopenicillin
ATC code	J01CA06 (WHO)
Pharmacokinetic data
Metabolism	Rapidly hydrolyzed to ampicillin
Identifiers
IUPAC name 1-Ethoxycarbonyloxyethyl (2S,5R)-6-{{#parsoidfragment:1}}(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
CAS Number	50972-17-3 N HCL: 37661-08-8 Y
PubChem CID	39849
DrugBank	DB01602 Y
ChemSpider	390135 Y
UNII	8GM2J22278 HCL: PM034U953T Y
ChEBI	CHEBI:2968 Y
ChEMBL	ChEMBL1583 Y
CompTox Dashboard (EPA)	DTXSID2048030
Chemical and physical data
Formula	C21H27N3O7S
Molar mass	465.52 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 Y Key: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.^[2] Bacampicillin is thus unavailable in the United States, and is no longer FDA approved.^[3]

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:^[4][5][6][7]

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.^{[citation needed]}