BACAMPICILLIN HYDROCHLORIDE

Description

Bacampicillin was synthesized by Ekstrom¨ et al. of Astra Lakemedel in 1975. It is ¨ more stable against acid than ampicillin and more rapidly absorbed orally; its absorption is less affected by a patient’s most recent meal than is the case for ampicillin. Bacampicillin is hydrolyzed by intestinal esterase after oral administration and then behaves the same as ampicillin. In double-blind comparison studies, bacampicillin was shown to be as effective as ampicillin when administered at half the dose.

Chemical properties

White or almost white powder or granules, hygroscopic.

Originator

Penglobe,Astra,W. Germany,1977

The Uses of BACAMPICILLIN HYDROCHLORIDE

Bacampicillin is a penicillin class of antibiotic. Bacampicillin is a prodrug of ampicillin (A634300) with improved oral bioavailability.

Definition

ChEBI: The hydrochloride salt of bacampicillin.

Manufacturing Process

1'-Ethoxycarbonyloxyethyl 6-(D-α-azidophenylacetamido)penicillinate (98 g) was prepared from sodium 6-(D-α-azidophenylacetamido)penicillinate (397 g, 1 mol), α-chlorodiethylcarbonate (458 g, 3 mols) and sodium bicarbonate (504 g, 6 mols). The product showed strong IR absorption at 2090 cm-1 and 1780-1750 cm-1 showing the presence of azido group and β-lactam and ester carbonyls.
It was dissolved in ethyl acetate (700 ml) and hydrogenated at ambient conditions over a palladium (5%)on carbon catalyst (18 g). The catalyst was removed by filtration and washed with ethyl acetate. The combined filtrates were extracted with water at pH 2.5 by addition of dilute hydrochloric acid. Lyophilization of the aqueous phase gave the hydrochloride of 1'- ethoxycarbonyloxyethyl 6-(D-α-aminophenylacetarnido)penicillinate (94 g), MP 171°-176°C.

brand name

Spectrobid (Pfizer).

Therapeutic Function

Antibacterial

Clinical Use

Bacampicillin hydrochloride (Spectrobid) is the hydrochloridesalt of the 1-ethoxycarbonyloxyethyl ester of ampicillin.It is a prodrug of ampicillin with no antibacterial activity.After oral absorption, bacampicillin is hydrolyzed rapidly byesterases in the plasma to form ampicillin.
Oral absorption of bacampicillin is more rapid and completethan that of ampicillin and less affected by food.Plasma levels of ampicillin from oral bacampicillin exceedthose of oral ampicillin or amoxicillin for the first 2.5 hoursbut thereafter are the same as for ampicillin and amoxicillin.49 Effective plasma levels are sustained for 12 hours,allowing twice-a-day dosing.

Safety Profile

Poison by intraperitoneal andintravenous routes. Mildly toxic by ingestion andsubcutaneous routes. When heated to decomposition itemits very toxic fumes of NOx, SOx, and HCl.