Lillacillin,Takeda,Japan,1973
ChEBI: A penicillin antibiotic having a 6beta-[phenyl(sulfo)acetamido] side-chain.
To a suspension of 1.08 parts by weight of 6-aminopenicillanic acid in 8 parts
by volume of water is added 1.48 parts by weight of sodium bicarbonate.
After the mixture is dissolved, a solution of 1.18 parts by weight of α-sulfophenylacetyl chloride in 10 parts by volume of diethylether is gradually
added thereto. The mixture is stirred at a temperature in the neighborhood of
0°C for 1 hour. The aqueous layer is washed twice with 10 parts by volume of
portions of ether and adjusted to pH 1.2 with cation exchange resin of
polystyrene sulfonic acid type under constant cooling. Then the solution is
washed twice with 15 parts by volume of portions of ethyl acetate, followed
by extraction twice with 15 parts by volume of portions of n-butanol. The
extracts are combined and washed twice with 15 parts by volume of portions
of water and, then, extracted with an aqueous solution of sodium bicarbonate.
The extract is adjusted to pH 6.5, washed with ether and lyophilized to give
the sodium salt of α-sulfobenzylpenicillin. Yield is 1.2 parts by weight.
α-Sulfobenzylpenicillin, a semisynthetic penicillin supplied
as the disodium salt. Its antimicrobial spectrum and pharmacokinetic pharmacokinetic
behavior closely resemble those of carbenicillin.
Following intravenous administration of 4 g, the mean plasma
concentration at 1 h was approximately 160 mg/L, with a
plasma elimination half-life of around 70 min. It is largely
excreted in the urine, about 80% of the dose appearing in the
first 24 h, less than 5% as the penicilloic acid. It has been
noted that the penicilloic acid causes much stronger platelet
aggregation than its parent. It is of very limited availability.
