7-(2,2-Dimethyl-5-oxo-4-phenyl-imidazolidin-1-yl)-3,3-dimethyl-6-oxo-2-thia-5-azabicyclo[3.2.0]heptane-4-carboxylic acid

Description

Hetacillin was synthesized by Bristol-Myers Laboratories in 1964. It shows activity as strong as that of ampicillin against a variety of gram-positive and gram-negative bacteria. Hetacillin shows almost the same pharmacokinetic properties as ampicillin when administered orally and a later serum peak when given by intramuscular administration. When administered either orally or intramuscularly, it is hydrolyzed in vivo into ampicillin. Therefore, the clinical applications of hetacillin are the same as those of ampicillin.

Originator

Natacillin,Bristol Banyu,Japan,1970

Uses

Antibacterial.

Uses

Hetacillin is a β-lactam antibiotic.

Definition

ChEBI: Hetacillin is a penicillin. It has a role as an antibacterial drug. It is a conjugate acid of a hetacillin(1-).

Manufacturing Process

To 100 grams of α-aminobenzylpenicillin slurried in 2,500 ml of acetone is added 200 ml of a 22% solution of potassium ethylhexanoate in dry n-butanol and the mixture is warmed to 45°C whereupon the acid dissolves. After the mixture is agitated for 1 hour at 40° to 45°C, the product begins to crystallize out. Agitation is continued for 4 hours at 45°C after which the product, the potassium salt of hetacillin, is collected by filtration, washed with 500 ml of dry acetone, dried for 17 hours at 40°C and found to weigh 70.0 grams.

brand name

Versapen-K (Bristol-Myers Squibb) .

Therapeutic Function

Antibacterial