|ATC code||J01CA18 (WHO)|
IUPAC name: (2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
|Chemical and physical data|
|Molar mass||389.469 g/mol|
|3D model (Jmol)||Interactive image|
|(what is this?)|
Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. It is a prodrug and it has no antibacterial activity itself, but quickly splits of acetone in the human body to form ampicillin, which is active against a variety of bacteria.
Hetacillin can be administered orally. The potassium salt, hetacillin potassium, is administered by injection, either intravenously or intramuscularly. It is sold under the trade name Hetacin for intramammary injection in veterinary use.
Hetacillin was removed from the market for human use when the discovery was made that it is actually cleaved in the gastrointestinal tract to formaldehyde and had no advantages over ampicillin.
- Drugbank: Hetacillin
- Sutherland, R.; Robinson, O. P. (1967). "Laboratory and pharmacological studies in man with hetacillin and ampicillin". British Medical Journal. 2 (5555): 804–808. doi:10.1136/bmj.2.5555.804. PMC . PMID 5182358.
- Hetacin-K Intramammary Infusion for Veterinary Use
- Faine, S.; Harper, M. (1973). "Independent antibiotic actions of hetacillin and ampicillin revealed by fast methods". Antimicrobial Agents and Chemotherapy. 3 (1): 15–18. doi:10.1128/aac.3.1.15. PMC . PMID 4597707.
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