Hetacillin
Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. It is a prodrug and has no antibacterial activity itself,[1] but quickly splits off acetone in the human body to form ampicillin,[2] which is active against a variety of bacteria.
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| Trade names | Hetacin, Versapen |
| AHFS/Drugs.com | Veterinary Use |
| Routes of administration | Intramammary injection |
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| ECHA InfoCard | 100.020.466 |
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| Formula | C19H23N3O4S |
| Molar mass | 389.47 g·mol−1 |
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Administration
Hetacillin can be administered orally. The potassium salt, hetacillin potassium, is administered by injection, either intravenously[3] or intramuscularly.[4] It is sold under the trade name Hetacin for intramammary injection in veterinary use.[5]
Hetacillin was withdrawn from the market for human use when the discovery was made that it had no advantages over ampicillin.[6]
Chemistry
Hetacillin is prepared from ampicillin and acetone. In aqueous solutions it is unstable, with a half life of 15 to 30 minutes at 37 °C (99 °F) and pH 7, quickly releasing acetone again.[7]
As opposed to ampicillin, hetacillin is only marginally broken down by the bacterial enzyme beta-lactamase, at least in vitro.
References
- "Hetacillin". Drugbank.
- Sutherland R, Robinson OP (June 1967). "Laboratory and pharmacological studies in man with hetacillin and ampicillin". British Medical Journal. 2 (5555): 804–8. doi:10.1136/bmj.2.5555.804. PMC 1843140. PMID 5182358.
- Tsuji Y, Tomita M (August 1970). "[Clinical effect of intravenous injection of potassium hetacillin (Versapen 'Bristol') on pre- and post-operative infections] (in Japanese)". The Japanese Journal of Antibiotics. 23 (4): 400–2. PMID 5312791.
- Hara M, Takemoto S, Kawazu T (December 1970). "[Therapeutic experience with intramuscular injection of hetacillin (Versapen 'Bristol') in infection in children] (in Japanese)". The Japanese Journal of Antibiotics. 23 (5): 482–6. PMID 5314634.
- Hetacin-K Intramammary Infusion for Veterinary Use
- Smith JT, Hamilton-Miller J (1970). "Hetacillin: A Chemical and Biological Comparison with Ampicillin". Chemotherapy. 15 (6): 366–78. doi:10.1159/000220703. PMID 5514976.
- Faine S, Harper M (January 1973). "Independent antibiotic actions of hetacillin and ampicillin revealed by fast methods". Antimicrobial Agents and Chemotherapy. 3 (1): 15–8. doi:10.1128/aac.3.1.15. PMC 444353. PMID 4597707.