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Prodrug
Hetacillin
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Hetacillin

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Hetacillin
Hetacillin structure.svg
Clinical data
Trade names Hetacin, Versapen
AHFS/Drugs.com Veterinary Use
Routes of
administration		 Intramammary injection
ATC code
Legal status
Legal status
Identifiers
  • (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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.020.466
Chemical and physical data
Formula C19H23N3O4S
Molar mass 389.47 g·mol−1
3D model (JSmol)
  • CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N3C(=O)[C@H](NC3(C)C)c4ccccc4)C(=O)O)C
  • InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1 ☒N
  • Key:DXVUYOAEDJXBPY-NFFDBFGFSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. It is a prodrug and has no antibacterial activity itself, but quickly splits off acetone in the human body to form ampicillin, which is active against a variety of bacteria.

Administration

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Hetacillin was withdrawn from the market for human use when the discovery was made that it had no advantages over ampicillin.

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.

As opposed to ampicillin, hetacillin is only marginally broken down by the bacterial enzyme beta-lactamase, at least in vitro.


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