Hetacillin

Hetacillin
Clinical data
Trade names	Hetacin
AHFS/Drugs.com	Veterinary Use
Routes of; administration	Intramammary injection
ATC code	J01CA18 (WHO) ;
Legal status
Legal status	US: ℞-only;
Identifiers
	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;
CAS Number	3511-16-8 ;
PubChem CID	193260;
DrugBank	DB00739 ;
ChemSpider	167708 ;
UNII	TN4JSC48CV;
KEGG	D01074 ;
ChEMBL	ChEMBL1201116 ;
CompTox Dashboard (EPA)	DTXSID4023121 ;
ECHA InfoCard	100.020.466
Chemical and physical data
Formula	C19H23N3O4S
Molar mass	389.469 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](N2C(=O)C(c1ccccc1)NC2(C)C)[C@H]4SC3(C)C;
	InChI 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 ; Key:DXVUYOAEDJXBPY-XQERAMJGSA-N ;
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Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. It is a prodrug and it has no antibacterial activity itself,^[1] but quickly splits of acetone in the human body to form ampicillin,^[2] which is active against a variety of bacteria.

Administration

Hetacillin can be administered orally.^[2] The potassium salt, hetacillin potassium, is administered by injection, either intravenously or intramuscularly.^{[citation needed]} It is sold under the trade name Hetacin for intramammary injection in veterinary use.^[3]

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.^{[citation needed]}

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.^[1]^[4]

As opposed to ampicillin, hetacillin is only marginally broken down by the bacterial enzyme beta-lactamase, at least in vitro.^[4]

References

^ ^a ^b Drugbank: Hetacillin
^ ^a ^b 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 1843140. PMID 5182358.
^ Hetacin-K Intramammary Infusion for Veterinary Use
^ ^a ^b 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 444353. PMID 4597707.

This systemic antibiotic-related article is a stub. You can help Wikipedia by expanding it.

[DrugBank-1] Drugbank: Hetacillin

[Sutherland-2] 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 1843140. PMID 5182358.

[3] Hetacin-K Intramammary Infusion for Veterinary Use

[Faine-4] 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 444353. PMID 4597707.

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