Hetacillin

Hetacillin
Clinical data
Trade names	Hetacin, Versapen
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	443387;
DrugBank	DB00739 ;
ChemSpider	391616 ;
UNII	TN4JSC48CV;
KEGG	D01074 ;
ChEMBL	ChEMBL1201116 ;
CompTox Dashboard (EPA)	DTXSID4023121 ;
ECHA InfoCard	100.020.466
Chemical and physical data
Formula	C19H23N3O4S
Molar mass	389.47 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N3C(=O)[C@H](NC3(C)C)c4ccccc4)C(=O)O)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-NFFDBFGFSA-N ;
	(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,^[1] but quickly splits off acetone in the human body to form ampicillin,^[2] 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^[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Hetacillin was withdrawn from the market for human use when the discovery was made that it had no advantages over ampicillin.^[6]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]

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.

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

[DrugBank-1] "Hetacillin". Drugbank.

[Sutherland-2] 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.

[3] 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.

[4] 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.

[5] Hetacin-K Intramammary Infusion for Veterinary Use

[6] 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-7] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]