関: hetacillin potassium

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/11/22 00:01:34」(JST)

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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 antibacterial-related article is a stub. You can help Wikipedia by expanding it.

English Journal

Short communication: Pharmacokinetics of intramammary hetacillin in dairy cattle milked 3 times per day.

Lindquist DA1, Baynes RE1, Smith GW2.
Journal of dairy science.J Dairy Sci.2015 Mar;98(3):1856-61. doi: 10.3168/jds.2014-8715. Epub 2014 Dec 26.
Mastitis remains a critical disease in the dairy industry and the use of intramammary antibiotics plays a critical role in mastitis treatment. Hetacillin is currently approved as an intramammary antibiotic that is used to treat mastitis in dairy cows. It is approved for once a day administration and
PMID 25547305

Treatments of clinical mastitis occurring in cows on 51 large dairy herds in Wisconsin.

Oliveira L1, Ruegg PL2.
Journal of dairy science.J Dairy Sci.2014 Sep;97(9):5426-36. doi: 10.3168/jds.2013-7756. Epub 2014 Jul 3.
Antimicrobials are frequently used for treatment of bovine mastitis and few studies have examined modern treatment strategies on large US dairy farms. The objective of this study was to describe treatment practices for clinical mastitis occurring in cows on large dairy herds in Wisconsin. Treatments
PMID 24997660

Comparison of seven antibiotic treatments with no treatment for bacteriological efficacy against bovine mastitis pathogens.

Wilson DJ1, Gonzalez RN, Case KL, Garrison LL, Gröhn YT.
Journal of dairy science.J Dairy Sci.1999 Aug;82(8):1664-70.
Milk culture results were retrospectively reviewed from 9007 cases of subclinical mastitis affecting cows housed in dairy herds located in New York and northern Pennsylvania. Cases included in this analysis had at least one mastitis pathogen isolated from the initial milk sample, were recultured wit
PMID 10480091

Japanese Journal

Determination of β-Lactam Antibiotics in Water by Fluorescence Quenching of Mercurochrome, and Application for Simple Investigation of Potency

森逸男,藤田芳一,生田絹子,北野尚子,川辺博司,中橋義弘,加藤圭司,稲森善彦
Chemical & pharmaceutical bulletin 37(7), 1827-1830, 1989-07-25
… The calibration graphs were linear over the ranges of about 0-6 μg/ml β-lactam antibiotics penicillins (AB-PC, penicillin G, sulbenicillin, amoxicillin, cyclacillin, oxacillin, hetacillin and piperacillin) and cepham antibiotics (CEX, cefazolin, cephaloglycin, cephaloridine and cefpyramide), and the relative standard deviation was 2.7% for 1.4 μg/ml of AB-PC(n=5).This fluorescence quenching reaction between mercurochrome and β-lactam antibiotics was applied in a survey of decomposition and remaining potency of β-lactam antibiotics. …
NAID 110003627868

Synthesis and Oral Absorption of Hetacillin and Hetamoxicillin Labile Esters(Medicinal Chemistry,Chemical)

GUBERT SANTIAGO,PALACIN CELIA,SACRISTAN AURELIO,ORTIZ JOSE A.
Chemical & pharmaceutical bulletin 35(6), 2366-2372, 1987-06-25
… Nine esters of hetacillin or hetamoxicillin were synthesized as ampicillin and amoxicillin derivatives with the aim of obtaining improved plasma levels after oral administration. … Out of these esters, which are devoid of apparent toxic effects, the benzyloxymethyl ester of hetacillin(FI-5204) gave the best result and was chosen for subsequent studies. …
NAID 80003459844

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リンク元	「ヘタシリン」
拡張検索	「hetacillin potassium」

「ヘタシリン」

Hetacillin
Systematic (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
Clinical data
Trade names	Hetacin
AHFS/Drugs.com	Veterinary Use
Legal status	US: ℞-only;
Routes of; administration	Intramammary injection
Identifiers
CAS Number	3511-16-8
ATC code	J01CA18
PubChem	CID: 193260
DrugBank	DB00739
ChemSpider	167708
UNII	TN4JSC48CV
KEGG	D01074
ChEMBL	CHEMBL1201116
Chemical data
Formula	C19H23N3O4S
Molecular mass	389.469 g/mol
	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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