Hetacillin: Difference between revisions
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'''Hetacillin''' is a [[beta-lactam antibiotic]] that is part of the | '''Hetacillin''' is a [[beta-lactam antibiotic]] that is part of the aminopenicillin family. It is a [[prodrug]] and it has no antibacterial activity itself, but quickly splits of [[acetone]] in the human body to form [[ampicillin]],which is active against a variety of bacteria. | ||
==Administration== | ==Administration== | ||
Hetacillin can be administered orally. | Hetacillin can be administered orally. The [[potassium]] salt, hetacillin potassium, is administered by [[Injection (medicine)|injection]], either intravenously or intramuscularly. It is sold under the trade name '''Hetacin''' for [[Mammary gland|intramammary]] injection in veterinary use. | ||
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. | 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. | ||
==Chemistry== | ==Chemistry== | ||
Hetacillin is prepared from ampicillin and acetone. In aqueous solutions it is unstable, with a half life of 15 to 30 minutes at {{convert|37|°C|°F}} and pH 7, quickly releasing acetone again. | Hetacillin is prepared from ampicillin and acetone. In aqueous solutions it is unstable, with a half life of 15 to 30 minutes at {{convert|37|°C|°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]]''. | As opposed to ampicillin, hetacillin is only marginally broken down by the bacterial enzyme [[beta-lactamase]], at least ''[[in vitro]]''. | ||
==References== | ==References== | ||
{{reflist|2}} | {{reflist|2}} | ||
[[Category:Beta-lactam antibiotics]] | [[Category:Beta-lactam antibiotics]] | ||
[[Category:Prodrugs]] | [[Category:Prodrugs]] | ||
[[Category:Withdrawn drugs]] | [[Category:Withdrawn drugs]] | ||
[[Category: | [[Category:Drug]] |
Latest revision as of 18:34, 8 April 2015
Clinical data | |
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Trade names | Hetacin |
AHFS/Drugs.com | Veterinary Use |
Routes of administration | Intramammary injection |
ATC code | |
Legal status | |
Legal status |
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Identifiers | |
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CAS Number | |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEMBL | |
E number | {{#property:P628}} |
ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value). |
Chemical and physical data | |
Formula | C19H23N3O4S |
Molar mass | 389.469 g/mol |
3D model (JSmol) | |
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(what is this?) (verify) |
WikiDoc Resources for Hetacillin |
Articles |
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Most recent articles on Hetacillin |
Media |
Evidence Based Medicine |
Clinical Trials |
Ongoing Trials on Hetacillin at Clinical Trials.gov Clinical Trials on Hetacillin at Google
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Guidelines / Policies / Govt |
US National Guidelines Clearinghouse on Hetacillin
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Books |
News |
Commentary |
Definitions |
Patient Resources / Community |
Patient resources on Hetacillin Discussion groups on Hetacillin Patient Handouts on Hetacillin Directions to Hospitals Treating Hetacillin Risk calculators and risk factors for Hetacillin
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Healthcare Provider Resources |
Causes & Risk Factors for Hetacillin |
Continuing Medical Education (CME) |
International |
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Business |
Experimental / Informatics |
Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]
Overview
Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. It is a prodrug and it has no antibacterial activity itself, but quickly splits of 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 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.
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 (98.6 °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.
References
- Pages with script errors
- Template:drugs.com link with non-standard subpage
- Articles with changed KEGG identifier
- Articles with changed EBI identifier
- E number from Wikidata
- ECHA InfoCard ID from Wikidata
- Chemical articles with unknown parameter in Infobox drug
- Drugboxes which contain changes to verified fields
- Drugboxes which contain changes to watched fields
- Beta-lactam antibiotics
- Prodrugs
- Withdrawn drugs
- Drug