Hetacillin: Difference between revisions

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imported>Caesar Schinas
m (Robot: Automated text replacement (-* {{CZMed +{{CZMed))
imported>David E. Volk
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{{Chem infobox
|align=right
|image=[[Image:Hetacilliln structure.jpg|center|thumb|250px|{{#ifexist:Template:Hetacilliln structure.jpg/credit|{{Hetacilliln structure.jpg/credit}}<br/>|}}]]
|width=250px
|molname=hetacillin
|synonyms= 
|molformula= C<sub>19</sub>H<sub>23</sub>N<sub>3</sub>O<sub>4</sub>S
|molmass= 389.4686
|uses=antibiotic drug
|properties=beta-lactam
|hazards=see drug interactions
|iupac= see chemistry section
|casnumber=3511-16-8
}}
'''Hetacillin''' is a [[penicillin]]-like, beta-[[lactam]]-based [[antibiotic]] prodrug used to treat infections, usually from [[Gram-positive]] bacteria.  It is sold under the brand names Hetacillin potassium®, Versapen® and Versapen-k®.
== Mechanism of action ==
Hetacillin is a prodrug with no antibacterial activity, but it is metabolized into the antibiotic [[ampicillin]].  Hetacillin is prepared by reacting ampicillin with acetone because ampicillin is much less stable towards ring-opening reactions. Once converted to ampicillin, the ampicillin interferes with the final stage of cell wall synthesis by binding to penicillin-binding proteins, leading to [[autolysis]] of the bacteria by [[autolysin]] enzymes.
== Chemistry ==
It is a beta-[[lactam]] structure, and its chemical name is (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.  Its chemical formula is C<sub>19</sub>H<sub>23</sub>N<sub>3</sub>O<sub>4</sub>S (MW = 389.4686 g/mol).  Hetacillin is susceptible to degradation in bacteria that produce [[beta-lactamase]].
== External links ==
== External links ==
{{CZMed}}
{{CZMed}}

Revision as of 10:23, 20 June 2009

External links

The most up-to-date information about Hetacillin and other drugs can be found at the following sites.

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