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-'''Pivampicillin''' is a [[pivaloyloxymethyl]] [[ester]] of [[ampicillin]]. It is a [[prodrug]], which is thought to enhance the oral [[bioavailability]] of ampicillin because of its greater [[lipophilicity]] compared to that of ampicillin.
+[[File:Pivampicillin.svg|thumb|right|Chemical structure of Pivampicillin]]
-==Adverse effects==
+'''Pivampicillin''' is an [[antibiotic]] that belongs to the class of [[beta-lactam antibiotics]]. It is a prodrug of [[ampicillin]], which means it is converted into the active form, ampicillin, in the body. Pivampicillin is used to treat a variety of bacterial infections by inhibiting the synthesis of bacterial cell walls.
-==References==
+== Mechanism of Action ==
-<references />
-{{penicillins}}
+Pivampicillin, like other beta-lactam antibiotics, works by interfering with the synthesis of the [[bacterial cell wall]]. It binds to and inactivates penicillin-binding proteins (PBPs) located inside the bacterial cell wall. This action inhibits the final transpeptidation step of peptidoglycan synthesis, which is crucial for bacterial cell wall integrity. As a result, the bacteria are unable to maintain their cell wall structure, leading to cell lysis and death.
-{{coststubd}}
-[[Category:Beta-lactam antibiotics]]
+== Pharmacokinetics ==
-[[Category:Prodrugs]]

Prab at 13:50, 30 April 2019

2019-04-30T13:50:58Z

New page

'''Pivampicillin''' is a [[pivaloyloxymethyl]] [[ester]] of [[ampicillin]]. It is a [[prodrug]], which is thought to enhance the oral [[bioavailability]] of ampicillin because of its greater [[lipophilicity]] compared to that of ampicillin.

==Adverse effects==
Prodrugs that release [[pivalic acid]] when broken down by the body—such as pivampicillin, [[pivmecillinam]] and [[cefditoren pivoxil]]—have long been known to deplete levels of [[carnitine]].<ref>{{cite journal |author=Holme E |title=Carnitine deficiency induced by pivampicillin and pivmecillinam therapy |journal=Lancet |volume=2 |issue=8661 |pages=469–73 |date=August 1989 |pmid=2570185 |doi= 10.1016/S0140-6736(89)92086-2|url=http://linkinghub.elsevier.com/retrieve/pii/S0140-6736(89)92086-2 |author-separator=, |author2=Greter J |author3=Jacobson CE |display-authors=3 |last4=Greter |first4=Joachim |last5=Lindstedt |first5=Sven |last6=Kristiansson |first6=Bengt |last7=Jodal |first7=Ulf}}</ref><ref name=Brass>{{cite journal |author=Brass EP |title=Pivalate-generating prodrugs and carnitine homeostasis in man |journal=Pharmacol Rev |volume=54 |issue=4 |pages=589–98 |date=December 2002 |pmid=12429869 |doi= 10.1124/pr.54.4.589|url=http://pharmrev.aspetjournals.org/cgi/pmidlookup?view=long&pmid=12429869}}</ref> This is not due to the drug itself, but to pivalate, which is mostly removed from the body by forming a conjugate with carnitine. Although short-term use of these drugs can cause a marked decrease in blood levels of carnitine,<ref>{{cite journal |author=Abrahamsson K, Holme E, Jodal U, Lindstedt S, Nordin I |title=Effect of short-term treatment with pivalic acid containing antibiotics on serum carnitine concentration—a risk irrespective of age |journal=Biochem. Mol. Med. |volume=55 |issue=1 |pages=77–9 |date=June 1995 |pmid=7551831 |doi= 10.1006/bmme.1995.1036|url=http://linkinghub.elsevier.com/retrieve/pii/S1077315085710368}}</ref> it is unlikely to be of clinical significance;<ref name=Brass/> long-term use, however, appears problematic and is not recommended.<ref name=Brass/><ref>{{cite journal |author=Holme E, Jodal U, Linstedt S, Nordin I |title=Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children |journal=Scand J Clin Lab Invest |volume=52 |issue=5 |pages=361–72 |date=September 1992 |pmid=1514015 |doi= 10.3109/00365519209088371|url=}}</ref><ref>{{cite journal |author=Makino Y, Sugiura T, Ito T, Sugiyama N, Koyama N |title=Carnitine-associated encephalopathy caused by long-term treatment with an antibiotic containing pivalic acid |journal=Pediatrics |volume=120 |issue=3 |pages=e739–41 |date=September 2007 |pmid=17724113 |doi=10.1542/peds.2007-0339}}</ref>

==References==
<references />
{{penicillins}}
{{coststubd}}
[[Category:Beta-lactam antibiotics]]
[[Category:Prodrugs]]

Pivampicillin - Revision history

Prab: CSV import

Prab at 13:50, 30 April 2019