Pivampicillin: Difference between revisions

Latest revision as of 10:58, 15 February 2025

Pivampicillin[edit]

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.

Mechanism of Action[edit]

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.

Pharmacokinetics[edit]

Pivampicillin is absorbed from the gastrointestinal tract and is rapidly converted to ampicillin in the body. The conversion occurs primarily in the liver, where the pivaloyl group is cleaved off, releasing the active ampicillin. The bioavailability of ampicillin from pivampicillin is higher compared to oral ampicillin, making it a more effective option for oral administration.

Clinical Uses[edit]

Pivampicillin is used to treat a variety of infections caused by susceptible bacteria, including:

Side Effects[edit]

Common side effects of pivampicillin include:

Gastrointestinal disturbances such as nausea, vomiting, and diarrhea
Allergic reactions such as rash, itching, and anaphylaxis
Hepatotoxicity due to the release of pivalic acid

Precautions[edit]

Patients with a history of penicillin allergy should avoid using pivampicillin due to the risk of cross-reactivity. It is also important to monitor liver function in patients receiving long-term therapy, as the release of pivalic acid can lead to liver damage.

Related Pages[edit]

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+== Pivampicillin ==
-'''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.
-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==
+== 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]]
+Pivampicillin is absorbed from the gastrointestinal tract and is rapidly converted to ampicillin in the body. The conversion occurs primarily in the liver, where the pivaloyl group is cleaved off, releasing the active ampicillin. The bioavailability of ampicillin from pivampicillin is higher compared to oral ampicillin, making it a more effective option for oral administration.
+== Clinical Uses ==
+Pivampicillin is used to treat a variety of infections caused by susceptible bacteria, including:
+* [[Respiratory tract infections]]
+* [[Urinary tract infections]]
+* [[Skin and soft tissue infections]]
+* [[Gastrointestinal infections]]
+== Side Effects ==
+Common side effects of pivampicillin include:
+* [[Gastrointestinal disturbances]] such as nausea, vomiting, and diarrhea
+* [[Allergic reactions]] such as rash, itching, and anaphylaxis
+* [[Hepatotoxicity]] due to the release of pivalic acid
+== Precautions ==
+Patients with a history of [[penicillin allergy]] should avoid using pivampicillin due to the risk of cross-reactivity. It is also important to monitor liver function in patients receiving long-term therapy, as the release of pivalic acid can lead to liver damage.
+== Related Pages ==
+* [[Ampicillin]]
+* [[Beta-lactam antibiotics]]
+* [[Antibiotic resistance]]
+[[Category:Antibiotics]]