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.

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>Holme E,

 Carnitine deficiency induced by pivampicillin and pivmecillinam therapy, 
 Lancet, 
 
 Vol. 2(Issue: 8661),
 pp. 469–73,
 DOI: 10.1016/S0140-6736(89)92086-2,
 PMID: 2570185,
 
 
 Full text,</ref><ref name=Brass>Brass EP, 
 Pivalate-generating prodrugs and carnitine homeostasis in man, 
 Pharmacol Rev, 
 
 Vol. 54(Issue: 4),
 pp. 589–98,
 DOI: 10.1124/pr.54.4.589,
 PMID: 12429869,
 
 
 Full text,</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>Abrahamsson K, Holme E, Jodal U, Lindstedt S, Nordin I, 
 Effect of short-term treatment with pivalic acid containing antibiotics on serum carnitine concentration—a risk irrespective of age, 
 Biochem. Mol. Med., 
 
 Vol. 55(Issue: 1),
 pp. 77–9,
 DOI: 10.1006/bmme.1995.1036,
 PMID: 7551831,
 
 
 Full text,</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>Holme E, Jodal U, Linstedt S, Nordin I, 
 Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children, 
 Scand J Clin Lab Invest, 
 
 Vol. 52(Issue: 5),
 pp. 361–72,
 DOI: 10.3109/00365519209088371,
 PMID: 1514015,</ref><ref>Makino Y, Sugiura T, Ito T, Sugiyama N, Koyama N, 
 Carnitine-associated encephalopathy caused by long-term treatment with an antibiotic containing pivalic acid, 
 Pediatrics, 
 
 Vol. 120(Issue: 3),
 pp. e739–41,
 DOI: 10.1542/peds.2007-0339,
 PMID: 17724113,</ref>

References

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Penicillin antibiotics

• penicillins first generation (natural penicillins)
  • benzathine penicillin, procaine penicillin, penicillin g, penicillin v, penicillin vk

• penicillins second generation (penicillinase-resistant penicillins)
  • cloxacillin, dicloxacillin, flucloxacillin, methicillin, nafcillin, oxacillin

• penicillins third generation (aminopenicillins)
  • amoxicillin, ampicillin, ampicillin-sulbactam, bacampicillin, pivampicillin
• see also amoxicillin-clavulanate

• penicillins fourth generation (extended-spectrum penicillins)
  • carbenicillin, mezlocillin, piperacillin, piperacillin-tazobactam, ticarcillin, ticarcillin-clavulanate

• Dailymed label info on Pivampicillin
• FDA Pivampicillin