Pivampicillin

drugbox
IUPAC_name = 2,2-dimethylpropanoyloxymethyl (2"S",5"R",6"R")-
6-{ [(2"R")-2-amino-2-phenyl-acetyl] amino}-3,3-
dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0]
heptane-2-carboxylate

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CAS_number = 33817-20-8
ATC_prefix = J01
ATC_suffix = CA02
PubChem = 33478
DrugBank =
C = 22 | H = 29 | N = 3 | O = 6 | S = 1
molecular_weight = 463.548 g/mol
bioavailability =
protein_bound =
metabolism =
elimination_half-life =
excretion = Renal (76%)
pregnancy_AU =
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legal_UK =
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routes_of_administration = Oral

Pivampicillin is a pivaloyloxymethylester 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. [cite journal |author=Holme E, Greter J, Jacobson CE, "et al" |title=Carnitine deficiency induced by pivampicillin and pivmecillinam therapy |journal=Lancet |volume=2 |issue=8661 |pages=469–73 |year=1989 |month=August |pmid=2570185 |doi= |url=http://linkinghub.elsevier.com/retrieve/pii/S0140-6736(89)92086-2] cite journal |author=Brass EP |title=Pivalate-generating prodrugs and carnitine homeostasis in man |journal=Pharmacol Rev |volume=54 |issue=4 |pages=589–98 |year=2002 |month=December |pmid=12429869 |doi= |url=http://pharmrev.aspetjournals.org/cgi/pmidlookup?view=long&pmid=12429869] 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, [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 |year=1995 |month=June |pmid=7551831 |doi= |url=http://linkinghub.elsevier.com/retrieve/pii/S1077315085710368] it is unlikely to be of clinical significance; long-term use, however, appears problematic and is not recommended. [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 |year=1992 |month=September |pmid=1514015 |doi= |url=] [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 |year=2007 |month=September |pmid=17724113 |doi=10.1542/peds.2007-0339]

References