The Full Wiki

More info on Pivampicillin

Pivampicillin: Wikis

Advertisements

Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.

Encyclopedia

From Wikipedia, the free encyclopedia

Pivampicillin
Systematic (IUPAC) name
2,2-dimethylpropanoyloxymethyl (2S,5 R,6R)-
6-{[(2R)-2-amino-2-phenyl-acetyl]amino}-3,3-
dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]
heptane-2-carboxylate
Identifiers
CAS number 33817-20-8
ATC code J01CA02
PubChem 33478
Chemical data
Formula C 22H29N3O6S 
Mol. mass 463.548 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion Renal (76%)
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes 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.[1][2] 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,[3] it is unlikely to be of clinical significance;[2] long-term use, however, appears problematic and is not recommended.[2][4][5]

References

  1. ^ Holme E, Greter J, Jacobson CE, et al. (August 1989). "Carnitine deficiency induced by pivampicillin and pivmecillinam therapy". Lancet 2 (8661): 469–73. doi:10.1016/S0140-6736(89)92086-2. PMID 2570185. http://linkinghub.elsevier.com/retrieve/pii/S0140-6736(89)92086-2.  
  2. ^ a b c Brass EP (December 2002). "Pivalate-generating prodrugs and carnitine homeostasis in man". Pharmacol Rev 54 (4): 589–98. doi:10.1124/pr.54.4.589. PMID 12429869. http://pharmrev.aspetjournals.org/cgi/pmidlookup?view=long&pmid=12429869.  
  3. ^ Abrahamsson K, Holme E, Jodal U, Lindstedt S, Nordin I (June 1995). "Effect of short-term treatment with pivalic acid containing antibiotics on serum carnitine concentration—a risk irrespective of age". Biochem. Mol. Med. 55 (1): 77–9. doi:10.1006/bmme.1995.1036. PMID 7551831. http://linkinghub.elsevier.com/retrieve/pii/S1077315085710368.  
  4. ^ Holme E, Jodal U, Linstedt S, Nordin I (September 1992). "Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children". Scand J Clin Lab Invest 52 (5): 361–72. doi:10.3109/00365519209088371. PMID 1514015.  
  5. ^ Makino Y, Sugiura T, Ito T, Sugiyama N, Koyama N (September 2007). "Carnitine-associated encephalopathy caused by long-term treatment with an antibiotic containing pivalic acid". Pediatrics 120 (3): e739–41. doi:10.1542/peds.2007-0339. PMID 17724113.  
Advertisements

Advertisements






Got something to say? Make a comment.
Your name
Your email address
Message