Pivampicillin
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| Systematic (IUPAC) name | |
| 2,2-Dimethylpropanoyloxymethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenyl-acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | |
| Clinical data | |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| Pregnancy cat. | ? |
| Legal status | ? |
| Routes | Oral |
| Pharmacokinetic data | |
| Excretion | Renal (76%) |
| Identifiers | |
| CAS number | 33817-20-8  |
| ATC code | J01CA02 |
| PubChem | CID 33478 |
| DrugBank | DB01604 |
| ChemSpider | 30899 |
| UNII | 0HLM346LL7 |
| KEGG | D08396 |
| ChEBI | CHEBI:8255 |
| ChEMBL | CHEMBL323354  |
| Chemical data | |
| Formula | C22H29N3O6S |
| Mol. mass | 463.548 g/mol |
| SMILES | eMolecules & PubChem |
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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.
[edit] 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]
[edit] References
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
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