Pivampicillin
Saunders Veterinary Dictionary:
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pivampicillin
An ester of ampicillin with the same broad spectrum of antibiotic activity.
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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.
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
- ^ 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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Saunders Veterinary Dictionary
Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.
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