Chemistry:Pivampicillin
 | |
| Clinical data | |
|---|---|
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| Routes of administration | Oral |
| ATC code | |
| Pharmacokinetic data | |
| Excretion | Renal (76%) |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| Chemical and physical data | |
| Formula | C22H29N3O6S |
| Molar mass | 463.55 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (what is this?) (verify) | |
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 effect 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, is not recommended.[2][4][5]
Availability
Worldwide, pivampicillin is only available in Denmark, where it is sold as Pondocillin® by PharmaCoDane, or Miraxid® by LEO Pharma.[6]
References
- ↑ "Carnitine deficiency induced by pivampicillin and pivmecillinam therapy". Lancet 2 (8661): 469–473. August 1989. doi:10.1016/S0140-6736(89)92086-2. PMID 2570185.
- ↑ 2.0 2.1 2.2 "Pivalate-generating prodrugs and carnitine homeostasis in man". Pharmacological Reviews 54 (4): 589–598. December 2002. doi:10.1124/pr.54.4.589. PMID 12429869.
- ↑ "Effect of short-term treatment with pivalic acid containing antibiotics on serum carnitine concentration--a risk irrespective of age". Biochemical and Molecular Medicine 55 (1): 77–79. June 1995. doi:10.1006/bmme.1995.1036. PMID 7551831.
- ↑ "Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children". Scandinavian Journal of Clinical and Laboratory Investigation 52 (5): 361–372. September 1992. doi:10.3109/00365519209088371. PMID 1514015.
- ↑ "Carnitine-associated encephalopathy caused by long-term treatment with an antibiotic containing pivalic acid". Pediatrics 120 (3): e739–e741. September 2007. doi:10.1542/peds.2007-0339. PMID 17724113.
- ↑ "Pondocillin®". https://pro.medicin.dk/Medicin/Praeparater/524.
 |  |
