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Pivampicillin
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Oral
ATC code
Pharmacokinetic data
ExcretionRenal (76%)
Identifiers
  • 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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.046.975 Edit this at Wikidata
Chemical and physical data
FormulaC22H29N3O6S
Molar mass463.55 g·mol−1
3D model (JSmol)
  • O=C(OCOC(=O)C(C)(C)C)[C@@H]2N3C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)N)[C@H]3SC2(C)C
  • InChI=1S/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13-,14-,15+,18-/m1/s1 checkY
  • Key:ZEMIJUDPLILVNQ-ZXFNITATSA-N checkY
 ☒NcheckY (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[edit]

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[edit]

Worldwide, pivampicillin is only available in Denmark, where it is sold as Pondocillin® by PharmaCoDane, or Miraxid® by LEO Pharma.[6]

References[edit]

  1. ^ Holme E, Greter J, Jacobson CE, Lindstedt S, Nordin I, Kristiansson B, Jodal U (August 1989). "Carnitine deficiency induced by pivampicillin and pivmecillinam therapy". Lancet. 2 (8661): 469–473. doi:10.1016/S0140-6736(89)92086-2. PMID 2570185. S2CID 31555161.
  2. ^ a b c Brass EP (December 2002). "Pivalate-generating prodrugs and carnitine homeostasis in man". Pharmacological Reviews. 54 (4): 589–598. doi:10.1124/pr.54.4.589. PMID 12429869. S2CID 14507215.
  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". Biochemical and Molecular Medicine. 55 (1): 77–79. doi:10.1006/bmme.1995.1036. PMID 7551831.
  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". Scandinavian Journal of Clinical and Laboratory Investigation. 52 (5): 361–372. 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–e741. doi:10.1542/peds.2007-0339. PMID 17724113. S2CID 40136171.
  6. ^ "Pondocillin®". Retrieved 2016-09-18.
source: https://en.wikipedia.org/wiki/Pivampicillin

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