Pivampicillin

Chemical compound From Wikipedia, the free encyclopedia

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.

AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administrationOral
ATC code
ExcretionRenal (76%)
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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
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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
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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

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