Pivampicillin

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.

Pivampicillin

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral
ATC code	J01CA02 (WHO)
Pharmacokinetic data
Excretion	Renal (76%)
Identifiers
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
CAS Number	33817-20-8 Y
PubChem CID	33478
DrugBank	DB01604 Y
ChemSpider	30899 Y
UNII	0HLM346LL7
KEGG	D08396 Y
ChEBI	CHEBI:8255 Y
ChEMBL	ChEMBL323354 N
CompTox Dashboard (EPA)	DTXSID1045459
ECHA InfoCard	100.046.975
Chemical and physical data
Formula	C22H29N3O6S
Molar mass	463.55 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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 Y Key:ZEMIJUDPLILVNQ-ZXFNITATSA-N Y
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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]