Pivampicillin

Pivampicillin

File:Pivampicillin.svg
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
Routes of administration	Oral
Pharmacokinetic data
Excretion	Renal (76%)
Identifiers
CAS Number	33817-20-8 Y
ATC code	J01CA02 (WHO)
PubChem	CID: 33478
DrugBank	DB01604 Y
ChemSpider	30899 Y
UNII	0HLM346LL7 Y
KEGG	D08396 Y
ChEBI	CHEBI:8255 Y
ChEMBL	CHEMBL323354 N
Chemical data
Formula	C22H29N3O6S
Molecular mass	463.548 g/mol
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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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. 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, it is unlikely to be of clinical significance; long-term use, however, appears problematic and is not recommended.