Synonyms: MK-191 | Pondocillin®
Compound class:
Synthetic organic
Comment: Pivampicillin is a pivaloyloxymethyl ester and prodrug of the β-lactam antibacterial compound ampicillin [1]. It has improved oral bioavailability compared to ampicillin and is rapidly hydrolysed to the active form following absorption from the gastrointestinal tract [3].
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Classification ![]() |
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Compound class | Synthetic organic |
Is prodrug? | Yes |
Active form | ampicillin |
IUPAC Name ![]() |
2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate |
International Nonproprietary Names ![]() |
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INN number | INN |
2864 | pivampicillin |
Synonyms ![]() |
MK-191 | Pondocillin® |
Database Links ![]() |
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Specialist databases | |
Antibiotic DB
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Pivampicillin |
Other databases | |
CAS Registry No. | 33817-20-8 (source: Scifinder) |
ChEBI | CHEBI:8255 |
ChEMBL Ligand | CHEMBL3182343 |
DrugBank Ligand | DB01604 |
DrugCentral Ligand | 2218 |
GtoPdb PubChem SID | 485206041 |
PubChem CID | 33478 |
Search Google for chemical match using the InChIKey | ZEMIJUDPLILVNQ-ZXFNITATSA-N |
Search Google for chemicals with the same backbone | ZEMIJUDPLILVNQ |
Search PubMed clinical trials | pivampicillin |
Search PubMed titles | pivampicillin |
Search PubMed titles/abstracts | pivampicillin |
UniChem Compound Search for chemical match using the InChIKey | ZEMIJUDPLILVNQ-ZXFNITATSA-N |
UniChem Connectivity Search for chemical match using the InChIKey | ZEMIJUDPLILVNQ-ZXFNITATSA-N |