CHEBI:8255 - pivampicillin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name pivampicillin
ChEBI ID CHEBI:8255
Definition A penicillanic acid ester that is the pivaloyloxymethyl ester of ampicillin. It is a prodrug of ampicillin.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C22H29N3O6S
Net Charge 0
Average Mass 463.54828
Monoisotopic Mass 463.178
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
InChIKey ZEMIJUDPLILVNQ-ZXFNITATSA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1)C(=O)OCOC(=O)C(C)(C)C
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing pivampicillin (CHEBI:8255) has functional parent ampicillin (CHEBI:28971)
pivampicillin (CHEBI:8255) has role prodrug (CHEBI:50266)
pivampicillin (CHEBI:8255) is a penicillanic acid ester (CHEBI:51212)
pivampicillin (CHEBI:8255) is a pivaloyloxymethyl ester (CHEBI:136685)
IUPAC Name
[(2,2-dimethylpropanoyl)oxy]methyl 6β-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3α-carboxylate
INNs Sources
pivampicilina ChemIDplus
pivampicillin ChemIDplus
pivampicilline ChemIDplus
pivampicillinum ChemIDplus
Synonyms Sources
ampicillin pivaloyloxymethyl ester ChemIDplus
pivaloyloxymethyl ampicillinate ChemIDplus
Manual Xrefs Databases
2218 DrugCentral
C11750 KEGG COMPOUND
CN101612154 Patent
D08396 KEGG DRUG
DB01604 DrugBank
LSM-6580 LINCS
Pivampicillin Wikipedia
US3660575 Patent
View more database links
Registry Numbers Types Sources
33817-20-8 CAS Registry Number ChemIDplus
5406076 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
10830765 PubMed citation Europe PMC
15793098 PubMed citation Europe PMC
21144541 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
3465515 PubMed citation Europe PMC
Last Modified
14 March 2018