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CHEBI:8255 - pivampicillin

ChEBI IDCHEBI:8255
ChEBI Namepivampicillin
Stars
DefinitionA penicillanic acid ester that is the pivaloyloxymethyl ester of ampicillin. It is a prodrug of ampicillin.
Last Modified14 March 2018
DownloadsMolfile
FormulaC22H29N3O6S
Net Charge0
Average Mass463.556
Monoisotopic Mass463.17771
SMILES[H][C@]12SC(C)(C)[C@H](C(=O)OCOC(=O)C(C)(C)C)N1C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1
InChIInChI=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
InChIKeyZEMIJUDPLILVNQ-ZXFNITATSA-N
Wikipedia
Roles Classification
Biological Role:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
pivampicilinaChemIDplus
pivampicillinChemIDplus
pivampicillineChemIDplus
pivampicillinumChemIDplus
Synonyms  Source
ampicillin pivaloyloxymethyl esterChemIDplus
pivaloyloxymethyl ampicillinateChemIDplus
Manual XrefsDatabases
2218DrugCentral
C11750KEGG COMPOUND
CN101612154Patent
D08396KEGG DRUG
DB01604DrugBank
LSM-6580LINCS
PivampicillinWikipedia
US3660575Patent
Registry NumbersSources
Beilstein:5406076Beilstein
CAS:33817-20-8ChemIDplus
CAS:33817-20-8KEGG COMPOUND
Citations